Enterprise Sales Director - Strategic

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

• Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.

• Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.

• Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.

• Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.

• Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.

• 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

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.

• Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.

• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.

• Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.

• Mastery of complex deal structuring, risk navigation, and pricing.

• Exceptional executive communication and a reputation for precision and trust.

Even better...

• Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.

• Experience operating alongside founders/executives in front of strategic customers.

• Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.

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