Enterprise Sales Director - Majors

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.

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.

What you'll do

• 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.

What you'll bring

• 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, and make data-driven decisions.

Even better...

• Familiarity with the AI landscape, key players, and emerging trends.

Our values

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