GTM Operations - Pricing

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.

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.

What You'll Do

Sierra’s outcomes-based pricing model is central to how we partner with customers. In this role, you will work with senior leaders across Sales, Operations, Product, Finance, and Legal. You will help negotiate complex partnerships with Fortune 500 companies, build business cases that demonstrate Sierra’s value, and shape pricing strategies for AI agents that drive revenue, improve retention, and transform core business processes.

• Lead pricing strategy for major enterprise opportunities, from early customer discussions through negotiation and close

• Develop commercial models and ROI analyses that connect Sierra’s performance to measurable customer value

• Bring clear analysis and sound judgment to high-stakes customer negotiations

• Partner across the company to turn new product capabilities into scalable commercial offerings

What You'll Bring:

• 4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.

• Experience negotiating complex customer partnerships and familiarity with navigating sales cycles

• Strong financial modeling skills and the ability to turn analysis into a clear executive recommendation

• Excellent commercial judgment, including the ability to make thoughtful decisions with incomplete information

• Clear written and verbal communication with senior leaders

• Degree in Business Administration, Finance, or related field, or equivalent professional experience

Even better...

• Experience in partnerships, business development, and value engineering roles

• Familiarity with AI or conversational AI technologies

• Previous 0-1 startup or fast-paced high-growth environment experience

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

• 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.

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 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.