Good Morning. Happy National Candy Corn Day! A holiday dedicated to the worst candy ever made. Tomorrow’s Halloween and the end of the month, which means there’s officially 2 months left to hit your 2025 quota. And let’s be honest... that’s a lot scarier than any haunted house. Happy selling out there, my friends. Now, let’s get into today’s Follow Up. (:
Call out the friction 🗣
Replacing a sales team w/ AI agents 👀
Getting too close w/ your prospect’s family 📱
Sales jobs & a meme 😂
Sales Tip of The Day 💡
When you sense a buyer is holding back, call it out gently instead of ignoring it.
❌ “Sounds great—let’s keep things moving.”
✅ “I might be reading too much into this, but it sounds like you’re not 100% sold yet. What’s giving you pause?”
This helps build immediate trust by showing emotional intelligence and turns friction into a conversation.
You can’t overcome an objection if you don’t know what it is.
Unlock Trapped Data with Essential Apps for Sales.
Too often, valuable insights get trapped in siloed tools.
The 2025 Essential Apps for Sales collection features 14 curated apps that, paired with HubSpot, help you easily put your data to work in your next report, workflow, segment, or sync.
Vercel’s Just Replaced Their Sales Team With AI
Vercel, a $9.3 billion cloud company, just did what most tech leaders only whisper about.
They replaced nearly their entire inbound sales team with AI agents.
And so far… it looks like it worked.
AI replacing salespeople is no longer a “maybe someday” story about the future. It’s happening, right now.
Here’s how they did it, what happened to the humans, and what this means for the future of sales. 👇
What Actually Happened
Vercel had a classic inbound sales team: 10 reps, all handling leads, qualifying prospects, and sending follow-ups.
Leadership thought that a lot of their work could be automated, so they made a bold move.
They picked their best sales rep and had engineers track every step of their workflow.
Then, the engineers built custom AI agents to do the same job.
A human manager checks the agent’s work in Slack and gives feedback to improve how the agents work.
After implementing the agents, the 10-person team shrank to 1 human & a team of agents.
How They Built the AI Agents
This wasn’t just “turn on ChatGPT and hope for the best.”
They picked their best sales rep and had engineers shadow every step of their workflow for six weeks. They wanted to know the exact steps they took and how they made decisions.
Every click, every email, every decision. Everything documented.
The bot reviews inbound messages → filters spam → qualifies leads → drafts a custom email and routes support tickets to the support team.
The agents also have access to the company’s internal databases and use OpenAI’s Deep Research tool to qualify inbound leads and write personalized replies.
The key to making this all work was their emphasis on automating the best practices.
In many cases, if you can document a workflow that repeats itself, you can train an agent to do it.
What Happened to the Sales Reps?
No need to worry about the 9 sales reps that got replaced.
Vercel moved them into outbound prospecting, which they say “is higher-value, more complex sales work.” (aka, something that can’t be automated as easily).
COO, Jeanne DeWitt Grosser says the goal isn’t to cut headcount. It’s to shift humans to creative, challenging work. The stuff that AI can’t do (yet).
Entry-level, repeatable tasks? That’s the AI’s job now. Humans focus on complex deals and building relationships.
Vercel’s headcount actually grew last year, and the company is betting that AI will handle the busywork, while people do what bots can’t.
What Does the Future Look Like?
Vercel’s strategy is something we’re likely to see more of in the coming months.
Train AI on your best people.
Automate the repeatable stuff.
Let humans focus on what’s creative, ambiguous, and high-value.
For sales teams everywhere, this is a wake-up call. Entry-level roles that act as order takers are getting automated.
The future of sales is humans doing what bots can’t: building trust, solving complex problems, and making real human connections.
It’s still too early to know how AI experiments like Vercel’s will play out. But there’s no denying that AI will have a spot on the sales team.
Would you trust an AI agent to handle your inbound leads?
