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For the first several years, DevelopIntelligence sold training through resellers and channel partners. They brought the client, we delivered the work. The arrangement was easy. The margins were 15%.

Not all revenue is equal. Reseller revenue comes with structural limits: you don't own the relationship, you can't expand accounts, and an acquirer discounts it because it depends on a third party. That's not recurring revenue. It's rented revenue.

Going direct to enterprise changed the math entirely. Full margins on every engagement. Direct relationships that compounded over years. Data on what clients needed next. Pricing power based on expertise instead of competing on cost.

More importantly, it forced us to build real sales infrastructure and direct client relationships that an acquirer could underwrite. Revenue you own and can grow is worth multiples more than revenue that depends on someone else.

Going direct was the single decision that made DevelopIntelligence a business worth acquiring.

Going direct forced us to build a sales engine from scratch. That meant learning what works in training sales, and what doesn't.

The instinct is to hire aggressive closers. In most B2B, that works. In training, it backfires. The buyer isn't purchasing a product. They're trusting you with their team's development. An aggressive close doesn't just fail. It damages the trust that the entire engagement depends on.

There's also a scaling challenge: at some point, the founder can't be on every call. Kelby knew the clients and could sell consultatively, but that doesn't scale. DI had to transition from founder-led sales to a team that could sell without him, codifying the founder's intuition into a repeatable process.

What works in training sales: consultative selling built on deep discovery. The most effective conversations at DI weren't pitches. They were sessions where we learned more about the client's problem than anyone else had bothered to. That depth became the competitive advantage.

The combination that worked: competitiveness and empathy in the same person. Someone who wanted to win, but won by understanding the client's problem more deeply than anyone else.

Enterprise training deals take months. The buyer involves L&D, engineering leadership, procurement, sometimes legal. A team optimized for speed will churn through prospects. A team optimized for relationship depth closes fewer deals at much higher value.

Four years before the acquisition, we implemented EOS (Entrepreneurial Operating System).

It gave us three things: clear accountability (every leader owned their numbers), weekly visibility (L10 meetings caught issues early), and quarterly focus (Rocks forced us to prioritize ruthlessly).

The real result: Kelby was no longer the bottleneck on every decision. The business could run without him.

During the 18-month transition to Pluralsight, DI grew from $12M to $17M. That growth happened because the business had systems. It didn't depend on any single person.

If your training business can't run without you, that's the gap to close first.

The Training Business Playbook covers everything:

The bootstrap model, contractor economics, going direct to enterprise, building a sales engine, implementing EOS, and the $49M exit.

Learn more about the challenges we ran into and how we solved them.

Get it here:

Thanks for reading,
Kelby and Dave

About the Authors

Kelby founded DevelopIntelligence, an instructor-led training business, and grew it to an 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.