Enterprise Sales Director
Sierra
Enterprise Sales Director
Sierra
Builds AI agents for customer conversations
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.
Sierra was co-founded by Bret Taylor and Clay Bavor who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
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.
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
Lunch, as well as delicious snacks and coffee to keep you energized when working onsite
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 employment type, 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.
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 through the link on this page even if your experience doesn't precisely match the job description.
Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at [email protected]. Requests are handled confidentially and do not affect your candidacy.
We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.
Sierra builds AI agents that handle customer conversations for businesses, from answering support questions to guiding purchases and managing account requests. Companies deploy the same agent across voice, chat, email, and messaging channels, with behavior shaped by their brand guidelines and business policies. Its Ghostwriter tool creates and updates agents from plain instructions or existing company materials, then tests changes before teams approve them. The platform connects agents to business systems so they take action, and Sierra charges for completed outcomes rather than the AI tokens consumed. Sierra was founded in 2023 and is headquartered in San Francisco, California, United States.
Explore more opportunities at Sierra