Enterprise Sales Director, Benelux

Job4Travelers; Milwaukee (WI); Presencial; USD 120.000 - 200.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Discretionary benefit stipend

30% tax ruling eligibility

Benelux base flexibility

Descripción de la vacante

Sierra is seeking an experienced Enterprise Sales professional to lead the Benelux region from the ground up, working in-person with enterprise clients across the Benelux market. You will manage complex deals, build executive relationships, and shape the regional GTM motion in a fast-paced environment.

Fluency in Dutch and English is required, along with a track record of exceeding quotas. This role is based in the Benelux region with a strong emphasis on on-site client engagement and

Formación

• 10+ years in enterprise customer-facing sales
• Experience managing $1M+ quotas
• Strong communication with C-level stakeholders

Responsabilidades

• Prospecting & Lead Generation to build enterprise relationships
• Manage Relationships with key decision-makers at largest customers
• Negotiate & close complex deals
• Develop Sales Strategy & Planning to hit targets
• Help Define Our Sales Motion as the first regional salesperson
• Collaborate Cross-Functionally with GTM, product, and ops teams

Conocimientos

Enterprise sales

Dutch language

English language

Quota management

Descripción del empleo

This role is explicitly described as part of an in-person company culture — Sierra emphasizes being "primarily an in-person company." While the position is based in the Benelux region (Netherlands/Belgium/Luxembourg) rather than San Francisco HQ, the nature of enterprise sales — building relationships with key decision-makers, attending client meetings, and navigating complex deal cycles — strongly implies significant in-person presence.

For digital nomads, this role is not suitable for a location-independent lifestyle. As the first salesperson in region, you'll be expected to be physically present in the Benelux market, meeting enterprise clients and building relationships on the ground. Fixed business-hour availability in the CET/CEST timezone (UTC+1/+2) is effectively required.

That said, there are a few noteworthy points for location-aware professionals:

• The discretionary benefit stipend could cover coworking memberships in Amsterdam, Brussels, or Luxembourg City.
• The Netherlands offers a 30% tax ruling for qualifying international knowledge workers, which could significantly boost net take-home pay.
• The role does not list a specific city, so candidates with flexibility within the Benelux region may have some choice of base.

If you're seeking a truly remote or nomadic-friendly enterprise sales role in AI, look instead for roles explicitly labeled "remote-first" with async sales processes and no regional office anchor.

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.

Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce and CTO of Facebook, and was one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, most recently leading Google Labs, and also started Google's AR/VR effort, Project Starline, and Google Lens.

What You'll Do

• Prospecting & Lead Generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
• Manage Relationships: Build and maintain strong relationships with key decision-makers and stakeholders at 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 targets. Craft tailored sales presentations and proposals that meet enterprise customer needs. Collaborate with marketing to implement effective sales campaigns.
• Help Define Our Sales Motion: You'll be the first salesperson in region — 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 product, technical, and operations teams 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 through 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 professionally and personally.

Customer Obsession: We deeply understand our customers' business goals and relentlessly focus on driving outcomes, not just technical milestones. When our customer has 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. We are proud of the products we produce and continuously self-reflect to improve.

Intensity: We know we don't have the luxury of patience. We play to win. 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. We are the best technology company for parents. We support and respect each other and celebrate 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 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. It is important to us that the diversity of our employees represents the diversity of our customers. 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.

Is this role fully remote or office-based? Sierra describes itself as "primarily an in-person company," so while the role is based in the Benelux region rather than HQ in San Francisco, significant in-person client and team engagement is expected. This is not a fully remote position. What language skills are required for this role? Professional fluency in both Dutch and English is required, reflecting the Benelux market focus. What quota size is expected for this position? Sierra requires candidates to have experience managing a $1M+ quota, with a track record of running end-to-end complex enterprise deals. Will I be working alone in the region, or is there a team? You will be the first salesperson in the Benelux region, which means you'll be defining the regional sales motion. You'll collaborate cross-functionally with Sierra's broader GTM, product, and operations teams globally. Does Sierra offer equity to employees? Yes, eligible full-time employees can participate in Sierra's equity plans, subject to the terms of the applicable plans and policies.

Helping travelers find remote work and build location-independent careers around the world.