Enterprise Sales Director - Strategic
About The Position
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.
Requirements
- 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.
Nice To Haves
- 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.
Responsibilities
- 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.
Benefits
- 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, as well as delicious snacks and coffee to keep you energized
- Discretionary benefit stipend giving people the ability to spend where it matters most
- Free alphorn lessons
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
