Enterprise Sales Director - Strategic

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.