The Training Business Newsletter
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TL;DR: Welcome back. At its peak, DevelopIntelligence ran on a network of 300 contractor instructors. None of them were employees. That wasn't a financial workaround, it was the model that let a bootstrapped training company compete with firms ten times its size. This week: how the contractor model worked, why fast payment was the real moat, and what broke when we scaled past 150 contractors.
The Contractor Model
Most training companies treat contractors as interchangeable labor. They pay slow, assign work based on availability, and compete for talent on price. We did the opposite.
We paid premium rates. We gave instructors interesting Fortune 500 engagements instead of generic classroom work. We invested in real relationships, with some instructors working with DI for over a decade. And we paid net-15 when the industry standard was net-60.
The result was a virtuous cycle. The best instructors chose DI. Better instructors delivered better training. Better training drove client retention. Higher retention funded better rates, which attracted even better instructors.
By the time competitors tried to replicate the model, we had a decade of relationships they couldn't buy.
The leverage wasn't just in delivery quality. With no employee instructor payroll, we scaled cleanly when demand surged and stayed profitable when it dipped. That's the model most training companies need and few build.
The Cash Flow Engine
Paying contractors fast isn't free. Enterprise clients pay net-30 to net-60. Contractors were on net-15. Something has to fund the gap.
For us, that was the cash reserve with 12 months of operating expenses on hand, specifically to fund the working capital gap between paying contractors quickly and collecting from clients slowly. Without that reserve, we couldn't have paid fast. Without paying fast, we couldn't have attracted top contractor talent. Without top talent, the model wouldn't have compounded.
It's not an accounting detail. It's a strategic system. The cash reserve and the contractor model only work together.
What Breaks at Scale
The contractor model has one hidden cost: it's operationally expensive.
At 50 contractors, our operations lead knew every instructor's strengths, availability, and client preferences. Scheduling was a series of phone calls. It worked.
At 150, the spreadsheets started to crack. Instructor matching depended on tribal knowledge that lived in one person's head. Key-person risk became real.
At 300, the bottleneck wasn't content or sales. It was delivery operations. Scheduling a single engagement took days or weeks. Matching instructors to clients was a full-time job. Materials, travel, last-minute changes ate hours every week.
The uncomfortable truth: most training companies don't hit a revenue ceiling because of demand, content, or talent supply. They hit it because their back office can't schedule fast enough.
Run training? You need delivery infrastructure.
TryTami automates instructor matching, scheduling, and logistics so training companies can scale their contractor networks without scaling their back-office headcount. It's the delivery infrastructure that took DevelopIntelligence 18 years to figure out, built into AI-native software.
Schedule a demo below:
Thanks for reading,
Kelby and Dave
About the Authors
Kelby founded DevelopIntelligence, an instructor-led training business, and grew it to $12M in revenue before the acquisition by Pluralsight. He's building TryTami to automate the operational playbook that made his previous training business work.
Dave is Head of GTM at TryTami. He helped grow DevelopIntelligence with Kelby and has experience at multiple EdTech companies.
