Enterprise Sales Leader, 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

• Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.

• Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our 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.

What you'll bring

• 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.

• People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.

• Enterprise experience: You've run and managed end-to-end complex deals ($1M+).

• Strong communication skills: Exceptional verbal and written communication abilities.

• Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.

Even better...

• Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.

• Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.

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 through Carrot

• Free alphorn lessons