Job Description

Location: Needham, MA (On-Site)

About CustomGPT.ai :

Last week, GAI Insights named us one of the " Top 7 Emerging Leaders in AI ," placing us alongside OpenAI, Google, Microsoft, Anthropic, Cohere, and Meta. Our no-code AI platform brings custom AI to mid-market and SMB firms allowing them to gain value from Generative AI using their own data – delivering clear results and rave customer reviews.

We’re profitable, bootstrapped, and forging our own path without the constraints of traditional VC funding. This is a rare chance to join a company where you can shape strategy, drive revenue, and help define the playbook in a rapidly evolving industry.

The Opportunity:

We’re looking for a driven, entrepreneurial Senior Sales Executive who thinks like a founder. This is not a routine “check-the-box” sales role. Instead, you’ll own and accelerate every part of the sales process—from identifying key market segments and closing flagship accounts, to developing strategic land-and-expand approaches that will influence our roadmap.

As you excel, you’ll have the opportunity to establish and lead our sales team, playing a pivotal role in the company’s long-term growth.

Key Responsibilities:

• Strategic Prospecting & Business Development: Identify and target high-value opportunities in the generative AI space. You’ll build and refine pipelines from the ground up.
• Full-Cycle Selling: Lead high-level discovery calls, deliver compelling demos, handle negotiations, and close deals that drive meaningful revenue.
• Land-and-Expand Growth: Engage deeply with customers to expand accounts after the initial sale, ensuring long-term, scalable growth.
• Market Feedback & Product Influence: Provide direct input to product and marketing teams, shaping the product roadmap based on real market intelligence.
• Process & Team Building: Lay the foundations for a formal sales organization—refining sales operations, metrics, and best practices. Over time, lead the hiring and mentorship of junior reps.

What We’re Looking For:

• Experience & Tenacity: 5+ years out of college, with at least 3+ years in a strategic or enterprise sales role. A track record of consistently exceeding quota and winning complex deals.
• AI & Tech Enthusiasm: Demonstrable passion for AI technologies. You should be conversant with current AI market trends, able to speak credibly about value propositions, and excited by cutting-edge innovation.
• Ownership Mentality: A scrappy, resourceful mindset—comfortable working in a fast-paced, evolving environment without the safety net of big budgets or established playbooks.
• Communication & Influence: Exceptional storytelling, consultative selling, and negotiation skills. Able to translate technical capabilities into compelling, outcome-focused narratives.
• Builder DNA: You enjoy creating something out of nothing—refining messaging, process, and playbooks as you go.

Compensation & Benefits:

• Base Salary: Competitive (e.g., $100K–$150K range)
• OTE: $200K–$300K+ (with accelerators for overperformance)
• Equity: Meaningful stock options with standard 4-year vesting and a 1-year cliff, giving you real skin in the game.
• Performance Bonuses & Profit Sharing: Additional incentives linked to key revenue and profitability milestones.
• Comprehensive Benefits: Health.
• Growth Path: A clear trajectory to become our Head of Sales as you deliver results and help scale the team.

Location:

On-site in Needham, MA. This role is hands-on and collaborative, with daily in-person interactions to drive strategy and execution.

Ready?

If you’re craving an environment where you can flex your entrepreneurial muscles, leverage a world-class AI platform, and directly impact the company’s trajectory, let’s talk. Join CustomGPT.ai and help shape the future of generative AI sales—yours and ours.

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