Enterprise Sales Leader, Consumer Business Services

Sierra; New York (NY); On-site; USD 180,000 - 320,000; Full time

Benefits offered by this job

Flexible PTO

Medical, dental, and vision

Life insurance

Retirement plan

Parental leave

Fertility benefits

Meals & snacks

Discretionary stipend

Alphorn lessons

Job summary

Sierra in San Francisco is seeking a VP of Enterprise Sales to lead our Americas region, building a high-performing team and closing strategic, multi-million deals.

You will guide sales strategy, partner with RevOps, and own forecasts while mentoring senior reps. This role emphasizes collaboration, data-driven decision making, and a deep network in enterprise tech. This position offers the opportunity to shape GTM with AI-powered products.

Qualifications

• 10–15+ years in enterprise customer-facing sales
• People leadership experience (5+ years)
• Experience closing $1M+ deals
• Strong communication skills (verbal & written)

Responsibilities

• Lead and develop a high-performing sales team across your region.
• Own regional performance, forecast accuracy, and pipeline quality.
• Be deeply involved in deals, supporting pricing, negotiations, and closing strategies

Skills

Leadership

Enterprise sales

Forecasting

Communication

Analytical thinking

Job description

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.

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.