# Enterprise Sales Director - Strategic, Retail at Sierra

Sierra is hiring an Enterprise Sales Director - Strategic, Retail for a remote role open to applicants in Canada. It pays CAD 375k-CAD 430k a year and Level rates it Little AI ●○○○; you can [apply on Sierra](https://jobsbylevel.com/go/3184fd07-c556-4740-b056-ae8b9e2ccbbe?utm_medium=ai-agent).

AI Level 1, AI centrality 20 out of 100. Remote (Canada - Remote).

## Details

- Company: [Sierra](https://jobsbylevel.com/companies/sierra)
- AI level: AI Level 1 (score 20 out of 100)
- Location: Remote (Canada - Remote)
- Salary: CAD 375k-CAD 430k
- Posted: August 5, 2026
- Apply: https://jobsbylevel.com/go/3184fd07-c556-4740-b056-ae8b9e2ccbbe?utm_medium=ai-agent
- Free CV review for this job: https://jobsbylevel.com/cv-review?job=enterprise-sales-director-strategic-retail-at-sierra-5ce227

## Prepare for this job

The job page lists 5 likely interview questions for this offer, with a CV checklist: https://jobsbylevel.com/jobs/enterprise-sales-director-strategic-retail-at-sierra-5ce227

## Description

About us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. About the Retail team Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. 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

The description is cut here. Read the full offer: https://jobsbylevel.com/jobs/enterprise-sales-director-strategic-retail-at-sierra-5ce227

Source: https://jobsbylevel.com/jobs/enterprise-sales-director-strategic-retail-at-sierra-5ce227

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