[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, Benelux AI Summary Sierra is seeking an Enterprise Sales Director to establish and grow its enterprise sales motion across the Benelux market. The role owns prospecting, executive relationship management, complex negotiations, and end-to-end closing of strategic AI-platform opportunities. It requires at least 10 years of enterprise sales experience, Dutch and English fluency, and a record of managing complex deals against a €1M+ equivalent quota. As the first sales hire in the region, this person will shape go-to-market strategy while partnering closely with product, technical, legal, finance, and marketing teams. The role is suited to a highly independent seller who can build pipeline and regional market presence from an early-stage foundation.[Apply for this job](#job-application)[View company](https://jobicy.com/company/sierra.md)ShareRemote from[Netherlands](https://jobicy.com/job-region/netherlands.md)SalaryUndisclosedDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished6 Nov 2026Apply before6 Dec 2026Listing views32Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. 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 * 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. * Help define our sales motion: You’ll be the first Sales person in region, and your work will directly impact how our GTM function operates and succeeds in the Benelux. * 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. ### What you’ll bring * 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. * Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in Dutch and English. * Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals. * 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. * 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. Show more [Apply now >](https://jobicy.com/jobs/159416-enterprise-sales-director-benelux.md) > Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## 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, greenfield enterprise-sales role requiring ownership of complex, high-value deal cycles and regional GTM creation. Success depends on executive influence, disciplined pipeline generation, and the ability to navigate multiple internal and customer stakeholders. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$175,000US market range (per year)$145k–$220k0$242.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer base salary is disclosed. The figures are AI-estimated annual USD base-pay benchmarks for a senior enterprise sales director role; commission, equity, and benefits are excluded. ## 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)[Business Development](https://jobicy.com/jobs?search_keywords=Business%20Development.md)[Lead Generation](https://jobicy.com/jobs?search_keywords=Lead%20Generation.md)[Cold Calling](https://jobicy.com/jobs?search_keywords=Cold%20Calling.md)[Complex Deal Negotiation](https://jobicy.com/jobs?search_keywords=Complex%20Deal%20Negotiation.md)[Sales Strategy](https://jobicy.com/jobs?search_keywords=Sales%20Strategy.md)[Go-to-Market Strategy](https://jobicy.com/jobs?search_keywords=Go-to-Market%20Strategy.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)[Sales Presentations](https://jobicy.com/jobs?search_keywords=Sales%20Presentations.md)[AI Industry Knowledge](https://jobicy.com/jobs?search_keywords=AI%20Industry%20Knowledge.md)[Dutch](https://jobicy.com/jobs?search_keywords=Dutch.md)[English](https://jobicy.com/jobs?search_keywords=English.md) Sample interview questionsHow would you build Sierra's enterprise pipeline in the Benelux during your first six months?I would begin by defining priority verticals and ideal customer profiles based on customer-service complexity, digital maturity, and potential AI-agent impact. I would map target accounts and buying committees, combine executive outreach with partner and event channels, and maintain rigorous opportunity qualification. I would review pipeline coverage, stage conversion, and account engagement weekly to refine the approach. Describe your approach to managing a complex enterprise deal with several decision-makers. I establish a mutual action plan early, map economic buyers, champions, technical evaluators, and legal stakeholders, and confirm the business problem each group needs solved. I align measurable success criteria, coordinate internal specialists, and address commercial or security risks before they become late-stage blockers. Regular executive checkpoints keep decisions moving and clarify accountability. What experience do you have selling emerging technology such as AI to enterprise customers? I focus on connecting technology capabilities to a customer's measurable operational and commercial goals rather than leading with product features. For AI solutions, I would address value creation, deployment feasibility, governance, security, and change management with the appropriate stakeholders. I use relevant proof points and a structured pilot-to-production path to build confidence. How do you balance prospecting for new business with managing strategic customer relationships? I protect recurring prospecting time while using account plans and stakeholder cadences to ensure existing opportunities advance. I prioritize activity according to deal value, urgency, fit, and the actions required to remove blockers. A clear CRM discipline allows me to forecast accurately without sacrificing relationship quality. How would you work with product and technical teams when a prospective customer requests capabilities that are not yet available? I would first understand the underlying business requirement and distinguish essential needs from preferred implementation details. I would bring a concise, evidence-based request to internal teams, communicate product realities transparently, and avoid making unapproved commitments. Where appropriate, I would develop a phased solution plan that delivers immediate value while informing product priorities. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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