Sales Development Representative

CustomGPT.ai; Boston (MA); On-site; USD 86,000 - 106,000; Full time

Benefits offered by this job

Stock options

Health insurance

Paid time off

Job summary

CustomGPT.ai is seeking a results-driven SDR to book meetings with association executives. You will focus on generating 20 qualified meetings per month, leveraging a high-volume outreach approach across phone, email, LinkedIn, and in-person interactions.

The role emphasizes fast-paced, coachable performance, with travel to conferences as needed and close collaboration with the AE team. On-site in Needham, MA, with startup hours and a dynamic environment.

Qualifications

• At least 6 months as an SDR or BDR with measurable meeting or pipeline results.
• Track record of meeting or exceeding activity goals.
• Excellent phone/ outreach skills and coachability.

Responsibilities

• Book at least 20 qualified meetings a month with association leaders.
• Make 100+ dials a day on a parallel dialer.
• Build and manage prospect lists and blocks for outreach.

Tools

HubSpot

Sales Navigator

Apollo

Nooks

Claude

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. They sit on decades of member content (journals, standards, certification guides, conference recordings) and their members want answers now. National and state associations already run member-facing AI on CustomGPT.ai, and we are going all-in.

Why this role exists

We need a hunter. Your whole job is getting association executives into a first meeting with us: 20 qualified meetings held every month. You book the meeting. Our Account Executives run it and close it.

What you'll do

• Book at least 20 qualified meetings a month with association CEOs, Executive Directors, COOs and heads of membership, education, and member services.
• 100+ dials a day on a parallel dialer, working a scored list of 10,000 association contacts. Phone first, then email, LinkedIn and in person.
• Build your own lists and call blocks. Tomorrow's list is ready before you leave today.
• Work inbound hand-raisers (free signups, demo requests, abandoned checkouts) within 60 minutes.
• Travel as needed to association conferences (ASAE and state societies). Pre-book meetings, work the floor, follow up the same week.
• On hot accounts, multi-thread alongside our AE and CEO: you open doors, the AE runs the deal. Use AI for research and call prep, and keep every conversation human.
• Log every call in HubSpot the same day, including the no's.

Who you are

• Proven. At least 6 months as an SDR or BDR with a meeting or pipeline number you can quote. No SDR time? Show us you hit hard goals with nobody watching: athlete, founder, top of a commission board.
• Here for this job. You want to book meetings for the next 18 months. If your goal is closing deals or managing people within a year, this isn't the role.
• Phone-first. You'd rather call than send another email sequence, and you take a second swing at the objection before you hang up.
• Coachable. You listen to your own calls, and your next call is better than your last.
• Honest. You log the no's and flag a slow month before anyone asks.
• Credible with executives. Quick research, a specific reason to call, straight to the point.
• Fluent in the tools, or will be in week one: HubSpot, Sales Navigator, Apollo, Nooks, Claude.

Read this before you apply

• On-site in Needham, 5 days a week. Startup hours: about 50 a week, full Fridays.
• Our buyers are coast to coast, so afternoon call blocks can periodically run late to reach the West Coast.
• Not a fit if you're still a student, or moving into sales from another function to try it out.

Compensation

• $96,000+ OTE. Variable uncapped based on performance.
• How variable pays: $100 per qualified meeting held, $75 when that meeting advances to discovery, and 2% of first-year contract value when it closes.
• Stock options, health insurance and paid time off.

Where this goes

Own this seat and hit 20 meetings month after month, and we grow the role with you: a closing book, account management, or leading the next SDR. Earned with results. You report to Jon Kaplan, VP of Go-to-Market, and sit in our Needham office next to our CEO and your SDR teammate.

CustomGPT.ai is an equal opportunity employer.