Suggested rewrite: Led a cross-functional initiative that improved [business outcome] by [measurable result], demonstrating experience relevant to this role...
Enterprise Sales Leader, Consumer Business Services
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The role, at a glance.
Sierra is seeking an Enterprise Sales Leader to lead and grow a regional enterprise account-executive organization serving consumer business services industries. The leader owns regional revenue performance, forecast accuracy, pipeline quality, strategic deal execution, pricing, and negotiation support. Candidates need 10–15+ years of enterprise sales experience, at least five years of people leadership, and a record of closing complex $1M+ enterprise deals. The role requires strong executive communication, data-driven operating discipline, AI-market familiarity, and the ability to build scalable go-to-market motions.
Role DNA
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Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I establish clear stage-entry and exit criteria, inspect pipeline quality in regular operating reviews, and use leading indicators such as stakeholder coverage, validated business impact, and next-step quality. I pair this discipline with coaching so forecasts become a management tool rather than a reporting exercise.
I would first diagnose the cause of the stall by mapping the buying committee, decision process, value case, competition, and commercial blockers. I would then help create an executive engagement plan, clarify mutual action steps, align pricing and negotiation strategy, and ensure the customer has a compelling path to a decision.
I hire for consultative selling ability, executive presence, curiosity, operating rigor, and evidence of managing complex cycles. Once hired, I use structured onboarding, deal reviews, call coaching, measurable performance expectations, and individualized development plans to build both performance and future leadership capability.
I would begin with market segmentation, ideal-customer-profile definition, priority use cases, and evidence of measurable customer outcomes. I would translate those insights into account prioritization, messaging, sales plays, partner alignment, and feedback loops with product and marketing, then measure conversion and sales-cycle signals to refine the motion.
I set transparent expectations around activity quality, pipeline health, forecast integrity, and outcomes, while making coaching and peer learning routine. Teams perform best when leaders address gaps directly, remove obstacles quickly, share lessons from wins and losses, and maintain respect for individuals throughout.
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 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.
About the Consumer Business Services team
Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.
This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.
Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.
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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