About this role.
Sierra is seeking a senior Enterprise Sales Leader to recruit, coach, and lead an enterprise account executive team across a region. The leader will own regional revenue performance, forecasting, pipeline quality, and execution of the sales process. They will be directly involved in complex customer pursuits, including pricing, negotiations, and close strategy for large enterprise opportunities. The role requires 10–15+ years of enterprise sales experience, at least five years of people leadership, and demonstrated success managing $1M+ complex deals. Familiarity with AI, early-stage go-to-market development, and data-driven operating discipline are strong differentiators.
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 establish clear stage definitions, inspect pipeline quality in structured weekly reviews, and tie forecast calls to verified customer actions rather than rep sentiment. I also use conversion, aging, coverage, and close-plan data to identify risk early and coach managers and sellers on corrective actions.
I start by validating the business problem, stakeholder map, decision process, and compelling event. From there, I help the AE build a mutual action plan, align executive sponsors, quantify value, address technical and commercial risks, and maintain a clear close strategy through negotiation.
I would hire for enterprise rigor, curiosity, consultative selling ability, and comfort operating in ambiguity. I would pair a repeatable onboarding program with clear operating cadences, deal reviews, customer learning loops, and coaching that helps the team translate an evolving AI product into measurable business outcomes.
I would monitor quota attainment, forecast accuracy, pipeline coverage, stage conversion, sales-cycle length, deal aging, win rate, average contract value, and new pipeline creation. I would segment these metrics by seller, segment, source, and deal type to separate execution issues from market or product gaps.
I set explicit engagement criteria for leadership involvement, such as strategic accounts, late-stage risk, executive alignment, or complex commercial terms. In each engagement, I clarify ownership, coach rather than take over, and use the opportunity to strengthen the seller’s judgment and repeatability for future deals.
About us
At Sierra, we’re building a platform to enable every company in the world to build better, more human customer experiences with AI. We partner with industry leaders such as SoftBank, Uber, Rivian, CLEAR, and Sutter Health. 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 Family. 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 your region, 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: Extensive experience in 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: You’ve run and managed end-to-end complex deals ($1M+).
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, as well as fluency with AI tooling and workflows.
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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