About this role.
Sierra is hiring a Regional VP, Sales to lead and scale an enterprise account-executive team across Spain. The leader will own regional quota attainment, forecasting, pipeline quality, and sales-process execution while partnering with RevOps. They will also participate directly in strategic customer conversations, complex buying committees, pricing, negotiations, and close plans. The role calls for 10–15+ years in enterprise sales, at least five years of people leadership, and experience managing large, end-to-end deals. Success depends on disciplined operating cadence, executive-level communication, data-driven decision-making, and familiarity with the AI market.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would define consistent stage-exit criteria, inspect opportunity evidence rather than rep optimism, and review coverage, conversion, deal slippage, and next-step quality weekly. I would use that operating rhythm to identify risks early, coach to specific gaps, and create a forecast that leadership can trust.
I start by mapping every stakeholder's influence, priorities, risks, and decision role. Then I help the AE build a mutual action plan, quantify the business case, create executive alignment, and address procurement, security, and legal issues before they become late-stage blockers.
I would hire for enterprise rigor, curiosity, customer empathy, and the ability to navigate ambiguity—not only prior quota attainment. Once hired, I would provide structured onboarding, regular deal coaching, clear performance standards, and development plans that identify future leaders.
I engage where executive sponsorship, deal strategy, or internal escalation can materially change an outcome, while ensuring the AE remains the clear deal owner. After each engagement, I debrief the approach so the rep gains repeatable skills rather than becoming dependent on leadership intervention.
I would lead with measurable customer and business outcomes, then connect the solution to the buyer's operational priorities and customer experience goals. I would proactively address trust, safety, implementation, governance, and change-management concerns with the right technical and executive stakeholders involved early.
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 and Clay Bavor. 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
Lead & develop a high-performing sales team – Hire, onboard, and develop AEs across Spain. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team
Own regional performance – Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights
Be deeply involved in deals – Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy
What you’ll bring
10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.
People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.
Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Strong Communication Skills: Exceptional verbal and written communication abilities.
Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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