Enterprise Sales Director, Retail

About us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor and Clay Bavor who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. 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 Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. Manage relationships : Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations. Negotiating & closing complex deal cycles : Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders. Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations. Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. 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 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. Strong communication skills: Exceptional verbal and written communication abilities. Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. Prospecti