Enterprise Sales Director - Majors, Retail

About us

At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.

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 Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.

Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs.

Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

• 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.

• Independently 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.

• 8- 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,…