[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 – Majors, 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[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 315k–325k / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished26 Oct 2026Apply before25 Nov 2026Listing views47Application actions4Application 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 lead major retail enterprise opportunities for its customer-facing AI agent platform. The role owns complex end-to-end sales cycles, including prospecting, executive engagement, stakeholder mapping, pricing strategy, and closing six- and seven-figure deals. Success requires 8–10 years of enterprise sales experience, a record of managing $1M+ quotas, and the ability to build trusted C-suite relationships. This is a highly autonomous, high-intensity sales position that emphasizes AI-enabled selling and strategic deal leadership. ## 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 insightThe role requires independently closing complex, high-value enterprise deals with senior retail stakeholders and navigating pricing, risk, and executive escalation decisions. Expectations for quota ownership, multi-threading, and AI-native execution make it a senior, demanding sales role. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$320,000US market range (per year)$250k–$375k0$412.50k AI insightThe employer discloses an annual USD compensation range of $315,000–$325,000, with a midpoint of $320,000. Estimated US annual market compensation for a senior enterprise sales director selling AI software into major retail accounts is approximately $250,000–$375,000; actual earnings may vary based on base/variable-pay structure, quota attainment, territory, and equity. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise sales](https://jobicy.com/jobs?search_keywords=Enterprise%20sales.md)[Retail technology sales](https://jobicy.com/jobs?search_keywords=Retail%20technology%20sales.md)[Complex deal management](https://jobicy.com/jobs?search_keywords=Complex%20deal%20management.md)[C-suite relationship building](https://jobicy.com/jobs?search_keywords=C-suite%20relationship%20building.md)[Account strategy](https://jobicy.com/jobs?search_keywords=Account%20strategy.md)[Stakeholder mapping](https://jobicy.com/jobs?search_keywords=Stakeholder%20mapping.md)[Pipeline forecasting](https://jobicy.com/jobs?search_keywords=Pipeline%20forecasting.md)[Sales prospecting](https://jobicy.com/jobs?search_keywords=Sales%20prospecting.md)[Negotiation](https://jobicy.com/jobs?search_keywords=Negotiation.md)[Pricing strategy](https://jobicy.com/jobs?search_keywords=Pricing%20strategy.md)[Risk management](https://jobicy.com/jobs?search_keywords=Risk%20management.md)[AI sales tools](https://jobicy.com/jobs?search_keywords=AI%20sales%20tools.md)[Market analysis](https://jobicy.com/jobs?search_keywords=Market%20analysis.md)[Executive communication](https://jobicy.com/jobs?search_keywords=Executive%20communication.md) Sample interview questionsDescribe a six- or seven-figure enterprise deal you led from initial outreach to close.I would explain the customer’s business problem, buying committee, deal timeline, and my account plan. I would highlight how I created executive alignment, addressed risk early, coordinated internal resources, and quantified the resulting business value to secure the close. How do you build and maintain relationships across a C-suite buying committee? I map each executive’s priorities, influence, and potential concerns early in the cycle. I tailor the business case to their outcomes, maintain a consistent cadence of value-based communication, and use executive sponsors only when they can advance a specific decision. How would you position customer-facing AI agents to a large retailer? I would start with the retailer’s customer-experience and revenue objectives, then connect AI agents to practical outcomes such as faster issue resolution, better product discovery, increased conversion, cart recovery, and scalable support. I would validate the opportunity through measurable use cases and a clear implementation path. What is your approach to identifying and mitigating deal risk? I use stakeholder maps, mutual action plans, qualification criteria, and regular deal reviews to identify gaps in sponsorship, budget, technical validation, procurement, or competitive positioning. I assign owners and deadlines to each risk and escalate with a recommended path forward rather than simply reporting the problem. How do you use AI tools to improve enterprise sales execution? I use AI to accelerate account research, personalize outreach, summarize calls, identify follow-up actions, and improve forecast quality. The time saved is reinvested in customer discovery, executive relationship building, and strategic deal planning rather than replacing high-value human engagement. 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 * Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close. * Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders. * Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts. * Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem. * Leverage leadership & co-founders: Bring in Sierra’s co-founders effectively for exec engagement when it moves a deal. * Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team’s standard without being asked. * 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 * 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts. * Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. * Proven ability to multi-thread and build trusted relationships across customer C-suites. * Exceptional verbal and written communication. * Analytical mindset – you analyze market trends, spot opportunities, and make data-driven decisions. ### Even better… * 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. Show more [Apply now >](https://jobicy.com/jobs/157236-enterprise-sales-director-majors-retail.md) * ![Upload CV](data:image/svg+xml;base64,PHN2ZyB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciIHdpZHRoPSI2NSIgaGVpZ2h0PSI2NSIgZmlsbD0ibm9uZSIgeG1sbnM6dj0iaHR0cHM6Ly92ZWN0YS5pby9uYW5vIj48ZyBjbGlwLXBhdGg9InVybCgjQSkiPjxwYXRoIGQ9Ik0wIDBINjVWNjVIMFYwWiIgZmlsbD0iIzAyOWFlYiIvPjxnIGZpbGw9IiNmZmYiIHN0cm9rZT0iI2ZmZiIgc3Ryb2tlLXdpZHRoPSIyIj48cGF0aCBkPSJNMzMuMDQ5IDE1LjQ1NGExLjQzIDEuNDMgMCAwIDAtMi4wOTcgMGwtNy41NzkgOC4xNDdhMS4zOCAxLjM4IDAgMCAwIC4wOSAxLjk3MyAxLjQ0IDEuNDQgMCAwIDAgMi4wMDgtLjA4OGw1LjEwOS01LjQ5MnYyMC42MWExLjQxIDEuNDEgMCAwIDAgMS40MjEgMS4zOTdjLjc4NSAwIDEuNDIxLS42MjUgMS40MjEtMS4zOTd2LTIwLjYxbDUuMTA5IDUuNDkyYTEuNDQgMS40NCAwIDAgMCAyLjAwOC4wODggMS4zOCAxLjM4IDAgMCAwIC4wOS0xLjk3M2wtNy41NzktOC4xNDZ6TTE2Ljc2OSAzOC40YzAtLjc3My0uNjItMS40LTEuMzg1LTEuNFMxNCAzNy42MjcgMTQgMzguNHYuMTAybC4yMTUgNi4yMjljLjIyMyAxLjY4LjcwMSAzLjA5NSAxLjgxMyA0LjIxOHMyLjUxIDEuNjA3IDQuMTcyIDEuODMzYzEuNi4yMTggMy42MzYuMjE4IDYuMTYuMjE4aDExLjI4bDYuMTYtLjIxOGMxLjY2Mi0uMjI2IDMuMDYxLS43MDkgNC4xNzItMS44MzNzMS41ODktMi41MzggMS44MTMtNC4yMThDNTAgNDMuMTEzIDUwIDQxLjA1NSA1MCAzOC41MDNWMzguNGMwLS43NzMtLjYyLTEuNC0xLjM4NS0xLjRzLTEuMzg1LjYyNy0xLjM4NSAxLjRsLS4xOSA1Ljk1OGMtLjE4MiAxLjM3LS41MTUgMi4wOTUtMS4wMjYgMi42MTJzLTEuMjI4Ljg1My0yLjU4MyAxLjAzOGMtMS4zOTUuMTktMy4yNDMuMTkzLTUuODkzLjE5M0gyNi40NjJjLTIuNjUgMC00LjQ5OC0uMDAzLTUuODkzLS4xOTMtMS4zNTUtLjE4NC0yLjA3Mi0uNTIxLTIuNTgzLTEuMDM4cy0uODQ0LTEuMjQyLTEuMDI2LTIuNjEyYy0uMTg3LTEuNDEtLjE5MS0zLjI3OS0uMTkxLTUuOTU4eiIvPjwvZz48L2c+PGRlZnM+PGNsaXBQYXRoIGlkPSJBIj48cGF0aCBmaWxsPSIjZmZmIiBkPSJNMCAwaDY1djY1SDB6Ii8+PC9jbGlwUGF0aD48L2RlZnM+PC9zdmc+) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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