Role description
CustomGPT.aiCustomGPT.ai is a profitable, bootstrapped AI company. We help organizations deploy AI agents on their own content - accurate, secure, and grounded in their own documents. Thousands of paying customers. No VC. Real product-market fit.
Professional associations are our fastest-growing market. Associations sit on decades of member content - journals, standards, certification guides, conference recordings - and their members want answers right now. National and state associations are already running member-facing AI on CustomGPT.ai. We're going all-in on this market.
Why this role exists
We need a hunter. Someone whose whole job is to get association executives into a first meeting with us - 20 qualified meetings every month. You book the meeting. Our Account Executives run it and close it. That's the deal.
What you'll do
Book 20 sales-qualified meetings a month with association decision-makers: CEOs, Executive Directors, COOs, CIOs, and heads of membership, education, and member services.
Work inbound hand-raisers fast: free signups, demo requests, abandoned checkouts, and intent signals — first touch inside 60 minutes.
Phone first. Then email, LinkedIn, and in person.
Travel ~5 days a month to association conferences (ASAE, state association societies, AMC events). Pre-book meetings before you land, work the floor, follow up the same week.
Use AI on the back end (Claude / ChatGPT for account research, lists, and call prep). Human on the front end of every conversation - no AI slop.
Log everything in HubSpot the same day. If it's not in HubSpot, it didn't happen.
Sit in our Needham office, next to our CEO and your SDR teammate. You report to our Head of GTM.
Who you are
Hungry. This is not a 9-to-5. Our buyers are coast to coast, so we work California hours.
1- 3 years as an SDR/BDR, in inside sales, recruiting, or any job where you got paid for results. Standout new grads with proof (athletics, a business you ran, top of a commission board) - we want to hear from you.
You love the phone. 100+ dials a day doesn't scare you; it's how you win.
Coachable. You listen back to your own calls and fix one thing every day.
Smart and AI-curious. You already use AI tools to work faster, and you want a career in AI.
Integrity. You log the truth, including the no's.
Why this is career-defining
AI is the biggest shift in business software in a generation. Learn to sell it from the inside, at a profitable company that's winning.
Direct access to the CEO. Your numbers show up every week, and so does the recognition.
A clear path: consistent 20-meeting months earn you a closing book and the path to Account Executive.
Compensation
$96K OTE: $48K base + $48K at-target variable, paid per qualified meeting.
Uncapped, with accelerators above 20 meetings a month. Top performers earn more than OTE.
Stock options in a profitable, bootstrapped company - no VC dilution, no liquidation preferences.
Health insurance and PTO.
Conference travel fully covered.
This is an on-site role in Needham, MA, five days a week, with ~5 travel days a month.