Enterprise Sales Director - Majors, Retail

Sierra is the leading platform for customer-facing AI agents, working with major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is primarily in-person based in San Francisco, with growing offices across North America, Europe, and Asia. Co-founded by Bret Taylor and Clay Bavor.

Sierra partners with a large and growing number of retailers across apparel, beauty, grocery, big-box, home, auto, consumer services, marketplaces, and consumer technology. Their AI agents help millions of shoppers daily with order tracking, returns, product discovery, and support, and also drive revenue through personalized recommendations, cart recovery, win-back campaigns, and in-store support.

• Independently drive complex enterprise deals end-to-end, managing 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, and earn credibility quickly with new stakeholders.
• Manage deal risk proactively: identify and manage risk early; build rigorous stakeholder maps for accounts.
• Make hard calls on pricing, escalation timing, exec alignment, and deal strategy, coming with a point of view.
• Leverage leadership and co-founders for exec engagement when it moves a deal.
• Act as a visible, steady leader on deal teams; proactively elevate the team's standard.
• Operate as an AI-native seller: leverage AI tools across the sales cycle—account research, personalized outreach, call summarization, pipeline forecasting, and deal execution—to automate low-value tasks and reinvest time in high-value relationships.

• 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—analyze market trends, spot opportunities, and make data-driven decisions.
• Familiarity with the AI landscape, key players, and emerging trends (preferred).

Salary range: $315,000 - $355,000 USD per year, plus equity and commission. Benefits for full-time employees include 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 and snacks, and a discretionary benefit stipend.

Apply via the provided application link.