Sales Development Representative

About the Role

CustomGPT.ai is a profitable, bootstrapped AI company helping organizations deploy AI agents on their own content: accurate, secure, and grounded in their own documents. This role is for a hunter focused on getting association executives into a first meeting.

Key Responsibilities

• Book at least 20 qualified meetings a month with association CEOs, Executive Directors, COOs, and heads of membership, education, and member services.
• Make 100+ dials a day on a parallel dialer, working a scored list of 10,000 association contacts. Prioritize phone, then email, LinkedIn, and in person.
• Build your own lists and call blocks.
• Work inbound hand-raisers (free signups, demo requests, abandoned checkouts) within 60 minutes.
• Travel as needed to association conferences (ASAE and state societies) to pre-book meetings, work the floor, and follow up.
• Multi-thread alongside Account Executives (AEs) and the CEO on hot accounts.
• Log every call in HubSpot the same day, including rejections.

Requirements & Tech Stack

• Phone-first approach, preferring calls over email sequences.
• Coachable and willing to listen to and improve from call recordings.
• Honest and transparent about performance.
• Credible with executives through quick research, a specific reason to call, and direct communication.
• Fluent in or able to become fluent in week one with: HubSpot, Sales Navigator, Apollo, Nooks, Claude.

Qualifications

• Proven experience as an SDR or BDR with a verifiable meeting or pipeline number, or at least 6 months of such experience.
• Alternatively, demonstrate hitting hard goals with no direct supervision (e.g., athlete, founder, top performer on a commission board).
• Committed to booking meetings for at least the next 18 months.
• Not a student or transitioning into sales for a trial period.

Work Environment & Compensation

• On-site in Needham, 5 days a week.
• Startup hours: approximately 50 hours a week, including full Fridays.
• Afternoon call blocks may extend late to reach the West Coast.
• OTE: $96,000+ with uncapped variable compensation based on performance.
• Variable pay structure:
• $100 per qualified meeting held.
• $75 when the meeting advances to discovery.
• 2% of first-year contract value when the deal closes.
• Includes stock options, health insurance, and paid time off.

Career Growth

• Opportunity to grow the role into a closing book, account management, or leading the next SDR, based on results.
• Reports to Jon Kaplan, VP of Go-to-Market.
• Sits in the Needham office alongside the CEO and SDR teammate.