[All remote jobs](https://jobicy.com/jobs.md)[![Sierra logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/9877fe33-221.jpeg)](https://jobicy.com/company/sierra.md)[Sierra](https://jobicy.com/company/sierra.md) # Enterprise Sales Director, Retail Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/sierra.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 325k–365k / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished2 Nov 2026Apply before2 Dec 2026Listing views45Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Sierra is seeking an Enterprise Sales Director to grow strategic retail accounts for its customer-facing AI agent platform. The role owns enterprise prospecting, executive relationship management, sales strategy, negotiations, and closing complex six- and seven-figure ACV opportunities. It requires 6–8 years of enterprise customer-facing sales experience, including ownership of a CA$1M+ quota and end-to-end deal execution. The successful candidate will work closely with GTM, product, technical, operations, legal, and finance teams while using AI tools throughout the sales cycle. This is a remote Canada-based full-time position focused on retail, consumer brands, and measurable revenue outcomes. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior enterprise sales role involving high-value, multi-stakeholder deal cycles, strategic account development, and quota ownership. Success depends on independently creating pipeline, navigating procurement and legal negotiations, and articulating an emerging AI product's business value to retail executives. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Highly competitiveC$345,000CA market range (per year)C$220k–C$360k0C$396.00k AI insightThe employer discloses a yearly compensation range of CA$325,000–CA$365,000, with a midpoint of CA$345,000. This is a credible upper-market range for a senior Canadian enterprise sales director role with responsibility for large, complex retail accounts; variable compensation structure is not specified. The estimated Canadian market range for comparable enterprise sales leadership roles is CA$220,000–CA$360,000 yearly. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise sales](https://jobicy.com/jobs?search_keywords=Enterprise%20sales.md)[Retail technology](https://jobicy.com/jobs?search_keywords=Retail%20technology.md)[Strategic account management](https://jobicy.com/jobs?search_keywords=Strategic%20account%20management.md)[Lead generation](https://jobicy.com/jobs?search_keywords=Lead%20generation.md)[Cold calling](https://jobicy.com/jobs?search_keywords=Cold%20calling.md)[Sales strategy](https://jobicy.com/jobs?search_keywords=Sales%20strategy.md)[Complex deal negotiation](https://jobicy.com/jobs?search_keywords=Complex%20deal%20negotiation.md)[Pipeline management](https://jobicy.com/jobs?search_keywords=Pipeline%20management.md)[Executive stakeholder management](https://jobicy.com/jobs?search_keywords=Executive%20stakeholder%20management.md)[Value-based selling](https://jobicy.com/jobs?search_keywords=Value-based%20selling.md)[Sales forecasting](https://jobicy.com/jobs?search_keywords=Sales%20forecasting.md)[AI sales tools](https://jobicy.com/jobs?search_keywords=AI%20sales%20tools.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Market analysis](https://jobicy.com/jobs?search_keywords=Market%20analysis.md)[Contract negotiation](https://jobicy.com/jobs?search_keywords=Contract%20negotiation.md) Sample interview questionsHow have you built and closed a large enterprise opportunity from an initial prospect to a signed agreement?I begin with account research and a clear hypothesis about the customer's business priorities. I map the buying committee, validate pain points through discovery, quantify the expected impact, and develop a mutual action plan that covers technical validation, procurement, legal, and executive sponsorship. I maintain momentum through regular stakeholder alignment and close only after confirming a measurable path to value. How would you position Sierra's AI agents to a major retail brand? I would lead with the retailer's customer and commercial outcomes rather than the technology alone. After identifying priority journeys such as order support, product discovery, cart recovery, or store-call conversion, I would connect Sierra's agents to metrics such as conversion, revenue recovery, service resolution, and customer satisfaction. I would then align product capabilities, implementation requirements, and a phased deployment plan to those outcomes. Describe your approach to navigating a complex procurement and legal process. I engage procurement and legal stakeholders early, understand their risk and approval requirements, and create a realistic close plan with owners and dates. I distinguish between material issues and negotiable preferences, involve internal legal and finance partners promptly, and keep executive sponsors informed of decisions that could affect timing. This approach helps protect the relationship while maintaining commercial discipline. How do you manage a CA$1M+ quota while ensuring healthy pipeline coverage? I segment my territory by strategic fit, potential value, and likelihood to close, then establish clear activity and pipeline-creation targets for each segment. I inspect pipeline quality regularly using stage criteria, stakeholder coverage, next steps, and forecast confidence rather than relying on headline value. I also balance near-term opportunities with deliberate outbound work to maintain sustainable coverage. How do you use AI tools to improve enterprise sales performance without reducing the quality of customer relationships? I use AI to accelerate preparation and administrative work, including account research, call summaries, follow-up drafting, opportunity analysis, and forecast hygiene. I validate outputs before using them and reserve the time saved for deeper customer discovery, executive engagement, and strategic deal work. The goal is to be better informed and more responsive while preserving a thoughtful, human sales process. Opportunity details ## About this role. ### 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](https://www.linkedin.com/in/brettaylor/) and [Clay Bavor](https://www.linkedin.com/in/claybavor/). 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 * Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. * Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations. * Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders. * Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations. * Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. * 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 * 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. * Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. * Strong communication skills: Exceptional verbal and written communication abilities. * Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. * Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling. ### Even better… * Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends. ### Our values * Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. * Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. * Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. * Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. * Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. ### What we offer We want our benefits to reflect our values and offer the following to full-time employees: * 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 These benefits are further detailed in Sierra’s policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra’s equity plans subject to the terms of the applicable plans and policies. ### Be you, with us We’re working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn’t precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. 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