Automated follow-up to improve speed and consistency

I broke up with ChatGPT. 2 years together. Walked away.

Every session felt good. Warm. Encouraging. But my deals weren't closing faster.

I'd ask for objection handlers. Get 11 seconds of typing. Then a response that validated my approach and left me with more options than clarity. ChatGPT treated me like someone who needed support.

I needed a closer.

5 months ago, I tried Claude.

Pasted a stalled deal. Asked why the prospect went dark.

"Your last email buried the value prop. Here's the exact follow-up that reopens this conversation."

Brutal. Specific. Ready to send.

I don't need AI to validate my outreach. I need it to tell me why the deal stalled and how to unstick it.

Team Claude or team ChatGPT?

A quick and dirty outreach system for founder-led sales. Bonus, it won't make you hate yourself:

1. Create a project in Claude or ChatGPT and call it something like “sales and business assistant.” Drop in a detailed explanation of your ICP, strategy docs, transcripts of sales calls. This becomes your operating system for outreach, planning, and prospecting.

2. Request a data export from LinkedIn (settings -> privacy -> data). Takes them about 24 hours to send you a CSV of your connections.

3. Drop it into your AI project alongside your targeting framework and ask it for a list of people you should reach out to; ask it to include a score for each. Half the results will be wrong. Tell the AI why. You will eventually get your first 10 to 20 people to reach out to, and your AI project will get smarter.

4. Start a chat inside your project called “leads” or “prospects.” When you’re ready to message someone, screenshot their LinkedIn profile, drop it in, and ask the AI to draft a message. Refine heavily because the draft will make you want to claw your eyes out. Again, the AI will get smarter over time. Human edit always.

5. On the message itself: don’t do the fake “I saw your post about X and it really resonated with me” thing. That is insufferable. Just be human and make the ask clear.

6. Send 15-30 LinkedIn connection requests a week to grow your audience. Build lists of people in Clay on the free tier and enrich your lists with their LinkedIn profiles. Or just search manually on LinkedIn.

7. Track who you’ve messaged. Google doc with name + the last action you took. Mine is ugly but it keeps me honest, and my exec assistant uploads it to HighLevel.

8. You can have Claude Cowork scan your list and set reminders on your calendar to follow up with people if appropriate. It can even include a drafted follow-up message in the event notes to keep you from procrastinating when it's time to send a nudge.

9. Write at least one LinkedIn post a week, ideally two. This is fuel for everything else. Your content is what warms people up after they accept your connection request.

10. Audit your LinkedIn headline and about section. Your profile + content is how people decide if you’re worth paying attention to, and it’s important to the new algorithm.

11. The only metric that matters when you start is “did you do your actions this week.” Fifteen to twenty-five. You can’t control who says yes to a demo but you can control whether you did the work.

If you get into a good groove, keep the momentum going. It’s tough to slow down and have to rev the whole engine back up again.

What am I missing?

There’s a lot of talk about AI and automation “replacing” people in sales, especially in industries like construction where relationships still carry most of the weight. I don’t buy it.

I love tech and rely on automation daily. But let's be honest. We can all spot an AI-generated message from a mile away. You just know when you are reading something written by a bot. The true value of these tools isn't in trying to fake a human connection. It's in cutting out the background busywork so you have the time to actually talk to people yourself.

3 ways automation actually makes us more human in sales:

1. Less admin, more face time.
When you’re not buried in spreadsheets or chasing down email threads, you can spend more time on the calls and meetings that actually move deals forward. The tech handles the repetitive stuff so you can focus on the conversations that matter.

2. Faster follow-up, better trust.
Automated systems mean nobody falls through the cracks. Prospects get a quick response, even if it’s just to set up a real conversation. That consistency builds trust, something you can’t fake with a template.

3. More energy for the hard parts.
Sales in construction and tech isn’t about blasting out emails. It’s about listening, problem-solving, and building credibility over time. Automation frees up the mental bandwidth to do the real work: showing up, following through, and closing deals face-to-face.

I’m curious. How are you all balancing new tech with old-school relationship building?