Surfer --> P&L owner
The path to being a top operator can be a winding one. It’s hard to chart a direct course to the top of the org chart! Because of that, we’re starting a series of interviews focused on the careers of people who have landed in the c-suite, run P&Ls, or are just badass operators of various stripes. Our first interview is with Sam Toole, who just left a GM role at Nomad Health to become an investor at Primary Ventures.
Our goal with this series is simple: we want to shine a light on the underappreciated folks who actually get things done at startups and by doing so help you get closer to figuring out the career path that’ll lead to your ultimate goal, whether that’s being a founder, an operator, or an investor.
Don’t worry, we’ll also still be sending out top jobs at under-the-radar startups every week. If you want to get serious about the job search, though, you should check out onejob premium, where we send out 3 great jobs each week and give you back-door ways to apply.
From Surf to Sales: An Interview with Sam Toole
Before joining Primary Ventures, Sam worked his way up to be GM of the Physician Marketplace at Nomad Health, an online marketplace for healthcare jobs that has raised $50M from First Round, RRE, .406 Ventures, and more. In our interview Sam talks about how he set goals and motivated his team, his path to the GM role, his days as a surfer/entrepreneur on Nantucket, and his advice for young operators.
On being a General Manager at a high-growth startup
When I took on the GM role at Nomad, my two goals were to continue to grow our core business 20-25% each quarter and to help reimagine our physician staffing business line. Physician staffing was the original business that we launched, but due to the market dynamics, our travel nursing business was much easier to scale (more liquid supply, easier demand side acquisition). On the physician side, we knew that there was a functional business ($5B+ market), but what we needed to learn was whether there was a scalable business as well.
To solve this challenge, we started by going back through all of the data and re-evaluating our initial assumptions. We worked to answer, “What were we right about?” and, “What were we wrong about?” Early on, a lot of our work was internal calibration to help us figure out where we should focus. Once we had a baseline, we looked for different paths to explore. During this whole period, a key challenge for me was balancing exploring the paths, while still working to grow top line revenue.
On the experimentation process
It sounds super cheesy, but early on we spent a lot of time doing things that “don't scale” to validate or disprove our hypotheses. Depending on the initiative, we took a step back weekly or monthly and evaluated both our targets in the core business and whether we had made progress on the initiatives that we were testing. We focused on trying to eliminate potential paths as quickly as possible so that we could focus on the things that actually worked.
One of the paths we explored very deeply was partnering with staffing agencies. To do this, we spoke to 20+ staffing businesses and set up pilots by leveraging Google Sheets and our existing product. Ultimately though, we figured out that it wasn't the right approach and crossed it off the list because it was too far afield from our other business line.
Hindsight being 20/20, we probably spent too much time on the theoretical and didn't cross things off the list as quickly as we should've. For example, we considered going out and buying physician staffing groups and creating a technology layer over them. Really fun exercise to think about, but given the capital we would need to raise it wasn’t realistic.
On top of this, a big chunk of the team's focus was on supporting and converting existing revenue, rather than figuring out the new, scalable strategy. It ended up being okay, but there's a world where we could've gotten to a similar spot by being more focused early.
Wait a second - how did Sam become a GM in the first place?
Well, I was born and raised on Nantucket. When I was in high school, I landscaped and gave surf lessons. After my first year of college, I decided that surfing was more fun (and better money) than mowing lawns, and decided to focus on that. Five summers later, we had 10 instructors doing 100s of lessons per summer at $70 per lesson per person. We sold t-shirts on the side, as well.
Being honest, that was the probably the best job I’ll ever have! When I wasn't teaching I was surfing and hanging out with all my friends on the beach. Along the way, I also got my first sales experience (going up to strangers on the beach and convincing them to let me take their children surfing) and my first experience as a manager.
Sam’s surf school, source: medium.com/@samtoole/from-surfing-to-software-83b8cccb238c
On the fun parts of the entrepreneurial journey...
Eventually, we started to design t-shirts that we'd give away with the surf lessons. Nantucket has a bunch of college students that come and hang out over the summer, so we'd stuff backpacks full of t-shirts and sell them for $20 at beach parties. I connected with a media entrepreneur and convinced him to help me spin out a separate e-commerce brand.
So, I spent my senior year of college figuring out how to design and manufacture clothes. We launched and managed to sell about $300k of clothes in 9 months and found 20 college ambassadors to create content for us as a way to stay relevant during the winter.
...and the hard parts
But, ultimately, my friend and I weren't on the same page for the business, which was incredibly hard at the time. We sold the business back to one of our original investors. After that I wasn’t sure what I wanted to do, and worked for 6 months at a small PE shop and acquired some small revenue-cycle management companies. I figured out that it wasn't super fun cold calling small businesses owners in Michigan and trying to convince them to sell to us.
During that time, I started to become interested in venture capital when I reconnected with a Hamilton college alum who was running a software agency. I ended up joining the company and over 2 years, I was the only salesperson and helped grow the business by 5x. The team went from 30 people to 120 which was an awesome experience. We sold custom software development, so I ran a very consultative sales process and got to learn a lot about the technical side of things and about managing stakeholders.
On how he found Nomad and went from individual contributor to executive in <18 months
I got connected to Nomad through .406 Ventures and joined as their first sales and BD person, employee #6. I started out carrying a bag: actually going out and selling. But I was ambitious so I said: I'll just keep doing more. First, I took on sales ops and sales enablement. Then, I built the sales team and became head of sales. I ended up managing a team of 10: BDRs, account execs, account managers. I did that for a year before my role shifted to the GM side.
His biggest learning from being a GM
You're a coach, not a player.
On his transition to VC
I've been on the VC side for a few weeks now, and I've figured out that I can do it pretty well remotely! To say the very least, it’s certainly an interesting time to join. To date, my operating background has been helpful: I'm using my BD/sales/go-to-market experience to inform my conversations with companies and I'm trying to focus on where I can actually add value. For example, I spoke with a founder of a healthcare marketplace today and my background allows me to understand the drivers of their business pretty quickly.
I've only been a VC for a month, so there are lots of areas where I don't know things or don't have the answer. Given Primary’s focus and stage, I believe in Benchmark's "see the present clearly" mindset, but have also quickly learned how hard it is to actually live by that! So, I’m trying to read a lot and keep an open mindset about markets and business models.
On what he'd be doing if he was running a P&L at a healthcare startup experiencing a surge in demand from Covid-19
I'd view it first and foremost from the patient's perspective: what can we do today to have a meaningful impact on patients and providers? For most healthcare companies that ends up aligning with activities that drive revenue.
For example, if you're at a telemed company and you can acquire more doctors, that enables you to serve more patients, which drives more revenue for you. You do everything under the sun to patch things together to make that happen, even if it's not perfect. Maybe you structure a deal differently to get it done quickly, even if it means that the terms are less favorable. People at health startups tend to be impact-driven, and this is the time to lean in to that.
The best piece of advice that he's received
Perception is reality. This can be particularly true on the sales side, especially at the earliest stages.
Frameworks for managing people
I tend to believe that people are driven by a couple of core incentives. Figure out what those incentives are for each person and make sure what you're asking people to do aligns with those incentives. In general, I think a lot about understanding incentives because it helps understand people.
His advice for young operators
If you're managing people: they're humans. You have to manage everyone differently. Different things will motivate different people - you can't just set up a structure and expect it to apply to everyone. You really need to get to know people and figure out what's important to them. Also, even if you think it’s cheesy, remember that the small things matter!
How to connect with Sam
I’m easy to find on Linkedin. I’m also “bad” at Twitter, but working to improve! It will likely be a bunch of things that I read and if that’s interesting to you, I’m @Samdtoole.
Liked this interview? Share it with a friend!