Enterprise Sales Leader, Retail

Retail Team Opportunity

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.

Your Role

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.

Customer Obsession: We deeply understand our customers' business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.

Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn't right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.

Intensity: We know we don't have the luxury of patience. We play to win. We care about our product being the best, and when it isn't, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.

Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other's personal and professional achievements.

What We Offer

We want our benefits to reflect our values and offer the following to full-time employees:

• 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, as well as delicious snacks and coffee to keep you energized

• Discretionary benefit stipend giving people the ability to spend where it matters most

• Free alphorn lessons

These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.

Be You, With Us

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.