Sales Development Representative

CustomGPT.ai; Needham (MA); On-site; USD 90,000 - 120,000; Full time

Benefits offered by this job

Stock options

Health insurance

PTO

Conference travel fully covered

Job summary

CustomGPT.ai is hiring an SDR/BDR to drive growth with associations. This on-site role in Needham, MA focuses on booking 20 qualified meetings monthly, handling inbound signals quickly, and engaging executives by phone, email, LinkedIn, and in-person visits.

You will join a small team, work closely with the CEO, and use AI to prep calls while maintaining human-first conversations. 1–3 years of inside sales experience is preferred.

Qualifications

• 1–3 years as an SDR/BDR, inside sales, or results-driven roles.
• Willingness to work California hours for coast-to-coast buyers.
• Excellent phone skills and fast follow-up.
• Proven track record of meeting or exceeding activity goals.

Responsibilities

• Book 20 sales-qualified meetings a month with association decision-makers.
• Respond quickly to inbound signups, demos, and intent signals.
• Primary outreach via phone, then email, LinkedIn, and in person.
• Travel ~5 days a month to association conferences.
• Research accounts with AI tools and prep calls for executives.
• Log all activity in HubSpot the same day.
• Report to Head of GTM from the Needham office

Skills

Phone sales

Cold calling

Coachable

AI-curious

Tools

HubSpot

Job description

CustomGPT.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.