Enterprise Sales Director - Strategic, Retail

Sierra

1d • CA$375,000 - CA$430,000 • Onsite

About The Position

Sierra is seeking an Enterprise Sales Director with a strategic focus on the Retail sector. This role involves architecting complex deals, building C-suite relationships, and leveraging AI tools to drive sales. The position is based in San Francisco but the company has a global presence. Sierra is dedicated to creating AI-powered platforms for enhanced customer experiences and is partnering with a wide range of retailers to redefine customer engagement and revenue generation through AI agents.

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.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed