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When DevelopIntelligence started in the early 2000s, enterprise technical training was a commodity. Generic courses. Generic instructors. Generic outcomes.

Large companies had a different problem: they needed their own programmers trained on new technology, and they needed it fast. Nobody in the training industry was built to serve that need.

So we built a different model.

The belief: People learn by doing. Not by watching lectures. Not by taking tests. By working through real problems with an expert who knows what they're actually doing.

The model: Outsourced technical training. We recruited expert contractor instructors — people still coding, still solving real problems in production. We deployed them on-site at client companies for weeks at a time.

The client: Fortune 500 companies that needed to retrain their engineers before technology changes left them behind.

The outcome: The market gap was real. Demand was strong. Retention was high. The business grew steadily for 18 years.

Takeaway: A tight niche with a clear unmet need beats a broad market with weak differentiation.

Here's the decision that shaped everything else: we kept 12 months of operating expenses in cash.

This wasn't conservative. It was strategic.

Enterprise sales cycles are long. Six to nine months from conversation to contract is normal. If you're running on tight margins, you can't afford to wait. You get desperate. You cut corners on hiring. You take on bad clients. You price too low. You burn out your team trying to grow faster than your business can actually support.

The 12-month reserve changed the game.

It meant we could wait for the right people. Sales is the highest-leverage hire in B2B services. One great sales person compounds. One bad hire costs months of lost revenue. We could be selective because we weren't desperate.

It meant we could invest in relationships. We visited clients. We learned their problems. We showed up as consultants, not vendors. This took time. It built trust. It created word-of-mouth that worked for years.

It meant we could pay contractors in two weeks instead of two months. Industry standard was net-60. We offered net-15. Better instructors have options. If you pay fast, they choose you. Better instructors do better work.

It meant we could say no to bad deals. When you have a year of runway, you can walk away from a contract that doesn't fit. You can avoid the race to the bottom on pricing. You can protect your margins and your culture.

All of this added up to one thing: financial discipline created a talent moat. Better instructors chose to work with us. Better instructors meant better outcomes. Better outcomes meant clients came back and recommended us. That compounds. After five years, we had a waiting list.

Takeaway: Cash reserves aren't boring. They're the foundation for operating from strength.

Here's the thing about the DI playbook: it works because the fundamentals are solid. But it's fragile to execute.

We managed 300+ contractor instructors, complex multi-client scheduling, travel logistics, payment tracking, and compliance on spreadsheets. Excel and email. It worked. But it was like flying a plane while manually checking every gauge.

One scheduling mistake cascaded into missed contracts. One payment delay broke a relationship. One wrong instructor assigned to a client created a project failure that took months to recover from.

If you're starting a training business today, or scaling one that's on spreadsheets, there's a better path: software that handles the operational complexity so you can focus on clients and instruction.

That's what we're building with TryTami.

The platform automates what DevelopIntelligence did manually: instructor management, scheduling across time zones and client needs, logistics coordination, payment tracking, compliance, reporting. It lets you manage a network of dozens or hundreds of instructors without the fragility.

The result: you can operate with the financial discipline and client focus that made DI work. But without the operational heartburn.

If you're running a training business on spreadsheets, or you're thinking about starting one, that's worth a conversation.

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 spent 15 years building and scaling B2B SaaS companies. He helps training businesses understand the financial and operational dynamics that drive growth.