Enterprise Sales Director - Strategic, Retail

About the Retail team

• 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.

What you'll do

• 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.

What you'll bring

• 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.

Even better...

• 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.

Our values

• Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.

• Flexible (unlimited) paid time off

• Life insurance and disability benefits

• Retirement plan dependent on country of employment

• Parental leave

• Fertility and family building benefits

• Free alphorn lessons