May 2, 2025

Building in Healthcare : A founders story - Joshua Liu (SeamlessMD)

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Building in Healthcare : A founders story - Joshua Liu (SeamlessMD)

In this episode, we sit down with Josh Lee, Co-founder and CEO of SeamlessMD, a leading platform helping hospitals guide patients through episodes of care. Josh shares his unique journey from medical school to founding a successful healthtech company selling into the complex hospital market. He pulls back the curtain on the realities of healthcare entrepreneurship, from securing those challenging first customers to building a high-performing team and navigating product strategy for scale. If you're interested in healthtech, B2B sales in healthcare, or the founder's path, this episode is packed with valuable insights.

  • (0:00:16) From medical school to founding SeamlessMD: Josh's unconventional journey.
  • (0:05:36) The challenges and realities of building a company in the healthcare space.
  • (0:06:17) The balance of luck and decision-making in startup success.
  • (0:07:35) Identifying and working with different types of hospital customers.
  • (0:10:40) The story and lessons learned from securing the very first hospital pilot.
  • (0:14:51) Key insights and strategies for effective startup hiring.
  • (0:15:53) Moving beyond traditional interviews: the value of practical assessments in hiring.
  • (0:18:47) SeamlessMD's platform approach and the decision to support multiple clinical areas.
  • (0:22:26) Why hospitals prefer a single platform over multiple point solutions.
  • (0:35:33) Raising capital: ensuring funding solves the right problems (not just lack of product-market fit).
  • (0:37:39) Achieving and maintaining product-market fit in a dynamic market.
  • (0:43:50) Competing with large incumbents like EMR systems.
  • (0:47:40) The role and potential of AI in healthcare and SeamlessMD's approach.
  • (0:39:30) Navigating work-life balance as a founder (work-life harmony).
  • (0:51:35) Final advice for aspiring healthcare entrepreneurs.

WEBVTT

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would love for you to give an introduction on

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yourself to our audience, and then we'll take

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it from there. Cool. So hey, everyone, my name

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is Josh Lee, one of the founders and the CEO

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of seamless MD. Probably my real story starts

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over 10, maybe 15 years ago. So when I did my

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undergrad, I didn't know what I well, I'll back

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up. I was planning to go into medicine, which

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I ended up doing. But I think that was largely

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because that was sort of the traditional path

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that I had envisioned for myself, having gone

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through the sciences and all that. But even during

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undergrad, I would question whether or not I

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should do med school in the first place. I remember

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one time I was just talking to my dad when I

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was an undergrad, and I wasn't really enjoying

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school that much. And I said, Hey, like, what

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if I decided to just drop out of school and like

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go do something totally different? And, you know,

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he was silent for a minute. And then afterwards,

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he said, You know what, whatever you do, I'll

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support you. And I was like, Oh, my gosh, well,

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that didn't happen. I basically didn't find something

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better to do during undergrad. So I stayed on

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the med school path, did med school. But even

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then I was still lost. A lot of my colleagues

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knew that they wanted to go into family medicine

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or surgery or something else. I did not have

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that clarity whatsoever. But I got lucky because

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I had some fantastic mentors who said, hey, Josh,

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why don't you come spend a summer with us doing

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research, not on clinical things, but on broader

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health care system challenges around quality

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and safety and cost. I ended up doing research

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on preventing readmissions back to hospital.

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And that got me really energized, I think, for

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the first time in medical school. And then around

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that time, and this is kind of back in, let's

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say, 2011 or so, I started getting interested

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in tech and startups. I'm not sure why maybe

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just random stuff I was seeing on social media.

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But I ended up actually trying to start a totally

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different healthcare tech venture. with two friends

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from med school. And we quit slash gave up after

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four to five months. And I think one of the big

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reasons for that was, yeah, we were busy with

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med school, but we were all clinical people,

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you know, none of us knew how to write code,

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build a product, etc. So we had overlapping skill

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sets. And then my last year of med school, I

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still had the itch to build something. And on

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a whim, I applied to the next 36, which is a

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startup incubator in Toronto. And what was unique

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about this incubator at the time, at least was

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you didn't enter the incubator with a fully formed

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team or startup, you actually applied as an individual

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and they would connect you with other potential

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founders. And so I actually met my co -founders

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through the next 36 who were both brilliant engineers.

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We were all interested in healthcare. And I brought

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the readmissions problem to the team and said,

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Hey, you know, like, this is a big problem. You

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could we build tech to better support and manage

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patients outside the hospital to prevent something

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like a readmission. And we launched our current

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ventures theme SMD through that incubator. While

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we were all in our last year of school myself,

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my last year of med school, I graduated, got

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into residency. but never started it because

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I ended up going full -time on the company. And

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for the last 12 years, building this company

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has been my full -time job. I actually never

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started residency. And so despite that though,

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if not for medical school, I would not be building

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the venture today. But I hope that gives people

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at least some good background to how I got into

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you know, healthcare entrepreneurship, but happy

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to take this conversation wherever you'd like,

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Rashad. That's a very interesting choice you

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made and one that most people would not make.

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And one I would probably advise against making

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for medical students. If a med student came to

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you and said, Josh, I have this venture, it's

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in the current hot thing, AI agents for healthcare

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space. What advice would you give them? And would

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you advise them to not pursue residency and pursue

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their venture instead? Yeah, I think my advice

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by level is people should follow their curiosity.

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So I would say, hey, if you want to go pursue

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and learn and build something in the AI agent

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or any other space, you should do that. It doesn't

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mean you have to leave score training, right?

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There's no reason why if you can find the time

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you can learn and build and do stuff on the side,

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not easy, but certainly possible. And a lot of

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ventures, as you know, started off as side projects.

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And it may stay as just a project or at some

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point it may make sense because either. you want

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to go bigger, and you know you need to give it

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your full attention and turn it into a full -time

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venture. Great. You can do that. But I don't

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think it has to be decided upfront. Is this a

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full -time venture or nothing? I don't think

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it's a binary thing. I think you could start

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as a side project and then decide from there.

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That would be my advice. Now, at the same time,

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though, I would always caution potential entrepreneurs,

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hey, healthcare is really hard. It's really slow,

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et cetera, et cetera. And frankly, If telling

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you that convinces you not to pursue a venture,

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it probably wasn't going to be the right fit

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for you anyways. But for the people who hear

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that and go, yeah, that's fine. I'm going to

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build it anyways. OK, then you know what? You're

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probably meant to build this because it doesn't

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matter what I say. You're going to just keep

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going for it anyways, which is fantastic. You

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should go do it. How much of your success do

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you think is luck versus decisions you've made?

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I think it's hard to quantify. I think both play

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significant role. I think the reality is, when

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I think about good decisions I've made, probably

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I would say on average 60 % good, 40 % bad. And

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I think it's like, you generally need to make

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more good decisions than bad ones. You generally

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need to make better decisions for the more important,

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you know, impactful decisions that you may have.

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But at the same time, though, part of it is just

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surviving long enough so that way, you don't

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get killed by the bad decisions and you are out

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enough for the good decisions to pay off. Because,

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you know, a lot of times, like even for good

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decisions, like luck plays a significant role.

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I mean, we talked through many different situations

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like that. But but both play a role. It's hard.

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It's hard for me to separate the two and quantify

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it, though. Talk to me about the best customer

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you've had, and obviously you don't have to name

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names, and the worst customer you've had. And

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were there some signals or signs that this is

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going to be an easy organization to work with

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versus a difficult organization, and maybe it's

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not worth it? Yeah, so I would say in our experience,

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and I'm coming from the digital health, so software

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world. you know, the answer might be different

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depending on the product or the venture. But

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I would say for us, the most difficult customers

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have been the ones where they've prioritized

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the research aspect of the innovation over the

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practical deployment aspect. So for example,

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you know, we had an organization many years ago

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where they would bring seamless MD in. And normally

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when we implement the product, we have a whole

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implementation and success team that project

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manages the whole process that manages the relationship,

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makes it successful, works closely with the clinical

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teams and the operation of folks. And we run

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a whole playbook to make it a successful partnership.

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But this was a case where the health system wanted

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to run it purely as a research study. They had

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assigned study coordinators who wanted to control

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everything, wouldn't let our team be that involved

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in the process. wouldn't let our team interface

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with the clinicians after the implementation.

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And so unsurprisingly, it didn't go very well

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because we weren't able to run the playbook.

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And the reality is, when it comes to healthcare

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technology, the tech is one thing, but the people

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and the process and the change management are

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critical elements where if not done well, the

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thing could go poorly. If done well, the thing

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could go great. And we weren't able to impact

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the people in the process side as much as we

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normally do. And I think part of that is when

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folks care too much about the research and not

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about, hey, how do we make this successful as

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an initiative and the organization and drive

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real results? Our best customer partners are

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the ones who don't really focus on their research

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and just say, hey, Seamless, you've done this

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many times before. What do you need to make this

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successful? and we're willing to invest the people

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and the resources. So that typically means the

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leadership team has to be bought in and engaged.

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People have to show up to regular checkpoints.

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People have to troubleshoot with us. They have

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to care about the outcomes. They have to care

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to monitor the data. And it doesn't mean they

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never do research, but I would say they tend

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to focus on let's make this technology successful.

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And sure, we'll do retrospective analyses to

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make sure that we're improving outcomes. But

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that's not the reason why we're doing this. We're

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doing this with the intent to make it work, not

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to hope that it works in a very controlled study

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setting. Because as you know, the study setting

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is not at all like the real world setting either

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a lot of the time. Yeah. And I think this has

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led to extrapolating from the study setting and

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then creating guidelines. different expert advice

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that states that this is how we should do things.

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It's led to some distrust of medicine as well,

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but we'll leave that for a different discussion.

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Talk to me about your first sale and how did

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you approach the organization and why do you

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think you were successful? And maybe talk to

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me about some sales that you weren't successful

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with and what could you have changed to close

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it? So it's funny, when you say first sale, I'm

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trying to think through my head, how I even define

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that because, you know, I could tell you about

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like the first few pilots where it's a sale on

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that it got into the institution, but it wasn't

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much of a sale of, you know, there really wasn't

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much of a dollar value attached to it. And as

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you know, as you get more mature as a company,

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especially in healthcare, you do less of these

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pilots or free pilots and more of these actual

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sales and mature deployments, but I can tell

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you our very first, you know, implementation

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at least, which was more like a free pilot was

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still a lot of work, right? Like, this was back

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in, you know, let's call it early 2013. We had,

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we had a prototype and not much of a product.

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We had no proof points, no traction, nothing.

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And, you know, I just, you know, code emailed

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a couple of surgeons who were who are doing research

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actually on preventing readmissions. And people,

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people took my call. And we were lucky that we

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found some early adopters who said, Oh, this

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is awesome. Let's try this, which by the way,

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is very different than today where people get

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so much email. Now, as you know, there's so much

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noise in the inbox that it's very hard to get

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through to people back then like you didn't have

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a million you know startups emailing everyone

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right so back then people got fewer emails they'd

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read everything they'd engage um but it took

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us 12 months to even just get a free pilot signed

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with the institution um and it's crazy to me

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because when i think about um how strapped startups

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are for for not just people resources but but

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money and support if if i were to tell myself

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back then hey it would be 12 months before you

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got your first user actually trying the product.

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I don't know if I would have signed up for this,

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right? That's a crazy amount of time for a startup

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to get its first user and not even a paying user,

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by the way. So I think we were, I think we were

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lucky to have been, you know, first time naive

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entrepreneurs who didn't know any better because

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then you can tell yourself, Hey, like it's just

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around the corner. It's coming anytime now. It's

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just part of the process. I mean, now it would

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probably drive me crazy that it took 12 months

00:13:18.740 --> 00:13:21.620
just to get a user, you know what I mean? And

00:13:21.620 --> 00:13:25.139
do you find the ecosystem has evolved where now

00:13:25.139 --> 00:13:27.860
it doesn't take 12 months? And if so, what's

00:13:27.860 --> 00:13:32.179
changed in the ecosystem? Yeah, I think probably

00:13:32.179 --> 00:13:34.139
there's a lot more maturity in just being comfortable

00:13:34.139 --> 00:13:37.200
with third -party software products. I mean,

00:13:37.200 --> 00:13:40.600
especially cloud -based products that are not

00:13:40.600 --> 00:13:45.279
installed on -premise. Even back in 2012, cloud

00:13:45.279 --> 00:13:47.460
was not technically new, but I don't think there

00:13:47.460 --> 00:13:50.620
were that many third -party cloud -based solutions

00:13:50.620 --> 00:13:54.440
being used at hospitals and health systems. That

00:13:54.440 --> 00:13:56.220
was probably part of the challenge, getting people

00:13:56.220 --> 00:13:59.320
comfortable with that concept. The other challenge

00:13:59.320 --> 00:14:01.860
we had back then was we were initially back then

00:14:01.860 --> 00:14:05.799
a mobile -only software product. And back in

00:14:05.799 --> 00:14:11.679
2013, only, let's say, 50 % of Americans or Canadians

00:14:12.039 --> 00:14:14.600
had access to a smartphone. And so we had a lot

00:14:14.600 --> 00:14:17.399
more pushback back then around a mobile first

00:14:17.399 --> 00:14:19.659
product. Now we're obviously multi -channel,

00:14:19.940 --> 00:14:22.299
and now penetration is over 90 % for mobile.

00:14:22.399 --> 00:14:25.659
It's much better. But back then, it just wasn't

00:14:25.659 --> 00:14:28.440
as accessible a product. So I'm actually looking

00:14:28.440 --> 00:14:31.740
back kind of surprised that we even got anyone

00:14:31.740 --> 00:14:36.000
working with us. But I can see why looking back,

00:14:36.120 --> 00:14:39.220
it was not an obvious solution to have. In fact,

00:14:39.740 --> 00:14:41.860
if I were working at the hospital, I probably

00:14:41.860 --> 00:14:44.919
would have pushed back on this product now that

00:14:44.919 --> 00:14:47.860
I think about it. I'm happy not everyone did,

00:14:47.919 --> 00:14:51.039
and you had some of the adopters. One of the

00:14:51.039 --> 00:14:54.299
hardest things about growing a startup is knowing

00:14:54.299 --> 00:14:57.720
who to hire and kind of honing down your hiring

00:14:57.720 --> 00:15:00.620
process. Talk to me about your hiring process,

00:15:00.659 --> 00:15:03.940
and if you can talk maybe about the best hire

00:15:03.940 --> 00:15:06.700
you've had and also a bad hire you had to let

00:15:06.700 --> 00:15:13.240
go of. Yeah, so I think I'll share a couple of

00:15:13.240 --> 00:15:14.799
the biggest things I've learned about the hiring

00:15:14.799 --> 00:15:19.559
process. I think one of the things that ends

00:15:19.559 --> 00:15:23.059
up being difficult about the hiring process is

00:15:23.059 --> 00:15:27.399
a lot of the traditional methods, I think, don't

00:15:27.399 --> 00:15:31.799
very well capture the information we actually

00:15:31.799 --> 00:15:34.539
need to make a good decision. So, you know, one

00:15:34.539 --> 00:15:36.379
of the things that you care about as a company

00:15:36.379 --> 00:15:39.950
is, well, you know, what is that person's actual

00:15:39.950 --> 00:15:43.490
performance gonna be like? And the reality is

00:15:43.490 --> 00:15:47.009
an interview helps you assess communication skills,

00:15:47.049 --> 00:15:49.330
but it doesn't actually assess performance on

00:15:49.330 --> 00:15:53.309
specific competencies, right? So interviewing

00:15:53.309 --> 00:15:56.009
an engineer purely verbally will not tell you

00:15:56.009 --> 00:15:59.269
much about their ability to code, right? Or even

00:15:59.269 --> 00:16:01.509
interviewing a salesperson, yeah, you could see

00:16:01.509 --> 00:16:03.690
if they had decent communication skills, but

00:16:03.690 --> 00:16:06.429
that tells you nothing about how would they actually...

00:16:07.539 --> 00:16:11.059
do customer discovery or do a big sales presentation

00:16:11.059 --> 00:16:15.539
or negotiate something. And so one of the biggest

00:16:15.539 --> 00:16:19.740
success tools we've used is actually as part

00:16:19.740 --> 00:16:23.240
of the hiring process, have the person do some

00:16:23.240 --> 00:16:27.000
sort of assessment that's reasonably close to

00:16:27.000 --> 00:16:28.580
the type of work they're doing here and see how

00:16:28.580 --> 00:16:32.460
they do. So for example, if we're hiring a salesperson,

00:16:32.600 --> 00:16:35.210
we'll have them We will actually give them, hey,

00:16:35.450 --> 00:16:37.730
here's like a scenario, like an event. We're

00:16:37.730 --> 00:16:40.190
going to give you a scenario with you work here

00:16:40.190 --> 00:16:44.490
at Seamless. Here's a hypothetical customer that

00:16:44.490 --> 00:16:47.110
you're going to meet. Here's their current situation.

00:16:48.529 --> 00:16:51.169
And you're going to pretend that you're presenting

00:16:51.169 --> 00:16:56.450
to the head of surgery and the COO of the hospital

00:16:56.450 --> 00:16:59.009
and one other person. And we're going to spend

00:16:59.009 --> 00:17:01.409
30 minutes with you role playing being a salesperson

00:17:01.409 --> 00:17:03.679
at Seamless presenting. us role -playing the

00:17:03.679 --> 00:17:06.079
potential customer and having dialogue about

00:17:06.079 --> 00:17:10.440
it. And what's powerful about these assignments

00:17:10.440 --> 00:17:13.960
are that it tells you a lot. So for one is how

00:17:13.960 --> 00:17:17.220
prepared the person is for that sales presentation

00:17:17.220 --> 00:17:20.119
tells you a lot about the effort they'll put

00:17:20.119 --> 00:17:23.660
into anything they do. So we've had people who

00:17:23.660 --> 00:17:26.660
basically showed up like totally unprepared,

00:17:27.259 --> 00:17:29.200
which is like an indication of like what would

00:17:29.200 --> 00:17:32.509
happen in real life. We've had others, when I

00:17:32.509 --> 00:17:34.089
asked them afterwards, how many hours did you

00:17:34.089 --> 00:17:37.029
prepare for this? And one person told me, who

00:17:37.029 --> 00:17:40.029
did a great job, by the way, told me 10 hours.

00:17:40.549 --> 00:17:42.250
And that was not a requirement. We don't ask

00:17:42.250 --> 00:17:45.329
people to prepare a certain amount of things.

00:17:46.069 --> 00:17:48.230
We intentionally don't even give them that much

00:17:48.230 --> 00:17:50.589
of a guideline around how to prepare, because

00:17:50.589 --> 00:17:53.390
we want to know what they would do, what kind

00:17:53.390 --> 00:17:56.849
of initiative and agency they have. And so I'm

00:17:56.849 --> 00:17:59.009
always surprised by how there are people with

00:17:59.009 --> 00:18:03.269
fantastic resumes who totally bomb the assignment

00:18:03.269 --> 00:18:07.190
part and others who are just like who are early

00:18:07.190 --> 00:18:09.410
in their career, have less of a track record,

00:18:09.410 --> 00:18:13.170
but do so much better on this. And we've seen

00:18:13.170 --> 00:18:15.609
very high correlation between performance on

00:18:15.609 --> 00:18:18.869
these sort of assessment assignments and actual

00:18:18.869 --> 00:18:21.029
performance at the company. And I think the other

00:18:21.029 --> 00:18:23.210
biggest thing we find is that the people who

00:18:23.210 --> 00:18:27.650
are really good They can't help but be excellent

00:18:27.650 --> 00:18:30.390
at any work that they want to output. They can't

00:18:30.390 --> 00:18:32.390
help but do a great job on the presentation.

00:18:32.769 --> 00:18:36.630
It would kill them to do a bad job. And it shows

00:18:36.630 --> 00:18:39.190
the quality of work they even do in this random

00:18:39.190 --> 00:18:42.349
assignment in the interview process. I've got

00:18:42.349 --> 00:18:47.609
more, but I'll stop there. Yeah. Yeah. SeamlessMD

00:18:47.609 --> 00:18:52.180
has a few different products. and reducing readmission

00:18:52.180 --> 00:18:54.619
rates, it seems like that's the key metric, but

00:18:54.619 --> 00:18:56.599
you also work with surgeries and post -surgical

00:18:56.599 --> 00:19:00.259
follow -up. Is everything under the umbrella

00:19:00.259 --> 00:19:04.200
of reducing readmission rates? And how do you

00:19:04.200 --> 00:19:07.480
decide what product to focus on first? Is it

00:19:07.480 --> 00:19:12.519
more of a customer -led kind of process or? Yeah,

00:19:12.680 --> 00:19:15.480
so we have a single flexible platform that works

00:19:15.480 --> 00:19:18.700
for many different. um surgical procedures or

00:19:18.700 --> 00:19:20.680
health conditions so we can support anything

00:19:20.680 --> 00:19:23.500
from like orthopedic surgery to the pregnancy

00:19:23.500 --> 00:19:26.240
journey to the cancer journey to chronic care

00:19:26.240 --> 00:19:29.720
and everything in between and so um when we work

00:19:29.720 --> 00:19:31.819
with the health system we not only determine

00:19:31.819 --> 00:19:33.940
okay what are the conditions or procedures we

00:19:33.940 --> 00:19:37.859
cover within a specific clinical area we work

00:19:37.859 --> 00:19:41.240
with the clinical and operational staff to understand

00:19:41.240 --> 00:19:44.259
well what are the kpis your program cares about

00:19:44.259 --> 00:19:46.950
so it could be the case that you know, orthopedics

00:19:46.950 --> 00:19:49.849
in one hospital wants to reduce readmissions.

00:19:50.269 --> 00:19:52.890
And so we'll kind of configure the workflows

00:19:52.890 --> 00:19:55.750
and implementation to focus on that. But there's

00:19:55.750 --> 00:19:57.849
another orthopedic program and a different customer

00:19:57.849 --> 00:19:59.390
who might say, well, I'm trying to reduce length

00:19:59.390 --> 00:20:03.970
of stay. And so it's the it's generally the same

00:20:03.970 --> 00:20:07.549
technical platform. The clinical side gets configured

00:20:07.549 --> 00:20:10.930
based on the specific specialty and then the

00:20:10.930 --> 00:20:12.990
workflows and the implementation approach and

00:20:12.990 --> 00:20:15.750
how we support them. look at further kind of

00:20:15.750 --> 00:20:17.430
tailored based on what goals they want to achieve.

00:20:18.390 --> 00:20:20.690
And sometimes it's like, I want to reduce like

00:20:20.690 --> 00:20:25.130
all the above and that happens too. And what

00:20:25.130 --> 00:20:30.190
was this? So the usual advice is, you know, focus

00:20:30.190 --> 00:20:33.089
on one specific thing and get really good at

00:20:33.089 --> 00:20:35.690
that and then expand to, you know, so maybe focus

00:20:35.690 --> 00:20:38.569
on hip surgery, length of stay, and that's all

00:20:38.569 --> 00:20:41.289
you do. Don't worry about readmission rates.

00:20:41.410 --> 00:20:43.509
Don't worry about length of stay for knee surgery.

00:20:43.960 --> 00:20:46.019
or for shoulder surgery, or for heart failure,

00:20:46.140 --> 00:20:48.740
or for COPD, just focus on one thing. It seems

00:20:48.740 --> 00:20:52.460
like you did follow that advice, and you have

00:20:52.460 --> 00:20:55.279
been successful, it seems like, partly because

00:20:55.279 --> 00:20:58.299
you didn't follow that advice. Tell me about

00:20:58.299 --> 00:21:00.819
what your thoughts are on, you know, what would

00:21:00.819 --> 00:21:03.680
have happened if you said, all I'm doing is length

00:21:03.680 --> 00:21:07.359
of stay for hip replacements? Yeah, so what's

00:21:07.359 --> 00:21:09.819
interesting is that we went back and forth on

00:21:09.819 --> 00:21:12.859
that for many years, right? So we had moments

00:21:12.859 --> 00:21:15.920
where we said, Hey, we should, let's say, only

00:21:15.920 --> 00:21:19.599
do orthopedics, be world class orthopedics, get

00:21:19.599 --> 00:21:23.400
orthopedics in every single institution, let's

00:21:23.400 --> 00:21:26.799
say North America. And then, and then from there,

00:21:26.839 --> 00:21:29.579
then start to expand into, you know, cardiovascular,

00:21:30.000 --> 00:21:31.880
and then get and they get every cardiovascular

00:21:31.880 --> 00:21:34.039
program using it and then later expand to women's

00:21:34.039 --> 00:21:36.400
health, then basically almost like verticalize

00:21:36.400 --> 00:21:38.960
each one and then grow horizontally across the

00:21:38.960 --> 00:21:43.289
health system. We ended up not doing that. We

00:21:43.289 --> 00:21:46.849
ended up actually going down the whole land and

00:21:46.849 --> 00:21:49.829
expand route where, hey, we might start in orthopedics,

00:21:50.089 --> 00:21:53.069
but we might start in cardiac, or we might start

00:21:53.069 --> 00:21:55.289
in women's health. And part of the reason for

00:21:55.289 --> 00:21:58.230
that was it was hard to predict, depending on

00:21:58.230 --> 00:22:00.069
the health system, what would be the first one

00:22:00.069 --> 00:22:03.069
or two use cases that they wanted to start with.

00:22:03.150 --> 00:22:04.849
Now, there tends to be a common set, but it's

00:22:04.849 --> 00:22:08.930
never just orthopedics. And if we if we refuse

00:22:08.930 --> 00:22:10.450
to do that said no no no we're only going to

00:22:10.450 --> 00:22:13.190
do orthopedics. Then we would lose that initial

00:22:13.190 --> 00:22:15.109
we lose a customer to someone else was willing

00:22:15.109 --> 00:22:18.170
to start in cardiac for example. And so we had

00:22:18.170 --> 00:22:20.849
we realized we had to be flexible and broad enough

00:22:20.849 --> 00:22:23.569
that we could support whatever use cases health

00:22:23.569 --> 00:22:26.750
systems want to go with first. But then the other

00:22:26.750 --> 00:22:29.329
thing that we uncovered was that health systems

00:22:29.329 --> 00:22:33.329
over time just want one. Platform partner for

00:22:33.329 --> 00:22:35.529
all the conditions because they didn't want.

00:22:35.759 --> 00:22:38.460
a fragmented patient user experience where there

00:22:38.460 --> 00:22:40.480
could be a hundred different point solutions

00:22:40.480 --> 00:22:42.680
that all look and feel different for the same

00:22:42.680 --> 00:22:45.339
use case, just in different clinical areas. And

00:22:45.339 --> 00:22:47.440
so I can tell you, we have some competitors where

00:22:47.440 --> 00:22:50.900
they're world -class at one solution like orthopedics

00:22:50.900 --> 00:22:52.759
or women's health or cardiology or something.

00:22:53.359 --> 00:22:55.859
And their struggle has been that, you know, they

00:22:55.859 --> 00:22:58.039
get pigeonholed into being, well, you're only

00:22:58.039 --> 00:23:01.220
an orthopedic solution. Our health system needs

00:23:01.220 --> 00:23:04.640
an enterprise product and Yes, seamless orthopedics

00:23:04.640 --> 00:23:08.259
might only be 80 % of what you do in ortho, but

00:23:08.259 --> 00:23:10.920
seamless is 80 % for every single specialty.

00:23:11.099 --> 00:23:15.079
I'd rather have that than 100 % in ortho and

00:23:15.079 --> 00:23:17.880
then needing to buy 99 other products. And so

00:23:17.880 --> 00:23:20.059
once we understood that from the customer perspective,

00:23:20.339 --> 00:23:22.259
we had a clear path to, okay, we got to be a

00:23:22.259 --> 00:23:24.059
platform product. We got to support everything,

00:23:24.059 --> 00:23:27.900
which is not easy, but that's the only path to

00:23:27.900 --> 00:23:30.240
winning the long -term partnership and making

00:23:30.240 --> 00:23:34.099
it manageable for the health system. Let's go

00:23:34.099 --> 00:23:36.500
back to your hiring process. I'd love for you

00:23:36.500 --> 00:23:40.700
to talk me through what it looks like from the

00:23:40.700 --> 00:23:45.180
idea comes to you where we need a CEO or a CFO,

00:23:45.759 --> 00:23:49.200
or we need a new sales rep. And I realize there

00:23:49.200 --> 00:23:52.599
are two different hiring processes. What's the

00:23:52.599 --> 00:23:55.759
path from that idea in your brain to someone

00:23:55.759 --> 00:24:00.839
physically working for you? Yeah, so step one.

00:24:00.920 --> 00:24:03.259
And I'm annoying about this now, but it's all

00:24:03.259 --> 00:24:06.059
about whether it's hiring or some other initiative.

00:24:07.160 --> 00:24:09.220
Is there a problem to actually be solved first

00:24:09.220 --> 00:24:12.259
and foremost? And the number two, does this solution

00:24:12.259 --> 00:24:15.079
which might be hiring someone actually solve

00:24:15.079 --> 00:24:18.559
the problem? Because to your example there for

00:24:18.559 --> 00:24:22.079
sales, right? I think there's often a misconception

00:24:22.079 --> 00:24:25.700
that the solution to sales is to hire more sales

00:24:25.700 --> 00:24:29.430
reps. That might be the answer. but it might

00:24:29.430 --> 00:24:31.990
not be depending on the root cause of why sales

00:24:31.990 --> 00:24:34.970
are not growing as quickly as you want. So we

00:24:34.970 --> 00:24:36.470
can park that conversation because that might

00:24:36.470 --> 00:24:38.650
be a whole other interesting topic of when does

00:24:38.650 --> 00:24:41.130
it make sense to even hire a salesperson. But

00:24:41.130 --> 00:24:44.710
once you've decided that, yes, the right solution

00:24:44.710 --> 00:24:49.009
for this problem that exists is to hire someone,

00:24:49.509 --> 00:24:52.509
then it comes down to, okay, do we actually know

00:24:52.509 --> 00:24:56.470
the right profile of the right hire for this?

00:24:56.759 --> 00:24:59.039
And so kind of what I advise folks now is to

00:24:59.039 --> 00:25:02.339
come up with almost like a hiring scorecard for,

00:25:02.460 --> 00:25:06.839
OK, for this role, what are the important traits,

00:25:08.240 --> 00:25:11.759
track record items that the person has to have?

00:25:11.839 --> 00:25:14.119
And then very importantly, what does success

00:25:14.119 --> 00:25:17.279
look like six, 12 months after the hire? Because

00:25:17.279 --> 00:25:22.220
we have to know what we're hiring for. And then

00:25:22.220 --> 00:25:25.950
once you build that out, then you go down to

00:25:25.950 --> 00:25:30.390
actually sourcing and bring the right people

00:25:30.390 --> 00:25:33.470
into that funnel. But if you don't do that upfront

00:25:33.470 --> 00:25:35.869
work right, you tend to end up bringing the wrong

00:25:35.869 --> 00:25:37.670
people into the funnel. And then people have

00:25:37.670 --> 00:25:42.029
no idea how to screen people properly. And then

00:25:42.029 --> 00:25:43.869
once you're actually bringing people in, I think

00:25:43.869 --> 00:25:47.049
a very important thing is realizing that interviewing

00:25:47.049 --> 00:25:50.809
is a two -way process. So let's say there's a

00:25:50.809 --> 00:25:53.920
role that I am personally hiring for. and I'm

00:25:53.920 --> 00:25:55.980
managing the process, I'm taking the first call,

00:25:56.140 --> 00:25:58.359
et cetera, et cetera. Typically in that first

00:25:58.359 --> 00:26:04.039
call, I intentionally share a bit about myself

00:26:04.039 --> 00:26:07.079
and Seamless First. And before even asking them

00:26:07.079 --> 00:26:10.420
about themselves, I say, hey, do you have any

00:26:10.420 --> 00:26:13.319
questions about Seamless or the role or anything?

00:26:13.940 --> 00:26:16.859
I do that for a few reasons. One is I'm putting

00:26:16.859 --> 00:26:19.900
the effort to sell Seamless First and giving

00:26:19.900 --> 00:26:23.000
them a chance to get educated. But two is, What

00:26:23.000 --> 00:26:24.660
I found is that there's a very hard correlation

00:26:24.660 --> 00:26:27.619
between the quality of the questions that the

00:26:27.619 --> 00:26:30.460
candidate asked me and how good of a candidate

00:26:30.460 --> 00:26:33.259
they are. So our best hires are people where

00:26:33.259 --> 00:26:36.039
in that first call, like they are grilling me.

00:26:36.299 --> 00:26:38.920
They are asking me really tough, complicated

00:26:38.920 --> 00:26:41.599
questions about seamless. They're like, who are

00:26:41.599 --> 00:26:44.440
your biggest competitors? How are you differentiated?

00:26:45.039 --> 00:26:47.720
How are you thinking about your roadmap? Tell

00:26:47.720 --> 00:26:50.339
me more about the market. What's the most difficult?

00:26:50.519 --> 00:26:53.319
part about selling the product right now. They're

00:26:53.319 --> 00:26:56.140
grilling me and I love that. I'm like, oh my

00:26:56.140 --> 00:26:57.819
God, they're intellectually curious, they're

00:26:57.819 --> 00:27:00.240
smart, they're already thinking about the business

00:27:00.240 --> 00:27:03.940
because that shows me the types of questions

00:27:03.940 --> 00:27:06.039
and intellectual curiosity they will bring into

00:27:06.039 --> 00:27:09.640
the team. The lowest performing candidates have

00:27:09.640 --> 00:27:12.119
been ones who are like, have no questions or

00:27:12.119 --> 00:27:15.160
asking me things like, oh, so like, is there

00:27:15.160 --> 00:27:19.119
an office? you know, like, like super basic things

00:27:19.119 --> 00:27:21.519
that show no curiosity about the actual business.

00:27:21.720 --> 00:27:24.099
And so they don't realize it, but I'm actually

00:27:24.099 --> 00:27:25.980
evaluating them from the moment they actually

00:27:25.980 --> 00:27:28.400
start asking me questions. Cause I've found very

00:27:28.400 --> 00:27:31.559
high signal in that data. And then from there,

00:27:31.619 --> 00:27:33.140
I started asking them questions. I have a list

00:27:33.140 --> 00:27:34.779
of like screening questions based on what I'm

00:27:34.779 --> 00:27:37.039
looking for, but I could tell pretty quickly

00:27:37.039 --> 00:27:38.740
early on, like based on that, even that first

00:27:38.740 --> 00:27:41.740
interaction, like how likely it's going to be

00:27:41.740 --> 00:27:44.079
a good fit, just based on And I think maybe because

00:27:44.079 --> 00:27:46.000
we just care about curiosity in our company.

00:27:46.740 --> 00:27:49.920
But but that's a very big signal. And then we

00:27:49.920 --> 00:27:52.079
have a whole like we have a screening process,

00:27:52.079 --> 00:27:55.039
the assignment, we have like, I can go more detail

00:27:55.039 --> 00:27:56.759
if you want, we've interviews with our team members.

00:27:57.119 --> 00:28:00.380
But I think I would say the first screening conversation

00:28:00.380 --> 00:28:03.160
and their curiosity, the assignment. And then

00:28:03.160 --> 00:28:04.940
the last piece, I think that's very big is actually

00:28:04.940 --> 00:28:08.640
the reference calls. And not even necessarily

00:28:08.640 --> 00:28:11.759
the ones they give you, if you can kind of as

00:28:11.759 --> 00:28:15.160
you probably know, like you can backchannel references

00:28:15.160 --> 00:28:18.819
and get candid information. Or even if it's not

00:28:18.819 --> 00:28:21.079
backchanneled, doing references the right way

00:28:21.079 --> 00:28:23.539
with the references they give you, that makes

00:28:23.539 --> 00:28:26.279
all the difference. Because I think what we found

00:28:26.279 --> 00:28:30.339
is that what other people tell you about their

00:28:30.339 --> 00:28:33.539
performance and how they get compared, gives

00:28:33.539 --> 00:28:36.599
you more signal than most of the things they

00:28:36.599 --> 00:28:37.880
would tell you about themselves in the interview.

00:28:38.019 --> 00:28:39.480
Because everyone who's reasonably good at interviewing,

00:28:39.619 --> 00:28:42.259
especially executives, Like know the right things

00:28:42.259 --> 00:28:45.680
to say. Like the people who are executives are

00:28:45.680 --> 00:28:48.019
so seasoned in an actual conversation that you

00:28:48.019 --> 00:28:49.680
don't learn that much in the interview actually

00:28:49.680 --> 00:28:53.180
in terms of the traditional interview. But like,

00:28:53.259 --> 00:28:55.279
do they show up for the assignment? Like I'll

00:28:55.279 --> 00:28:57.359
put executives through an assignment and some

00:28:57.359 --> 00:29:01.259
will just like completely implode or not care

00:29:01.259 --> 00:29:03.400
and not put any effort into it. You'd be surprised.

00:29:04.319 --> 00:29:08.880
Do you think it would make sense to do the interview

00:29:08.880 --> 00:29:12.789
last? once you've kind of almost made the decision.

00:29:13.250 --> 00:29:15.890
Because there are people who are very charming,

00:29:17.049 --> 00:29:19.569
who can charm themselves through an interview.

00:29:21.049 --> 00:29:23.950
And it's almost as if the interview is just to

00:29:23.950 --> 00:29:27.069
evaluate to see if you can hold a conversation

00:29:27.069 --> 00:29:29.190
and have okay communication skills. But as you

00:29:29.190 --> 00:29:32.750
said, it doesn't, it's not an indicator of performance.

00:29:33.690 --> 00:29:35.769
So it's fascinating. Yeah, it's fascinating because

00:29:35.769 --> 00:29:39.069
like, if you don't have a traditional interview

00:29:39.069 --> 00:29:42.130
component where you ask about like their background,

00:29:42.250 --> 00:29:44.549
their upbringing, like their hobbies, whatever,

00:29:44.990 --> 00:29:47.490
it kind of feels like you don't care about them

00:29:47.490 --> 00:29:50.210
on a personal level. But it's interesting because

00:29:50.210 --> 00:29:52.490
what I found is that the biggest signal comes

00:29:52.490 --> 00:29:54.650
from like almost like non -personal things. It's

00:29:54.650 --> 00:29:57.809
like, like, like how they like when they actually

00:29:57.809 --> 00:30:00.710
do the assignment or when they ask us about the

00:30:00.710 --> 00:30:02.609
company or they give us feedback on what they

00:30:02.609 --> 00:30:04.009
would do if they worked here, like all of those

00:30:04.009 --> 00:30:06.970
have been better signals to us than their hobbies.

00:30:07.359 --> 00:30:10.380
or like, you know, what their upbringing was

00:30:10.380 --> 00:30:12.980
like and all these other things. I would say

00:30:12.980 --> 00:30:15.319
the difference is that if they are early in their

00:30:15.319 --> 00:30:18.380
career with not much of a professional track

00:30:18.380 --> 00:30:23.400
record, then how they did in like school tends

00:30:23.400 --> 00:30:26.920
to be more useful. But if someone has like a

00:30:26.920 --> 00:30:28.859
20 year track record, and they're an executive

00:30:28.859 --> 00:30:32.500
hire, like, I don't learn that much from what

00:30:32.500 --> 00:30:34.240
they did 30 years ago, and they're like their

00:30:34.240 --> 00:30:37.299
whole life story. That's just been been our experience

00:30:37.299 --> 00:30:41.799
though So if someone is a has a 30 -year track

00:30:41.799 --> 00:30:45.140
record, how do you evaluate them? It's all the

00:30:45.140 --> 00:30:47.559
other things I mentioned. So it's it's it's how

00:30:47.559 --> 00:30:49.259
intoxicated curious they are. How good are their

00:30:49.259 --> 00:30:52.079
questions? the other thing that I do with an

00:30:52.079 --> 00:30:55.380
executive is I'll actually Walk them through

00:30:55.380 --> 00:30:57.359
so let's say I was hiring like a I don't know

00:30:57.359 --> 00:31:00.220
a VP of something, right? I would actually walk

00:31:00.220 --> 00:31:02.700
them through something similar to like an investor

00:31:02.700 --> 00:31:05.500
deck, which is like here's a a deep dive into

00:31:05.500 --> 00:31:09.119
the company, the market or business model or

00:31:09.119 --> 00:31:13.000
biggest challenges. And I would, and I'd say,

00:31:13.079 --> 00:31:14.680
Hey, I'm going to walk you through it, but like,

00:31:14.839 --> 00:31:17.339
please like interrupt, ask questions anytime.

00:31:17.339 --> 00:31:19.420
I want you to get educated on the real estate

00:31:19.420 --> 00:31:22.160
of the company and our biggest problems and same

00:31:22.160 --> 00:31:24.619
thing. Like, do they interrupt with like really

00:31:24.619 --> 00:31:27.460
smart questions and comments? Because again,

00:31:27.480 --> 00:31:29.869
if we were collaborating in a real setting, I

00:31:29.869 --> 00:31:32.109
want to know what our conversation will be like.

00:31:32.170 --> 00:31:33.950
Are you going to jump in and actually dig into

00:31:33.950 --> 00:31:36.269
the details? Or are you just going to sit there

00:31:36.269 --> 00:31:39.170
for 10 minutes and have no commentary, no questions,

00:31:39.329 --> 00:31:42.890
nothing? And that's also correlated very well

00:31:42.890 --> 00:31:44.809
with performance. It's like, yeah, do they dig

00:31:44.809 --> 00:31:46.490
in right away? Do they have good feedback on

00:31:46.490 --> 00:31:51.109
this? Are they thinking about it? How do you

00:31:51.109 --> 00:31:54.309
screen? So say you've put out a job application

00:31:54.309 --> 00:31:58.049
or you've asked your friends to recommend people.

00:31:58.450 --> 00:32:01.230
How do you screen who to take forward from the

00:32:01.230 --> 00:32:04.589
very initial stage to interviews or these case

00:32:04.589 --> 00:32:08.569
studies you're doing with them? So for the first

00:32:08.569 --> 00:32:11.250
conversation, there's usually just some very

00:32:11.250 --> 00:32:13.609
basic screening criteria for that role. So that

00:32:13.609 --> 00:32:16.170
could be as simple as numbers of years of experience

00:32:16.170 --> 00:32:20.670
in a certain... uh for that specific uh skill

00:32:20.670 --> 00:32:22.309
set so like let's say it was sales it's like

00:32:22.309 --> 00:32:24.130
we might just say i'm making this out might be

00:32:24.130 --> 00:32:26.109
like oh you need five years of sales experience

00:32:26.109 --> 00:32:29.230
in healthcare tech or whatever it might be right

00:32:29.230 --> 00:32:32.670
so that's more basic um but i would say when

00:32:32.670 --> 00:32:35.410
we get to the actual conversation part of it

00:32:35.410 --> 00:32:37.890
is just like confirming details about like okay

00:32:37.890 --> 00:32:39.890
like when you say that you were doing sales like

00:32:39.890 --> 00:32:41.650
what does that actually mean like were you a

00:32:41.650 --> 00:32:43.930
bdr versus an account executive or something

00:32:43.930 --> 00:32:47.349
else But if after that first screening call,

00:32:47.890 --> 00:32:50.869
we're keen and they're still keen, then after

00:32:50.869 --> 00:32:52.430
that, we typically put them through what I call

00:32:52.430 --> 00:32:54.569
skills interview, which depending on the role,

00:32:54.650 --> 00:32:56.730
this could vary. But let's say for a client facing

00:32:56.730 --> 00:32:59.509
things like sales, customer success or something

00:32:59.509 --> 00:33:03.250
else, it's typically like a 60 minute, just a

00:33:03.250 --> 00:33:05.650
phone call where we'll ask them specific questions

00:33:05.650 --> 00:33:08.869
about competencies in that role. So for customer

00:33:08.869 --> 00:33:12.890
success, it might be like, hey, imagine you were

00:33:12.890 --> 00:33:18.119
implementing a customer here and you were running

00:33:18.119 --> 00:33:21.460
a kickoff meeting for implementing that customer,

00:33:21.940 --> 00:33:24.259
what would be your agenda for that meeting? So

00:33:24.259 --> 00:33:25.900
there'd be a number of questions to basically

00:33:25.900 --> 00:33:28.900
find out, okay, do they actually have the basic

00:33:28.900 --> 00:33:32.819
competencies for this role? And there's a number

00:33:32.819 --> 00:33:35.420
of different questions there. One of my biggest

00:33:35.420 --> 00:33:38.400
signals when doing those skills interviews is

00:33:38.400 --> 00:33:42.000
actually coming away thinking, okay, number one,

00:33:42.140 --> 00:33:43.839
yes, do they were they would answer the questions

00:33:43.839 --> 00:33:46.119
reasonably well, but two is, I've always found

00:33:46.119 --> 00:33:48.980
that our best hires, I would learn something

00:33:48.980 --> 00:33:50.599
from them in that skills interview, like they

00:33:50.599 --> 00:33:52.400
would give me an answer or say something where

00:33:52.400 --> 00:33:55.539
I'm like, Huh, I actually never thought about

00:33:55.539 --> 00:33:58.759
it that way. Or like, that's a really good idea.

00:33:59.039 --> 00:34:03.339
I never occurred to me to do it that way. So

00:34:03.339 --> 00:34:05.519
typically, if I'm learning something from the

00:34:05.519 --> 00:34:07.480
person, I'm like, Oh, that's a really good sign.

00:34:07.980 --> 00:34:10.079
if they pass that skills interview, then we take

00:34:10.079 --> 00:34:12.539
them to the actual like assignment that presentation

00:34:12.539 --> 00:34:15.579
or something else. And then from there, we put

00:34:15.579 --> 00:34:18.699
them through a final interview references. Now,

00:34:18.780 --> 00:34:21.820
some people actually don't like that. Some people

00:34:21.820 --> 00:34:24.940
say, wow, there's so many steps in the interview,

00:34:25.099 --> 00:34:26.920
or like, gosh, I have to do an assignment that

00:34:26.920 --> 00:34:29.519
seems like real work. And my answer is like,

00:34:29.579 --> 00:34:31.440
see, this is not for everyone. But what I tell

00:34:31.440 --> 00:34:33.500
people is like, look, like, yes, it's a rigorous

00:34:33.500 --> 00:34:36.630
process. What this means is that If you get through

00:34:36.630 --> 00:34:38.929
this and you actually want to work here, all

00:34:38.929 --> 00:34:40.949
your other colleagues here, you know they're

00:34:40.949 --> 00:34:43.429
really good because they all had to get through

00:34:43.429 --> 00:34:47.449
the gauntlet and they're working here now. So

00:34:47.449 --> 00:34:50.550
if you want to be working with really great talent,

00:34:51.369 --> 00:34:54.349
it takes work to filter people through that.

00:34:54.670 --> 00:34:56.769
But that's the opportunity here. And I think

00:34:56.769 --> 00:34:58.710
what you find is that most high -performing people

00:34:58.710 --> 00:35:00.170
are attracted to that. They're like, oh yeah,

00:35:00.250 --> 00:35:03.309
I want to work with A plus people who got through

00:35:03.309 --> 00:35:05.869
this process. Yeah, I'm cool with that. And a

00:35:05.869 --> 00:35:07.409
lot of people who do really well, they're like,

00:35:07.449 --> 00:35:09.429
oh, yeah, I actually enjoyed that assignment.

00:35:10.090 --> 00:35:12.090
I didn't find it to be an annoying thing. It

00:35:12.090 --> 00:35:14.989
was kind of fun to put this together or do a

00:35:14.989 --> 00:35:18.329
great job in all this. So I think it's just having

00:35:18.329 --> 00:35:20.929
clarity around, OK, what type of culture do you

00:35:20.929 --> 00:35:22.849
want to have? And what process do you need to

00:35:22.849 --> 00:35:24.309
build that? And the people who are attracted

00:35:24.309 --> 00:35:27.090
to that will self -select. And those who don't

00:35:27.090 --> 00:35:29.130
want to be part of that will self -select out.

00:35:29.130 --> 00:35:33.590
And that's totally fine. As you're growing seamless,

00:35:33.670 --> 00:35:35.750
how do you think about the decision to raise

00:35:35.750 --> 00:35:39.130
more rounds, give up more equity versus raising

00:35:39.130 --> 00:35:43.769
or getting a loan or getting venture debt? Yeah.

00:35:44.869 --> 00:35:46.809
Um, so, I mean, regardless of the instrument,

00:35:46.809 --> 00:35:49.289
like the question is, should I raise? And if

00:35:49.289 --> 00:35:52.150
so, how much and why? And I think the biggest

00:35:52.150 --> 00:35:54.030
mistake entrepreneurs make, which is the mistake,

00:35:54.150 --> 00:35:57.130
a mistake that I've definitely made too is, um,

00:35:57.130 --> 00:35:58.650
and it's gotten better now, of course, with the

00:35:58.650 --> 00:36:00.929
change in the markets, the last few years. But

00:36:00.929 --> 00:36:04.269
there was just almost like a momentum to just

00:36:04.269 --> 00:36:06.369
raise because you're supposed to and everyone

00:36:06.369 --> 00:36:09.389
else is. And the thinking I come around to as

00:36:09.389 --> 00:36:12.630
well, if I'm going to raise, I need to have a

00:36:12.630 --> 00:36:16.909
very clear idea that raising solves the problems

00:36:16.909 --> 00:36:19.730
that need to be solved because the reality is

00:36:19.730 --> 00:36:22.670
money does not solve every single problem possible.

00:36:22.989 --> 00:36:25.030
So a very common issue entrepreneurs run into

00:36:25.030 --> 00:36:29.880
is I need to grow faster. So I need to raise

00:36:29.880 --> 00:36:32.320
capital and hire a lot more sales and marketing,

00:36:32.320 --> 00:36:36.219
et cetera, people. But here's the reality. For

00:36:36.219 --> 00:36:38.860
some companies who don't have real product market

00:36:38.860 --> 00:36:42.039
fit yet, hiring more people does not solve product

00:36:42.039 --> 00:36:45.559
market fit issues, right? Like hiring salespeople

00:36:45.559 --> 00:36:48.360
does not create demand. Salespeople can convert

00:36:48.360 --> 00:36:51.800
demand into sales. But if you don't have enough

00:36:51.800 --> 00:36:53.840
demand for your product, enough leads coming

00:36:53.840 --> 00:36:56.630
into the company, like your salespeople would

00:36:56.630 --> 00:37:00.369
just be waiting for opportunities. And so I think

00:37:00.369 --> 00:37:02.289
what I found is, okay, are you crystal clear

00:37:02.289 --> 00:37:04.769
on the problems, the biggest problems you have

00:37:04.769 --> 00:37:07.389
to solve to grow? And does money solve that?

00:37:07.489 --> 00:37:09.730
Because if the answer is no, actually, I have

00:37:09.730 --> 00:37:12.869
to fix product market fit before I can invest

00:37:12.869 --> 00:37:16.530
in in growth, then fix that first. And the answer

00:37:16.530 --> 00:37:18.489
to that is probably not money. It's actually

00:37:18.489 --> 00:37:21.170
probably potentially becoming a smaller company.

00:37:21.699 --> 00:37:24.000
and figuring out why you don't have product market

00:37:24.000 --> 00:37:26.480
fit and getting that first. And I think there

00:37:26.480 --> 00:37:29.519
were a lot of companies who unfortunately thought

00:37:29.519 --> 00:37:31.880
money would solve product market fit problems

00:37:31.880 --> 00:37:34.800
and it does not. That's probably the biggest

00:37:34.800 --> 00:37:36.119
challenge, especially companies in healthcare

00:37:36.119 --> 00:37:39.619
face. When did you achieve product market fit

00:37:39.619 --> 00:37:43.699
and how did you know? Gosh, part of the challenge

00:37:43.699 --> 00:37:45.599
of product market fit is that it changes too,

00:37:45.659 --> 00:37:47.139
right? Like you could have product market fit

00:37:47.139 --> 00:37:50.210
with a specific subset of the market. and then

00:37:50.210 --> 00:37:52.150
reach a plateau and the need to refine product

00:37:52.150 --> 00:37:53.929
market fit. So it's almost like a never ending

00:37:53.929 --> 00:37:56.909
question because depending on the on the size

00:37:56.909 --> 00:37:59.369
of the state of the company, you can gain it,

00:37:59.369 --> 00:38:01.889
you can lose part of market fit. I would say

00:38:01.889 --> 00:38:05.550
probably the first time we had real product market

00:38:05.550 --> 00:38:08.250
fit, where, you know, if you listen to the original,

00:38:08.769 --> 00:38:10.670
like, like market, I think it was market recent

00:38:10.670 --> 00:38:14.980
description, which is like, you feel like Your

00:38:14.980 --> 00:38:17.380
product is just being pulled by the market like

00:38:17.380 --> 00:38:19.900
you're getting requests all the time Like it's

00:38:19.900 --> 00:38:22.760
hard to keep up with demand all that first time.

00:38:22.760 --> 00:38:24.739
We really felt something like that actually was

00:38:24.739 --> 00:38:29.199
probably around You know 2021 or so so this is

00:38:29.199 --> 00:38:32.079
like, you know eight nine years into the company

00:38:32.079 --> 00:38:34.539
I'm saying I didn't really feel like I had true

00:38:34.539 --> 00:38:37.039
part market fit. We had customers, right? But

00:38:37.039 --> 00:38:40.139
it was a grind and it was really only then when

00:38:40.139 --> 00:38:43.760
especially actually especially in in Canada where

00:38:43.880 --> 00:38:45.840
the government started investing more money in

00:38:45.840 --> 00:38:48.599
digital health and hospitals were being funded

00:38:48.599 --> 00:38:52.059
to procure solutions. So it's just like CMSMD

00:38:52.059 --> 00:38:54.460
that all of a sudden, people were just coming

00:38:54.460 --> 00:38:57.800
to us instead of us knocking on doors. That was

00:38:57.800 --> 00:39:00.019
the first time I felt real private market fit.

00:39:00.199 --> 00:39:02.199
And I was like, oh my gosh, it's so much easier

00:39:02.199 --> 00:39:05.639
when you don't have to convince someone so hard

00:39:05.639 --> 00:39:10.219
to buy this. But again, it could be gained and

00:39:10.219 --> 00:39:14.340
lost. It's not a one -time Oh, you passed go

00:39:14.340 --> 00:39:16.059
and your product market fit. Some of the biggest

00:39:16.059 --> 00:39:17.739
companies in the world have gained and lost part

00:39:17.739 --> 00:39:21.340
of market fit over and over. Yeah, I think there's

00:39:21.340 --> 00:39:24.960
lots of examples here. Kodak being a famous one.

00:39:27.059 --> 00:39:30.900
Talk to me about, you know, there's a philosophy

00:39:30.900 --> 00:39:34.559
that building a startup is an all in adventure,

00:39:35.420 --> 00:39:37.599
is there is no balance that exists in life when

00:39:37.599 --> 00:39:40.280
you're doing this. And this is kind of all encompassing.

00:39:40.579 --> 00:39:44.079
Do you share that philosophy? If not, how do

00:39:44.079 --> 00:39:47.260
you find balance in your life while being all

00:39:47.260 --> 00:39:53.079
in on seamless? Yeah, I think what I've come

00:39:53.079 --> 00:39:56.639
to realize is that the right answer is very personal.

00:39:56.900 --> 00:39:58.840
So for me, I don't believe in work -life balance,

00:39:58.880 --> 00:40:00.920
but I believe in work -life harmony. And I think

00:40:00.920 --> 00:40:03.539
probably a lot of startup founders do. And I

00:40:03.539 --> 00:40:07.079
think it's because a lot of founders get a lot

00:40:07.079 --> 00:40:10.800
of both purpose and energy from their startup

00:40:10.800 --> 00:40:14.420
and their work. And that's true for some people

00:40:14.420 --> 00:40:16.219
who are not even founders who just get a lot

00:40:16.219 --> 00:40:18.300
of energy and purpose from their work and careers.

00:40:18.300 --> 00:40:21.079
And there's others who get much less energy and

00:40:21.079 --> 00:40:23.480
purpose from their working careers and get that

00:40:23.480 --> 00:40:24.980
purpose from other places in life. And there's

00:40:24.980 --> 00:40:27.440
no right answer. But I think the right answer

00:40:27.440 --> 00:40:30.380
is very personal in terms of like figure out

00:40:30.380 --> 00:40:32.760
what's right for you. So for me, it's hard to

00:40:32.760 --> 00:40:36.039
separate the startup from like my identity and

00:40:36.039 --> 00:40:38.659
how I spend my time. And that's not me complaining

00:40:38.659 --> 00:40:40.699
because I get a lot of energy from working on

00:40:40.699 --> 00:40:43.420
our company. i don't expect everyone the company

00:40:43.420 --> 00:40:45.780
to get the same amount of energy and purpose

00:40:45.780 --> 00:40:47.940
so that they're spending as much time thinking

00:40:47.940 --> 00:40:50.820
or working on as me that wouldn't be a fair expectation

00:40:50.820 --> 00:40:55.920
um but but i'm not like upset about it i'm not

00:40:55.920 --> 00:40:57.739
complaining about how much time i spent on it

00:40:57.739 --> 00:41:00.559
because i actually enjoy and get purpose and

00:41:00.559 --> 00:41:03.320
energy and so it works for me and i think that's

00:41:03.320 --> 00:41:05.920
true for a lot of founders but i think that the

00:41:05.920 --> 00:41:08.239
disconnect is when founders don't understand

00:41:08.239 --> 00:41:12.429
why others don't feel the same way And when others

00:41:12.429 --> 00:41:16.250
who aren't founders don't understand why a founder

00:41:16.250 --> 00:41:18.190
or someone who like spend a lot of time working

00:41:18.190 --> 00:41:21.849
on stuff, like enjoys this sort of life, it's

00:41:21.849 --> 00:41:24.369
just everyone's different, right? We all exist

00:41:24.369 --> 00:41:28.130
on expect and a spectrum. So I think you just

00:41:28.130 --> 00:41:30.289
have to be honest with, okay, what gives you

00:41:30.289 --> 00:41:35.409
energy? And for me, it's this, right? We talked

00:41:35.409 --> 00:41:39.460
previously about. the customer driven path to

00:41:39.460 --> 00:41:42.559
building your offering when you first started.

00:41:43.079 --> 00:41:45.800
How do you think about that now, especially as

00:41:45.800 --> 00:41:49.179
you grow? I'm sure thoughts come like, well,

00:41:49.179 --> 00:41:52.400
I could build an EMR better than this. So how

00:41:52.400 --> 00:41:55.380
do you think about what the future holds and

00:41:55.380 --> 00:41:58.400
kind of staying within the brand you've built

00:41:58.400 --> 00:42:01.119
about reducing readmission rates versus branching

00:42:01.119 --> 00:42:03.940
out into other technical products that the hospital

00:42:03.940 --> 00:42:07.659
might need? Yeah, the really tough part about

00:42:07.659 --> 00:42:12.860
having existing company and product line is that

00:42:12.860 --> 00:42:17.300
it is very hard to just branch off and solve

00:42:17.300 --> 00:42:20.820
completely brand new, different problems. It

00:42:20.820 --> 00:42:25.480
is much easier to solve adjacent problems to

00:42:25.480 --> 00:42:30.380
your core product and problem space. And so for

00:42:30.380 --> 00:42:32.440
better or for worse, that's what we focus on.

00:42:33.260 --> 00:42:36.940
So, you know, we At least for now, we don't even

00:42:36.940 --> 00:42:39.099
think about the idea of, hey, could we build

00:42:39.099 --> 00:42:41.719
a completely new operating system for health

00:42:41.719 --> 00:42:46.179
systems? Because that would be too much of a

00:42:46.179 --> 00:42:48.539
brand new problem space than what we're solving

00:42:48.539 --> 00:42:50.820
today. But we do think a lot about adjacent things.

00:42:51.019 --> 00:42:54.400
So for example, right now, we focus a lot on

00:42:54.400 --> 00:42:56.940
patient care journeys going through a surgery,

00:42:57.380 --> 00:42:59.920
a cancer journey, or something else. But it's

00:42:59.920 --> 00:43:02.019
not hard to imagine that we could branch into

00:43:02.320 --> 00:43:06.599
other non clinical patient facing interaction.

00:43:06.599 --> 00:43:10.219
So at some point, maybe we do get it more into,

00:43:10.980 --> 00:43:15.920
you know, appointment scheduling, payments, or

00:43:15.920 --> 00:43:18.579
just anything, any digital interaction with the

00:43:18.579 --> 00:43:21.280
patient clinical or not, maybe we get into at

00:43:21.280 --> 00:43:25.159
some point. And there's other adjacent things

00:43:25.159 --> 00:43:28.699
that we can explore. But I think for us, given

00:43:28.699 --> 00:43:30.599
our size and stage, we're thinking a lot about,

00:43:30.800 --> 00:43:32.940
OK, how do we stepwise build out from the core

00:43:32.940 --> 00:43:37.260
right now? But that's a tough thing, right? Unless

00:43:37.260 --> 00:43:40.440
you're a huge company, it is very hard to make

00:43:40.440 --> 00:43:43.719
bets that are not adjacent to what your focus

00:43:43.719 --> 00:43:45.179
here is. You just don't have the bandwidth to

00:43:45.179 --> 00:43:50.579
do it. A question some investors ask founders,

00:43:50.719 --> 00:43:54.139
which I think is a lazy question, is What if

00:43:54.139 --> 00:43:57.360
Google did this? Or what if for our industry,

00:43:57.480 --> 00:43:59.719
you know, what if Epic did this or Cerner or

00:43:59.719 --> 00:44:03.159
Oracle? No. What do you think of that question?

00:44:03.159 --> 00:44:05.860
And how how did you answer that question when

00:44:05.860 --> 00:44:09.159
it was posed to you? It was funny because that

00:44:09.159 --> 00:44:11.280
that's the alleged reason that we got rejected

00:44:11.280 --> 00:44:14.059
by it, by YC app, our interview, like, you know,

00:44:14.079 --> 00:44:16.800
almost 10 years ago, they, you know, we had this

00:44:16.800 --> 00:44:18.559
interview and then we got an email saying, hey,

00:44:18.699 --> 00:44:20.980
sorry, sorry, we didn't accept you. We think

00:44:20.980 --> 00:44:22.980
the EMR is going to build this. And I was like,

00:44:23.210 --> 00:44:26.030
That seems like a very non YC thing to say, because

00:44:26.030 --> 00:44:28.309
YC's whole thing is that like, it's a lazy question

00:44:28.309 --> 00:44:30.030
to ask, you know, why won't the incumbent do

00:44:30.030 --> 00:44:33.710
this? So I thought that was kind of funny. But

00:44:33.710 --> 00:44:36.510
but I think the reality is like, look, the incumbent,

00:44:36.989 --> 00:44:39.849
whether it's an EMR, someone else may very well

00:44:39.849 --> 00:44:42.309
try to build this, they may have some they may

00:44:42.309 --> 00:44:44.010
or may not they may have, but they may have an

00:44:44.010 --> 00:44:47.369
overlapping product or plan to. But that's true,

00:44:47.449 --> 00:44:49.070
whether in healthcare or not. And the reality

00:44:49.070 --> 00:44:51.329
is, and I always tell people the same thing,

00:44:51.389 --> 00:44:54.360
it sounds easy, but it's hard. It's, is your

00:44:54.360 --> 00:44:58.079
product going to solve it 10 times better than

00:44:58.079 --> 00:45:01.039
the incumbent on a dimension that actually matters

00:45:01.039 --> 00:45:03.360
to the customer? And that might, and that can

00:45:03.360 --> 00:45:05.860
be anything that could be the customer wants

00:45:05.860 --> 00:45:08.920
this product implemented 10 times faster, or

00:45:08.920 --> 00:45:10.980
they want 10 times better support, or they want

00:45:10.980 --> 00:45:13.840
it 10 times cheaper, or some combination of the

00:45:13.840 --> 00:45:17.500
above. But if you can figure that out, and focus

00:45:17.500 --> 00:45:19.800
on that, You could beat the incumbent largely

00:45:19.800 --> 00:45:23.019
because the incumbent has so many other things

00:45:23.019 --> 00:45:25.380
to care about, right? Like you can take a big

00:45:25.380 --> 00:45:28.820
EMR who has so many other core products. Unless

00:45:28.820 --> 00:45:32.099
you're competing to displace the EMR, it's very

00:45:32.099 --> 00:45:35.340
hard for them to focus and do your product well.

00:45:35.820 --> 00:45:38.440
Where startups fail is that they focus on a product

00:45:38.440 --> 00:45:41.719
that's a nice to have for the customer. And if

00:45:41.719 --> 00:45:44.119
it's a nice to have, then the customer has no

00:45:44.119 --> 00:45:47.280
urgency to pick. the product that will get to

00:45:47.280 --> 00:45:49.920
market the fastest or deliver the best value,

00:45:50.199 --> 00:45:52.260
whereas the highest performing, because if it's

00:45:52.260 --> 00:45:54.820
just a nice to have, they are happy to wait for

00:45:54.820 --> 00:45:57.460
the incumbent to maybe at some point deliver

00:45:57.460 --> 00:45:59.980
that same product that could be 10 times worse.

00:46:01.039 --> 00:46:04.719
But if it's a nice to have, there's just no urgency

00:46:04.719 --> 00:46:07.519
to buy anyone's product, let alone the startups.

00:46:09.380 --> 00:46:11.079
And that happens because in healthcare, there

00:46:11.079 --> 00:46:15.139
are just a lot of products that can help patients

00:46:15.139 --> 00:46:17.840
and care teams, which is why we want to build

00:46:17.840 --> 00:46:20.800
them as entrepreneurs and innovators, but just

00:46:20.800 --> 00:46:24.400
may not be important enough of a problem that

00:46:24.400 --> 00:46:26.639
a health system will pay money for tomorrow.

00:46:27.320 --> 00:46:30.039
And that's the disconnect. That's the weird thing

00:46:30.039 --> 00:46:32.119
in healthcare. In any other industry, the startup

00:46:32.119 --> 00:46:33.679
will say, okay, I'm going to pivot to a brand

00:46:33.679 --> 00:46:35.739
new problem that actually will make money. In

00:46:35.739 --> 00:46:37.719
healthcare, you're like, no, no, no, like, I

00:46:37.719 --> 00:46:39.900
really want to solve this problem that is so

00:46:39.900 --> 00:46:42.489
important for patients. You wouldn't get that

00:46:42.489 --> 00:46:45.269
in accounting. The entrepreneur would say, no,

00:46:45.269 --> 00:46:47.190
I'll just move on to construction or some other

00:46:47.190 --> 00:46:49.730
accounting problem. You know what I mean? Yeah.

00:46:50.389 --> 00:46:53.409
If you had to build a direct to consumer product,

00:46:53.449 --> 00:47:01.030
what would you build? Oh my gosh. I actually

00:47:01.030 --> 00:47:03.369
would have to think about that because I don't

00:47:03.369 --> 00:47:05.150
spend that much time thinking about the consumer

00:47:05.150 --> 00:47:11.230
space. That's a good question. I mean, to be

00:47:11.230 --> 00:47:14.010
honest, it would probably be something that is

00:47:14.010 --> 00:47:16.869
very, very disconnected from the traditional

00:47:16.869 --> 00:47:21.010
health care system, because I generally believe

00:47:21.010 --> 00:47:24.929
that clinicians do questions things well, and

00:47:24.929 --> 00:47:28.329
the right consumer product that, you know, doesn't

00:47:28.329 --> 00:47:30.469
impact the clinician patient relationship or

00:47:30.469 --> 00:47:35.750
the other consumer products that will win. But

00:47:35.750 --> 00:47:40.110
I have to think about that one. Yeah. If you

00:47:40.110 --> 00:47:43.329
do raise a next round, a common question from

00:47:43.329 --> 00:47:46.630
VCs would be around how are you using the latest

00:47:46.630 --> 00:47:53.150
AI? And how do you think about that? What are

00:47:53.150 --> 00:47:56.349
your thoughts on AI agents and their place in

00:47:56.349 --> 00:47:59.349
healthcare? And are you thinking about leveraging

00:47:59.349 --> 00:48:04.570
them? And if not, why not? Yeah, I mean, I'm

00:48:04.570 --> 00:48:10.400
a big believer that any tech AI or not is just

00:48:10.400 --> 00:48:14.659
a tool to solve a problem. So investors might

00:48:14.659 --> 00:48:17.460
not like that, but I would try to figure out

00:48:17.460 --> 00:48:19.820
what's the problem I'm going to solve and the

00:48:19.820 --> 00:48:21.599
best solution to that, which may or may not involve

00:48:21.599 --> 00:48:26.159
AI or agents or any other things. I do think,

00:48:26.159 --> 00:48:31.719
and I agree that I think AI opens up the opportunities

00:48:31.719 --> 00:48:34.320
for what solutions are possible and that accelerates

00:48:34.320 --> 00:48:38.300
a lot of things. I think that could very well

00:48:38.300 --> 00:48:40.380
be part of the pitch because it would open up

00:48:40.380 --> 00:48:42.599
some opportunities and accelerate things that

00:48:42.599 --> 00:48:44.239
make it a much more attractive startup. I think

00:48:44.239 --> 00:48:46.599
that's very, very true. And I would probably

00:48:46.599 --> 00:48:50.880
look for a way to apply AI, but I wouldn't say

00:48:50.880 --> 00:48:53.360
for me it would be necessary to use AI to build

00:48:53.360 --> 00:48:54.940
a new startup. Although I think it would be very

00:48:54.940 --> 00:48:58.599
likely that we would. I would say for us though,

00:48:58.639 --> 00:49:01.340
what's interesting is that the lowest hanging,

00:49:01.380 --> 00:49:04.530
most common use cases for AI in healthcare right

00:49:04.530 --> 00:49:07.210
now, as you know, are less clinical, more back

00:49:07.210 --> 00:49:09.429
office administrative things that pose less of

00:49:09.429 --> 00:49:12.190
a safety concern, that get more easily approved,

00:49:12.230 --> 00:49:15.050
et cetera. And so because Seamless is very much

00:49:15.050 --> 00:49:20.889
in the clinical patient journey space, our customers

00:49:20.889 --> 00:49:26.190
so far have not been enticed by applying AI to

00:49:26.190 --> 00:49:28.809
the patient interaction. And so no one's really

00:49:28.809 --> 00:49:31.210
saying, hey, Seamless, we really want you to

00:49:31.210 --> 00:49:33.929
have you know, agents to guide patients through

00:49:33.929 --> 00:49:36.329
these journeys instead of, you know, using mobile

00:49:36.329 --> 00:49:39.190
and web today. Now, I do think long term what's

00:49:39.190 --> 00:49:41.349
going to happen is like there will be some patients

00:49:41.349 --> 00:49:44.250
who don't like agentic experiences who actually

00:49:44.250 --> 00:49:46.190
prefer the curved version of seamless. And that's

00:49:46.190 --> 00:49:48.750
the best way to engage. But there will be some

00:49:48.750 --> 00:49:51.110
and maybe it will be a growing percentage of

00:49:51.110 --> 00:49:53.550
the population who eventually will want agentic

00:49:53.550 --> 00:49:56.170
experiences. And we will have to build agents

00:49:56.170 --> 00:49:58.230
to guide patients through, let's say, a surgery.

00:49:58.920 --> 00:50:02.019
But I don't think it's going to likely be agents

00:50:02.019 --> 00:50:06.079
only ever, or at least not for a very long time.

00:50:06.500 --> 00:50:08.099
And so the question is, well, when's the right

00:50:08.099 --> 00:50:10.039
time then to introduce things like agents? And

00:50:10.039 --> 00:50:13.059
I think for us, most likely it will be a stepwise

00:50:13.059 --> 00:50:15.300
path to getting there, not because we could not

00:50:15.300 --> 00:50:17.960
just go and build agents, but because I think

00:50:17.960 --> 00:50:20.420
we want to match the urgency of the market. So

00:50:20.420 --> 00:50:22.320
building a bunch of agents now that customers

00:50:22.320 --> 00:50:25.039
won't use is kind of pointless to me. So I think

00:50:25.039 --> 00:50:28.099
we see some middle ground. So for example, In

00:50:28.099 --> 00:50:31.960
our product, we have all these clinical pathways

00:50:31.960 --> 00:50:34.679
and content that have been vetted by the customer

00:50:34.679 --> 00:50:37.300
and configured by the customer, let's say, for

00:50:37.300 --> 00:50:39.599
heart surgery. And I could see a world where

00:50:39.599 --> 00:50:42.579
we embed a conversational interface, like a chat

00:50:42.579 --> 00:50:47.840
bot, into the product where it's using retrieval

00:50:47.840 --> 00:50:50.280
augmented generation. It's basically trained

00:50:50.280 --> 00:50:53.800
only on the customer's pathways and clinical

00:50:53.800 --> 00:50:56.940
content and can answer questions about that.

00:50:56.889 --> 00:50:59.610
with, you know, minimization of hallucinations.

00:50:59.610 --> 00:51:01.110
So I could see something where it's like, okay,

00:51:01.150 --> 00:51:04.489
it's not totally like agentic at all. It's just

00:51:04.489 --> 00:51:07.909
like a, you know, like almost like a, a custom

00:51:07.909 --> 00:51:10.949
GPT, if you will, trained on the customer's content

00:51:10.949 --> 00:51:13.309
that can answer the most common questions, but

00:51:13.309 --> 00:51:15.429
in a way that clinicians will feel comfortable

00:51:15.429 --> 00:51:18.150
because it's like, Hey, it's only going to produce

00:51:18.150 --> 00:51:21.829
content that you have vetted that specific to

00:51:21.829 --> 00:51:24.389
your, your care team and institution, but still

00:51:24.389 --> 00:51:27.320
has that like, AI sort of chatbot experience

00:51:27.320 --> 00:51:29.719
that's kind of cool that you want to do. So I

00:51:29.719 --> 00:51:32.099
feel like there may be a stepwise function between

00:51:32.099 --> 00:51:35.500
what we do now and actual agentic experiences.

00:51:35.920 --> 00:51:37.400
We're still trying to figure out the timing of

00:51:37.400 --> 00:51:40.320
that and the right way to do it. But that's why

00:51:40.320 --> 00:51:42.219
I feel is like probably for us the best way to

00:51:42.219 --> 00:51:46.920
do it. Thanks so much for sharing everything,

00:51:47.159 --> 00:51:49.139
if I'm being frank. And I think founders will

00:51:49.139 --> 00:51:51.639
learn a lot from this. Any last piece of advice

00:51:51.639 --> 00:51:55.670
for founders building in healthcare? No, just

00:51:55.670 --> 00:51:58.130
don't do it. And if that doesn't stop you, you're

00:51:58.130 --> 00:52:00.590
meant to do it. Awesome. Thanks, Josh.