Trying my best to be mindful & intentional
Joined June 2009
- Tweets1.2K
- Following189
- Followers262
- Likes460
v1 of my follow-up system: HubSpot tasks.
Every follow-up became a task, on top of the tasks our call recorder created after every meeting. Within weeks I had a wall of overdue tasks I wasn't getting to.
The CRM turned into a guilt list.
7 months ago I took my biggest career bet.
I walked away from a $450K VP Sales role to take a job with a made-up title: “VP of Autonomous GTM” at Swan AI.
I built a fully autonomous one-person GTM org. I hit $1M+ of pipeline a month with just me & AI agents.
Most folks in GTM think you want more pipeline coverage, not less.
But Manny Medina (Outreach co-founder) told me the best AI-native companies he speaks with average 1.7x pipeline coverage.
Historically, we've always been told 3-5x.
Two thirds of our MQL alerts. 19% of pipeline. Deals 65% larger than average. All from signals we were already getting.
The best signal-based outbound I've built didn't start with a new signal.
At Swan AI, our best organic inbound source is LinkedIn.
Every new sales rep gets a ramp. I gave the agent the same grace.
I won't ever know where the boundary is if I don't push the limit.
My follow-up system went through 5 versions this year. The first four each broke in a new way.
v5: My own follow-up app. Under 10 minutes to clear the day.
Turns out, the busy work was never the writing. It was everything around it.
So I had to treat the AI like a 4 year old - to ask questions I'd never asked software before.
What failed? Why? How do we prevent this next time? Maybe we break it into smaller chunks?
Weird questions to ask a machine. But the machine had answers.
"Very unprofessional Jeremy." A CEO emailed me that after I cancelled our meeting. He ended with "Everyone's time is valuable." He was right. It's also why I still cancel meetings.
I don't need more meetings & opportunities. I need fewer, higher-quality ones.
We're generating $1M+ of pipeline per month with 1 GTM person (me) + AI agents.
Gold leads went fully autonomous.
The outreach agent gets it right 70-80% of the time. If 70% quality means processing 2 or 3x more leads, the net is massively positive.
AI isn't a 1 shot technology. It doesn't just work.
The people on the other side of this revolution aren't the ones AI worked for on the first try.
They're the ones who kept going when it didn't. That's the rep. That's the work.
First week at one of the hottest AI GTM startups. Full pipeline. No team. What was my first move? Turn the AI off.
Turns out, you can't automate judgment you haven't developed yet.
Automation is a force multiplier. It multiplies whatever you feed it. Including the broken stuff.
Automate last, not first.
A client asked me last night how many customers we have. Then asked how many employees. Hundreds. And 7.
I think I broke his brain.
Even the best AI customer service agent doesn't get you to hundreds of accounts alone. What gets you there is the people that stand behind it.
Partner teams implement Swan shoulder to shoulder with us, then stay on afterwards as the ongoing service layer.