Enterprise Sales Director - Majors, Retail

Retail Team OpportunitySierra 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 DoIndependently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.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 Bring8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.Proven ability to multi-thread and build trusted relationships across customer C-suites.Exceptional verbal and written communication.Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.Even Better...Familiarity with the AI landscape, key players, and emerging trends.Our ValuesTrust: 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 OfferWe want our benefits to reflect our values and offer the following to full-time employees:Flexible (unlimited) paid time offMedical, dental, and vision benefits for you and your familyLife insurance and disability benefitsRetirement plan dependent on country of employmentParental leaveFertility and family building benefits through CarrotLunch, as well as delicious snacks and coffee to keep you energizedDiscretionary benefit stipend giving people the ability to spend where it matters mostFree alphorn lessonsThese 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 UsWe'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.