Strategic Account Executive at Raspberry AI

About The Role

We’re hiring Strategic Account Executives in New York, Los Angeles or Portland to lead full-cycle, enterprise-level deals across fashion, travel, home goods, lifestyle brands and other retail brands.

The right AE will combine enterprise rigor, resourceful outbound creativity, and executive polish—driving annual and multi-year contracts through multi-threaded relationships.

This is a scaling role for reps who’ve already mastered structured selling and want to build repeatability in a high-growth AI startup.

You’ll be part of the GTM team driving Raspberry AI’s next stage of growth—helping define what elite, value-driven enterprise selling looks like in the AI era. This is a high-ownership role for operators who thrive in ambiguity, move fast, and turn every touchpoint into momentum.

Responsibilities

• Own the full sales cycle: prospect → qualify → demo → negotiate → close → expand.
• Develop multi-threaded relationships across Marketing, Innovation, IT, and Procurement.
• Craft ROI-driven executive narratives and business cases.
• Run 3–6 month cycles with focus on annual contracts, expansion, and retention.
• Build creative pipeline through outbound, phone, events, and social proximity—not just sequences.
• Collaborate with Product, CS, and Marketing on account strategy.
  
  

Requirements

• 8–10 years of B2B SaaS closing experience, ideally $250K–$750K+ ACV.
• Proven success in enterprise / upper-mid market deals with multi-stakeholder complexity.
• Demonstrated ability to own negotiations end-to-end, from commercial structure through contract execution. Comfortable navigating legal, procurement, and compliance processes directly.
• Experience pricing and packaging complex, usage-based or credit-consumption models, not just seat-based licenses.
• Deep experience with outbound prospecting and self-sourced pipeline creation.
• Strong negotiation skills, MEDDICC fluency, and forecasting accuracy.
• Experience selling AI, creative, or marketing technology is a plus.
• Excellent communication and interpersonal skills, with the ability to build and maintain relationships with stakeholders at all levels of an organization.
• Hungry, curious, resilient, and relentlessly resourceful.
  
  

Compensation

• This role will receive a competitive On-Target Earnings $300k+ (base salary + sales commission) + benefits + equity
• Quota: ~$1M
• Location: NYC, LA or Portland (remote)
  
  

Compensation Range: $250K - $350K