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)