Enterprise Sales Director - Majors

Sierra is the leading platform for customer-facing AI agents, working with major brands like 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.

• 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 risk proactively: identify and manage deal risk early; build rigorous stakeholder maps for accounts.
• Make the hard calls: partner with manager on pricing, escalation timing, exec alignment, and deal strategy.
• Leverage leadership & co-founders 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.
• 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 time into high-value customer 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.
• Even better: familiarity with the AI landscape, key players, and emerging trends.

Salary range: $300K – $345K per year, plus commission and equity. Benefits include flexible (unlimited) paid time off, medical/dental/vision, life insurance and disability benefits, retirement plan, parental leave, fertility and family building benefits, lunch and snacks, discretionary benefit stipend, and free alphorn lessons.

Apply via the provided application link.