Enterprise Sales Director - Strategic, Consumer Business Insights

Sierra

2d•CA$375,000 - CA$430,000•Onsite

About The Position

Sierra partners with businesses that power everyday life for consumers and enterprises, including CPG brands, logistics networks, real estate and facilities teams, and energy and utility providers. The Consumer Business Insights team focuses on bringing AI agents to these essential services to make them faster, more reliable, and more human. This role offers the opportunity to build relationships across a wide range of industries and contribute to technology that impacts daily life. Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. The company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and Family. The co-founders are Bret Taylor and Clay Bavor, both with extensive experience in technology leadership.

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, leading large multi-BU, multi-geo opportunities and designing sophisticated deal structures.
Manage risk with precision and conviction in complex deals.
Operate as part of the customer's team, holding trusted relationships across the customer C-suite and working teams.
Engage at the founder level, regularly engaging and managing Sierra's co-founders in front of customers.
Pitch with co-founder-like conviction and expertise.
Bring precision to messaging, positioning, and timing across every interaction.
Shape strategy for how Sierra approaches its most important accounts.
Set the standard for the broader sales organization.
Operate as an AI-native seller, leveraging AI tools across the full sales cycle for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.
Automate low-value tasks to reinvest time into high-value customer relationships.
Continuously adopt and experiment with new tools to work faster and smarter.