[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 – Strategic 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 420k–445k / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished2 Nov 2026Apply before2 Dec 2026Listing views24Application actions2Application 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 a senior enterprise sales leader to own its largest and most complex strategic opportunities. The role centers on structuring multi-business-unit, multi-geography deals, developing trusted C-suite relationships, and managing risk, pricing, and executive-level sales motions. The successful candidate will work closely with Sierra’s founders and influence account strategy and standards for the broader sales organization. This is a high-impact, quota-carrying role for an experienced seller with a record of closing six- and seven-figure ACV deals and using AI tools throughout the sales cycle. ## 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 role requires ownership of multi-million-dollar strategic deals involving executive stakeholders, sophisticated commercial structures, and significant deal risk. Success depends on exceptional judgment, executive credibility, and the ability to operate independently in high-stakes situations. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Highly competitiveC$432,500CA market range (per year)C$280k–C$450k0C$495.00k AI insightThe employer discloses a yearly compensation range of CAD 420,000–445,000, with a midpoint of CAD 432,500. This is a credible high-end range for a Canadian strategic enterprise sales director responsible for complex, multi-million-dollar opportunities; the estimated Canadian market range is CAD 280,000–450,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise Sales](https://jobicy.com/jobs?search_keywords=Enterprise%20Sales.md)[Strategic Account Management](https://jobicy.com/jobs?search_keywords=Strategic%20Account%20Management.md)[Complex Deal Structuring](https://jobicy.com/jobs?search_keywords=Complex%20Deal%20Structuring.md)[C-Suite Relationship Management](https://jobicy.com/jobs?search_keywords=C-Suite%20Relationship%20Management.md)[Sales Negotiation](https://jobicy.com/jobs?search_keywords=Sales%20Negotiation.md)[Pricing Strategy](https://jobicy.com/jobs?search_keywords=Pricing%20Strategy.md)[Pipeline Forecasting](https://jobicy.com/jobs?search_keywords=Pipeline%20Forecasting.md)[Account Planning](https://jobicy.com/jobs?search_keywords=Account%20Planning.md)[Go-to-Market Strategy](https://jobicy.com/jobs?search_keywords=Go-to-Market%20Strategy.md)[Multi-Stakeholder Selling](https://jobicy.com/jobs?search_keywords=Multi-Stakeholder%20Selling.md)[Sales Quota Management](https://jobicy.com/jobs?search_keywords=Sales%20Quota%20Management.md)[AI Sales Tools](https://jobicy.com/jobs?search_keywords=AI%20Sales%20Tools.md)[Executive Communication](https://jobicy.com/jobs?search_keywords=Executive%20Communication.md) Sample interview questionsDescribe a complex multi-million-dollar deal you led from initial engagement to close.I would explain the customer’s business objectives, stakeholder map, commercial complexity, competitive landscape, and the specific actions I took to create alignment. I would quantify the ACV, sales-cycle length, outcome, and lessons applied to future strategic opportunities. How do you build credibility with C-suite buyers while maintaining momentum across working teams? I begin with the executive’s strategic priorities and connect the solution to measurable business outcomes. In parallel, I establish a clear operating cadence with technical, procurement, legal, and business stakeholders so executive alignment is supported by detailed execution. How would you approach structuring a strategic AI platform deal involving several business units and geographies? I would map the decision process, value drivers, deployment dependencies, data and security requirements, and regional commercial constraints. I would then build a phased proposal with clear success metrics, governance, pricing logic, and executive sponsorship to manage risk while preserving expansion potential. What is your approach to managing deal risk late in an enterprise sales cycle? I identify risks early through stakeholder mapping, mutual action plans, qualification discipline, and direct validation of procurement, security, legal, and budget requirements. If risk emerges late, I escalate transparently, realign on customer value, and create specific owners and dates for each blocker. How do you use AI tools to improve enterprise sales execution without losing the personal nature of strategic selling? I use AI to accelerate research, summarize calls, identify account signals, improve follow-up preparation, and support forecasting. I reserve the time saved for high-value activities such as executive discovery, relationship building, tailored value articulation, and thoughtful negotiation. 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. ### 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 operating alongside founders/executives in front of strategic customers. * Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. ### 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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