SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Sierra is building an AI platform that helps businesses create better, more human customer experiences. The company is 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 operates primarily from San Francisco with offices across Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
The Retail team partners with major retailers across apparel, beauty, grocery, big-box, home, auto, consumer services, and marketplaces. Sierra's AI agents serve millions of shoppers daily—handling order tracking, returns, product discovery, and customer service. Beyond support, the platform drives revenue through personalized recommendations, cart recovery, win-back campaigns, and in-store support that converts unanswered calls into visits and sales.
As Enterprise Sales Director for Retail, you will architect Sierra's most complex, multi-business-unit, multi-geography deals. You'll hold trusted relationships across customer C-suites and working teams, regularly engaging Sierra's co-founders in strategic customer conversations. You'll operate with precision in messaging, positioning, and timing, shaping how Sierra approaches its most important accounts and setting standards for the broader sales organization.
You'll 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 time into high-value customer relationships. This is a role for an AI-native seller who continuously adopts new tools to work faster and smarter than traditional methods allow.
You bring 10–12+ years of enterprise and strategic sales experience owning the largest, most complex accounts. You've closed multi-million-dollar, multi-stakeholder deals spanning business units and geographies, managed $1M+ quotas, and run end-to-end complex 6- and 7-figure ACV deals. You have deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers. You master complex deal structuring, risk navigation, and pricing, with exceptional executive communication and a reputation for precision and trust.
Ideal candidates have deep familiarity with the AI landscape and can speak credibly to both technical and business stakeholders. Experience operating alongside founders and executives in front of strategic customers is a strong plus.
