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Featured Founder: Will Sitton of SlipSeat

Welcome to our Featured Founder series, where you’ll meet startup founders from Tampa-St. Petersburg who are building and scaling their ventures to solve some of the world’s greatest challenges. We interviewed Will Sitton of SlipSeat, which supplies truck drivers and owner-operators to motor carriers using a freelance marketplace.

What were you doing previously and what inspired you to launch your company?

I come from an industry so small that searching Wikipedia for it in quotes will return 0 results.  It’s called driver leasing, and it deals with 3rd party truck drivers.

While it is largely unglamorous, back-office type work, driver leasing companies are experts in the unique rules and regulations regarding 3rd party truck drivers.  Most operate as specialized DOT temp agencies.

My employer used driver leasing as a tool in providing customized 3rd party trucking solutions for clients.  Companies would outsource their complex trucking operations to us, and we used driver leasing to provide the services.  We specialized in mission-critical, hyper-seasonal, and/or mass movements, especially those that required a significant amount of operational precision.  I ran sales and operations.

One night, I couldn’t sleep, and while staring at the ceiling, I started thinking about the growing driver shortage.  It was becoming an industry hot topic, and earlier that day I had heard a radio spot on it and that evening had read yet another article about it.  Two things dawned on me: 1) everybody was looking at the wrong root cause and 2) the shortage could be “solved” without adding drivers.

What most people don’t realize is that the capacity already exists – it just isn’t being used properly.  Half of all truck drivers have at least one available day that they could be driving but don’t.  It could be they don’t want to work or that they can’t find a truck driving job for 1 or 2 days per week because it’s not cost-effective for the trucking company.  There are also millions of workable hours lost in the “system” – hidden, untapped capacity tied up in processes.  If just a small portion of the total unused capacity could be turned into a useable supply, it would offset the shortage.

Although I had fleshed out the concept and knew it was solid - I had used similar math and logic before in a few mass movement projects - I still resisted joining the startup world.  It was my Dad who finally convinced me to launch SlipSeat.  If it wasn’t for him (and the rest of my family and friends), we never would have made it this far.  (Thanks everyone!)

What pain point is your company solving? What gets you excited to go to work every day?

Since we are a marketplace, we have two different sets of relevant pain points to resolve – one for demand and one for supply.

The truck driver labor market has been in shambles for years; COVID has only made it worse.  Although driver absenteeism and turnover are both high, the #1 problem for the trucking companies is a large, growing shortage of truck drivers.  SlipSeat was created to solve it by pooling unused capacity from existing and returning drivers and dispensing it to trucking companies using the tenets of driver leasing and driver sharing; however, operationally, we’re a solution to all three – the shortage, turnover, and absenteeism.

Because we solve multiple big operational problems, our customers can streamline their operations and lower their operating costs.  Overall, trucking companies save money, time, pain, and worry and improve their cash flow, but where we have sufficient driver density, we can be an absolute game-changer for trucking operations that do shift-type work, especially those in Intrastate trucking (about 40% of the industry).

On the supply side, our goal is to be the last “job” a driver ever has.  The shortage will be around for the next 20 or so years.  We strived to create the ideal driving environment so drivers would keep adding supply year after year.  We effectively solve 8 of the top 10 driver pain points, including the #1 which is more money.

(If anyone has questions about how we do things or the benefits we provide, feel free to email me at  I’d be happy to explain.)

I’m an efficiency geek who loves big trucks, solving problems, and helping others. Running a startup that maximizes trucking efficiency while making both sides of the equation better off is arguably my dream job! (Thanks Dad!)

Name the biggest challenge you faced in the process of launching the company. How did you overcome it?

Our biggest challenge to date has probably been developing an effective chicken/egg strategy that’s bootstrap friendly. Commonsense in a supply-constrained market would be to add drivers first and then trucking companies, but driver screening is costly, and there is a timing component to putting a driver in a truck for the first time. A driver-first approach isn’t necessarily ideal. It would be better to bring drivers and trucking companies on at the same time, but that would take people and necessitate funding, which we don’t want to do just yet.

Conceptually, our platform is designed to create a large pool of shared, on-demand truck drivers, but it works on a small scale too if driver density is high enough.  So, instead of first finding drivers to sell on our marketplace, we’re targeting a subset of larger trucking operations, which utilize multiple trucking companies, where the overall operation can gain efficiencies when the trucking companies aggregate their drivers into a pool.  The best part is that the more trucking companies that join, the better off everyone becomes.

We are in the process of setting up the first of these large driver pools here in FL.   Assuming we’re successful since it’s an operational solution, we’ll be able to replicate it anywhere these same types of trucking operations and market conditions exist.

Technically, we’re marketing an operational efficiency solution to our customers’ customers, but the way we’re doing it should allow us to grow considerably faster while better balancing liquidity and remaining cost-effective.

Where do you see your company headed next?

We have some exciting things on the horizon.  There are two pieces of legislation that individually could have a significant positive impact on us.  One is AB5 in California, which is currently at the US Supreme Court; the other is the PRO Act, which is currently in the US Senate.  Both negatively impact a subset of trucking companies by essentially outlawing how they use a certain type of driver.  If the laws affect the industry, the companies and the drivers won’t have many options.  Our marketplace is a low-cost, simple, fast, and effective alternative that easily integrates with their operations.

Also, a couple of universities have asked us to take part in a joint study about our marketplace, the operational model we create, the resulting industry efficiency gains, and the benefits for both trucking companies and drivers.   We’re especially excited about this because, from a startup perspective, academic validation is always good!

Additionally, India’s driver situation is in rough shape after COVID, and we have been told by a few people there that it could benefit from our operational model.  We’ve studied the situation, made some key contacts, and developed our strategy.  It’s in our sights, and our plan is to head there as soon as we are able.

Give us a tactical piece of advice that you'd share with another founder just starting out.

If you have a startup in Tampa, join Embarc Collective! The people are outstanding, and the facilities are top-notch!! If your startup isn’t in Tampa, don’t underestimate stealth, be fluid but directed by your vision, and keep moving.

Why Tampa Bay?

We’re opening up shop in Tampa because the business climate is excellent for what we do, the local talent is outstanding, the cost is comparatively low, and the community at large is very supportive. Not to mention, it’s just a terrific place to be if you like beaches, seafood, or professional sports!

Embarc Collective
Embarc Collective helps Tampa Bay’s startup talent build bold, scalable, thriving companies. Our staff of executive advisors and function-specific experts deliver individualized support to startups inside of Embarc Collective’s state-of-the-art 32,000 square foot hub.