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Sierra is building an AI platform to help businesses create better, more human customer experiences. The company was founded by Bret Taylor (former Salesforce co-CEO, Facebook CTO, Google Maps co-creator) and Clay Bavor (18-year Google veteran who led Google Labs, AR/VR, and Google Workspace). Sierra is headquartered in San Francisco with offices across Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
As Enterprise Sales Director, you will architect Sierra's most complex, multi-business-unit, multi-geography deals. You'll operate as a trusted advisor to customer C-suites, managing sophisticated deal structures and risk with precision. You'll regularly engage Sierra's co-founders in front of strategic customers, pitching with founder-level conviction and expertise. Your role is to shape how Sierra approaches its most important accounts and set the standard for the broader sales organization.
You'll leverage AI tools across the entire 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. You'll continuously adopt and experiment with new tools to work faster and smarter than traditional methods allow.
Required: 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 $1M+ quotas and running end-to-end complex 6- and 7-figure ACV deals. Deep, sustained C-suite relationships with the gravitas to be treated as a peer by executive buyers. Mastery of complex deal structuring, risk navigation, and pricing. Exceptional executive communication with a reputation for precision and trust.
Preferred: Deep familiarity with the AI landscape and ability to speak credibly to technical and business stakeholders. Experience operating alongside founders/executives in front of strategic customers. Experience building GTM strategies, building sales teams, or scaling sales motions from early stage.
