Enterprise Sales Leader, Retail

Sierra is building a platform to enable every company to create better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. Our co-founders are Bret Taylor and Clay Bavor.

The Retail team partners with a large and growing number of retailers across apparel, beauty, grocery, big-box, home, auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members daily with order tracking, returns, product discovery, booking services, and issue resolution. Retail is also where AI agents go beyond support to generate revenue through product discovery, personalized recommendations, cart recovery, win-back campaigns, and in-store support.

• Lead and develop a high-performing sales team: hire, onboard, and develop AEs across your region; coach on deal strategy, pipeline management, and execution; create a culture of accountability, learning, and collaboration; identify and grow future leaders.
• Own regional performance: own your regional number and forecast accuracy; inspect pipeline quality and unblock stalled deals; drive consistent execution of the sales process; partner with RevOps to ensure clean data and clear insights.
• Be deeply involved in deals: join key customer and prospect conversations; help reps navigate complex buying committees and late-stage deals; support pricing, negotiation, and close strategy.

• 10-15+ years of experience in enterprise customer-facing sales, identifying and closing large accounts.
• 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
• Experience running and managing end-to-end complex deals ($1M+).
• Exceptional verbal and written communication abilities.
• Analytical mindset to analyze market trends, identify opportunities, and make data-driven decisions.

• Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
• Experience building GTM strategies and sales teams from scratch or early-stage growth.

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, snacks, and coffee
• Discretionary benefit stipend
• Eligible full-time employees can participate in Sierra's equity plans