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Sales Strategy and Leadership for B2B Tech Companies

B2B tech sales moves faster than industrial sales, but the hard problems are the same: knowing how you win, building a team that can repeat it, and keeping discipline when the number gets tight.

What's different is the pace and the product. Cycles are shorter, buyers often try the product before they talk to anyone, and the pressure to grow can push hiring well ahead of a repeatable approach.

What makes tech sales different

  • Faster cycles. Mistakes show up sooner, and so do the effects of a bad comp plan or loose qualification.
  • The product sells first. Trials, free tiers, and usage data change what a seller's job is. The question becomes when a person should step in, and what they add.
  • Expansion matters. Growing existing customers can be as important as new ones, and the comp plan has to reflect which you actually want.
  • Founders sell well. Early deals often close on the founder's credibility and product knowledge, which a new rep doesn't have.

Where tech sales teams get stuck

  • Sales hires arrive before anyone can explain how deals are won, so each rep invents their own approach.
  • Nobody owns the handoff between product signups and sales conversations.
  • The team is measured on activity because outcomes are hard to read.
  • Top sellers become managers and spend their week on the forecast instead of developing reps.
  • Short-term pressure loosens qualification and pricing discipline, and those exceptions quietly become the strategy.

Discipline before scale

I think governance is underrated in growing tech companies. It isn't bureaucracy. It's deciding in advance which trade-offs you won't make under pressure: who you sell to, how you price, what you pay reps for. Teams that decide early spend less time undoing accidental strategy later. I talked through this on a podcast episode about building operating discipline before scale; it's on the media page.

Practical AI in a tech sales team

Tech teams usually have plenty of tools. The gap is a defined job for each one. Before adding another, finish this sentence: "We need to help [person] do [specific job] better, and we'll know it's working when [observable result]." If the team can't fill it in, the problem is the workflow, not the tool.

Where to start

Most tech companies I'd talk to are moving from founder-led sales to a team (build), fixing a motion that stopped working (rebuild), or preparing to grow (scale).

Work with Kevin

Tell me what needs to change in sales.

Share what you're building, rebuilding, or struggling to execute. I'll read your note personally and reply by email.