1) Hello Joe, before we begin this interview, thank you for joining us today. How are you doing?

Hello there!  Oh you know, just making like a duck: composed for this interview, but ugly paddling underneath to keep moving forward.

2) So, you have worked in quite a few leadership roles during your career. What role specifically has been the most teaching part of your career and how?

Every year as a CEO seems to feature big lessons, but I would say the most defining one for me is actually from my last startup, a healthcare project closest to home.

That was when I learned just how wrong my ideas, both about the product and myself, were.  I learned about the importance of not thinking just because you are the customer, you know what the customer wants.  I learned about the importance of rigorous testing to find out what they want.  I learned about the fine line between pivoting and losing your way into feature creep.  I learned about the importance of focusing on personal compatibility more than the skillset of a technical leadership hire.

It was like 10 years of lessons in 2.  Overall, all these lessons led me to our value system with Topflight, and to our current decision-making about products and people.

3) As designing the user experience has been a prominent part of your career as well, do you have any tips to share that can be helpful for UI/UX designers from various industries?

I’m sure my design leadership Helena & Joshia could give you way better tactical tips, but here’s my personal take.  Kind of related to what I was saying above, design for us is also about calmness.  We have to calmly balance the end user’s needs, the business’s needs, our experience, and a designer’s natural desire to create something that’s never been created before, and these can be conflicting motivations.  What’s been most helpful for us, is treating our north star as data.  We run our design prototypes through end users, and their quantitative and qualitative response to the prototype serves as the final word on a successful design, no matter how we personally feel about it.  

We see the job of a designer as somewhat different than many companies might. It’s to de-risk development by validating what we’re building before we build it.  That’s it.

4) The tech world is evolving super fast; for aspiring entrepreneurs and industry leaders out there, what technologies would you recommend might have a great future?

I think chasing after new technologies is actually dangerous.  If you’re always just trying to keep up with new tech, that to-learn list is infinite and expanding.  It’s like an upside-down mountain you need to climb.  

Instead, think of new tech as just a right-side-up mountain, where the top of the mountain is the goal, and steps are the technologies that will get you there.  Yes, you’ll still be learning new things all the time, but everything you learn will have a clear purpose.  It’s more likely to energize you because, with each layer, the end goal is closer in sight.  

Now, I do scour the landscape for the latest tech - you can’t ignore new tech as a tech company - but we only add it to our R&D queue when we feel there’s something that would accelerate our company mission.  Then we lean-test it for product-market fit.  Recent examples are ML experiments & blockchain for healthcare and no-code for healthcare.  This way it feels like all we’re doing is staying in our lane, competing with no one else besides ourselves.

5) How has your experience been being a lead at Topflight health?

It’s just coming full circle.  I’ve never left healthcare, but while I started out being 100% in it, with Topflight I had to play a broader operational role for many years.  We now have super competent leadership running our ops and product departments, so I am extremely privileged to be able to get back to my healthcare roots.  

With Topflight Health, I get to work with more healthcare startups and investors about their fundraising and go-to-market strategy, so I have a lot more ownership over where our healthcare companies go as part of our portfolio.  This couldn’t be more daunting of responsibility, or exciting, depending on how much caffeine I’ve had that day. 

6) Where do you plan to take the company in the future and what markets are you planning to explore?

In 2 years, my goal is to enable 100 startups per year to find traction with amazing ideas, instead of the 20 or 30 per year that we’re helping now.  To get there, we know it will take a combination of new technology, lowering time to market, especially on custom code, and a sophisticated fundraising arm.  Because the two things standing in the way of this goal are not enough runway and not enough holistic skills and experience to avoid common startup traps.  We believe we can solve both if we stick with the plan.    

In 2 years, we also are expecting to make a much bigger play for enterprise healthcare.  As we move more into the enterprise, we’ll lean on our R&D in creating robust DevOps, compliance, and governance.  For enterprise companies, we see ourselves as the best way to pilot and validate new innovations without the speed and cost disadvantages of an enterprise.  

Market-wise, we expect to continue our growth in healthcare, fintech, and web3 markets.  Although web3 (crypto) is in a bear market, we have no doubt that decentralized protocols are the future, and at some point, they’ll touch every industry.  We all know traditional finance and hospitals (in particular) are very resistant to change, but we still want the first-mover advantage. 

7) To grow your company, what market tactics have been very successful?

A lot of testing, alongside hiring experts selectively who know how to dominate a channel.  We’ve never been afraid of testing literally anything. 

We’ve hustled on Upwork proposals and RFPs in the early years.  We wrote to founders from databases and tested different messaging.  We tested paid ads of all types, image, video, short-form, long-form, animated product videos, and speaking videos - on Facebook, YouTube, and Google ads.  We religiously measured our customer acquisition cost, gave everything at least a $1000 budget, and dumped it once the target CAC was lost.  

Inbound has been the big winner for us, as I mentioned before, under Charudhi and her team.  But even then, we’re still doing research-test-measure cycles on a biweekly basis.  The grind truly never stops, even after you find something that works. 

That’s the first part. 

Sales is the second.  Bringing in the right closers has been HUGE.  Nothing annoys us more than sales types, so we won’t tolerate that coming from us either.  On sales calls, we try to add value and guide people toward making the right decision.  If we end up being on the tail end of their decision, great.  If not, we’ve helped someone.  Our salespeople work hand in hand with the product team to evolve our product offerings, which is another differentiator in our process: sales owning the product, not just selling it. 

Of course, time is money too, we have to prioritize whom we meet with - that’s where adding a prequalification process for our ICP (ideal client profile), before we get on a call, has saved us from taking 30 extra monthly meetings that likely would not convert into long-term partners.

TLDR: We don’t treat marketing and sales as something that’s not less technical than product or code.  We put it on a pedestal as the growth engine of any company.  Every product innovation we’ve been able to reinvest into is thanks to the sales gods, so we never forget to pay our respects.

8) Would you like to share some numbers that reflect the fast growth of Topflight health?

We are not able to disclose that here, but I can disclose we’ve grown revenue by about 500% over the last 3 years and made the Inc5000 in 2022 for fastest-growing companies and ranked 171 among software companies.

9) Can you take us through the work culture that is applied throughout Topflight Health?

The work culture is probably what I’m actually proudest of because we’ve never really lost sight of that even when so much has changed on the exterior.  We’re biggest on radical transparency, accountability, speed, and flexibility.  

Radical transparency means regardless of role if you see something wrong with either a person’s performance or product, you’re expected to speak up and be the change.  

Accountability simply means you do what you say you’re going to do.  It’s super basic, but missing from so many companies.  It shouldn’t be unusual, but alas.  

Speed because it’s in our startup DNA.  We don’t have a year to find out if something will take.  We have weeks or months, just like our clients.  Eat your own dog food.  

Flexibility because we’re human.  We encourage people to have lives outside of work, liberally travel and take weekends completely off.  As we build healthcare products, it would be hypocritical to not prioritize our health!  

I actually believe the balance of intensely passionate “go time” with the flexibility to recharge as needed, has led to much better product solutions than we ever could’ve created otherwise.

10) How does the company handle its day-to-day operations? Do you mind taking us on a journey between order placement and the delivery of your services?

Run by our COO Bajer, everything is automated right now, either completely by a tool like Hubspot, Zapier, ClickUp, or by sending a request for a specific action to our ops team, which has an SOP to continue the automation chain once a response happens to that action.  We believe heavily in automating whatever you can without jeopardizing quality, including most repetitive communications.  

We want to spend as much of our manhours (especially the expensive talent) as possible being creative and delivering solutions, so over the years, we’ve designed ops to run with minimal intervention, as a set of if-then statements.

11) Before we wind up this blog, we would love to know some of the most amazing achievements of your career.

This one is really hard to answer.  For one, I don’t think any of my said achievements are mine alone.  I’ve had tremendous help every step of the way.  There is a village behind every “successful” CEO.

But if you’re going to corner me, I would say my biggest personal achievement is just persisting.  To have not quit after the insane growing pains, including very talented people leaving the company, or facing legal issues that drained me.  Just ask my wife how many times I thought of giving up.  So, doggedly chasing growth 6 years later.  I would say that’s my biggest achievement, and the same probably goes for any company that survives the test of time.

The milestone however that I’m proudest of, is building an incredible team.

A bit of backstory here: I started Topflight as a solo founder, because of past cofounder drama.  I wanted to play it safe this time.

That did get us pretty far, but 1 to 2 years ago, it also started holding us back.  I had to learn to trust people who hold the most sway over the company, to make decisions.  That’s been a huge internal tug of war, one that I still deal with on a daily basis, but by letting go more and more, we’ve been able to move from what felt like a run-by-a-single-person company, to a dynamic management team where multiple people can have a strong point of view, see it to the end, and own that decision.  It’s created an entrepreneur-in-residence culture, one that I always dreamt of but didn’t think we could afford it.  Well, turns out we could afford it, because these people are much smarter than me.

Just as one notable example, the Topflight Fund would not exist today, if it were just me calling the shots.

With the team we have today, we’re already poised to scale beyond me.  Like a proud parent is proudest when the kid flies the coop, when I’m no longer needed to grow the company, that’s the most amazing achievement I can imagine.

Ironically, for any insecure CEO out there like me, with the freedom to breathe and think, I’ve been able to give more creativity and intention toward the company than ever, and now I can’t see myself leaving.  It truly has only helped me give more of myself.