AI Outreach Pipeline.

Vertical Raise reps ran on walk-ins and referrals. Jason, their top seller, held a large but disorganized Excel list of high-school coaches. Drafting cold emails by hand was slow enough that he rarely touched the list at all. The asset was not the problem. The cost of acting on it was.

I put the draft in Gmail for review rather than sending automatically. Jason's advantage was that he knew this world, and cold outreach to high-school coaches fails the moment it reads generic. Automating the blank page rather than the send kept his judgment in the loop where it created value and removed it from where it did not.

• De-duplicated and normalized 2,000+ coach records: school, sport, last fundraiser date, email.
• ClickUp as a lightweight CRM with a Kanban pipeline: Target, 1st Email, Follow-up, Demo Booked, Won/Lost.
• Make.com watches the 1st Email stage and triggers Claude to pull school and sport variables, generate a personalized intro with fundraiser value props and a CTA, and save the draft in Gmail for rep review.
• A 30-minute Loom walkthrough and quick-edit checklist so he could tune tone and send at scale.

>500%

increase in weekly outbound, about 5 to 25+ emails

5

new fundraising programs signed within 21 days