Over 50% of our small sales team at SaaStr is now powered by AI.
We’re not chasing headlines or seeking to epitomize the AI revolution. Our goal is to learn, and perhaps we’re pushing more than most. The reality is more pragmatic—and human—than that.
The Learning Imperative (But That’s Not the Main Story)
Part of this is staying current. In the Age of AI, if you’re leading a B2B company and not actively incorporating AI, you’re already lagging. We believe we’re ahead of 95% of companies with four AI agents fully operational handling three sales types, plus support, content review, and community management.
This initiated our AI sales experiments but isn’t why we dove deep.
The Uncomfortable Truth: Tired of the Arguments
The real reason for deeper AI sales integration isn’t innovation or competitive advantage. It’s about operational sanity.
We were exhausted by recurring human dynamics draining productivity and patience:
- The Follow-Up Failures: “Did anyone follow up with the enterprise lead from yesterday’s demo?” Silence, scrambling, and then discovering the lead went cold due to lack of discipline.
- The Two-Week Expert Syndrome: New hires, with us for 14 days, questioning decade-refined strategies. The confidence-to-competence ratio was inverted.
- Generic Outreach at Scale: Team members sending templated messages to prospects, wondering why response rates were sub-1%, despite training and discussions on personalization.
- The Phantom Meetings: “No one was interested” often meant calls weren’t made or only one email was sent, revealing zero meaningful prospect engagement.
- CRM Black Holes: Encouraging sales reps to log activities and summarize meetings felt like negotiating treaties every week.
With AI, when our AI SDR mentions specific SaaStr events, congratulates roles found on LinkedIn, and suggests relevant programs based on profiles, it’s programmed to operate this way.
The standard we set: would I have written this email myself? The answer became yes consistently.
What AI Actually Delivers (The Unglamorous Reality) — And Why
Here’s what our AI sales agents accomplish to solve these issues:
- They follow up. Consistently, within timelines, and with relevant context from past interactions.
- They don’t contest proven methodologies. They execute our refined playbook.
- They personalize outreach by researching prospects beforehand, not out of preference.
- They log interactions with detailed notes immediately, by design.
- They work 24/7 without requiring vacation, sick days, or attitude adjustments.
The training reality: We dedicated the same time training AI as a human SDR—two intensive weeks, but could train at any time. For the first two months with AI chat, we spent 30 minutes every morning auditing conversations and teaching better responses to the AI. Now, it’s weekly.
The data requirement: Our