Enterprise Sales Director - Strategic, Retail

- Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand's own voice.

- Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand's top line - not just its cost line.

- Join us to transform how the world's most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.

- Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.

- Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.

- Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.

- Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.

- Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.

- Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

- 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.

- Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.

- Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

- Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.

- Mastery of complex deal structuring, risk navigation, and pricing.

- Exceptional executive communication and a reputation for precision and trust.

- Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.

- Experience operating alongside founders/executives in front of strategic customers.