I want to describe what actually happened, not the version we put in the quarterly update.
We gave our sales team access to an AI assistant connected to our CRM, our product documentation, our past proposals, and our win/loss analysis. The pitch was straightforward: faster proposal drafts, better call prep, smarter objection handling based on what had worked historically.
Eighteen months later I have a clear picture of what changed, what did not, and what I would do differently.
The thing that changed the most was not what I expected. I had anticipated productivity gains around proposal drafting, which happened, and around call preparation, which happened partially. What I did not anticipate was how much the AI changed the internal dynamics of the sales team itself.
Before the AI, institutional knowledge about what worked in our sales process lived primarily with the senior reps. They had been through hundreds of deals. They knew which objections were deal-killers versus which ones were negotiating postures. They knew which product features actually mattered to which buyer personas. They knew how deals typically progressed at each stage. New reps learned this by sitting with senior reps and by losing deals and doing retrospectives.
