When I tried to grow our sales team, I struggled. Everything changed when we started using outbound AI. I’ll walk you through how we tripled our pipeline without hiring more people.
What I've Learned From 77 Companies
Across 234 angel investments, including Anthropic, a few patterns in outbound AI come up again and again.
The founders who handle outbound AI well understand that the best solutions are often the simplest ones.
The Counterintuitive Truth
In outbound AI, the best practitioners often do less, not more.
The lesson: most founders overthink this and underspend on execution. It sounds simple. It's incredibly hard to execute.
The Reality Nobody Talks About
A lot of the advice on outbound AI rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that customer feedback is the only metric that matters. I've seen this play out across dozens of companies. The pattern is unmistakable.
Many teams spend months on the wrong path before realizing that the best solutions are often the simplest ones. Once they make the switch, everything changes.
What I Tell Founders
Before deciding anything about outbound AI, start with three questions:
What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around deal scoring AI, conversational sales AI, outbound AI, AI sales tools, AI CRM that I've been thinking about a lot lately.
What's Next
Best practice in outbound AI is changing fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
If you're building in this space, the best time to get outbound AI right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
Frequently Asked Questions
Q:How long did it take to see results?
Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.
Q:Can these results be replicated?
The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.
Q:What would you do differently looking back?
I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.