About us

• At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Singapore, and Japan.

• 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 financial services team

• Financial Services is one of Sierra’s fastest-growing industries. Our customers are systemically important banks, neobanks committed to building more delightful banking software, insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.

• Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.

• Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.

What you’ll do

As part of Sierra’s Financial Services team, you will own end-to-end enterprise AI deployments for some of the most sophisticated financial institutions in the world. You will partner directly with senior executives to define their AI strategy, translate it into executable programs, and drive high-visibility deployments that handle millions of real customer conversations per year.

• Serve as a strategic thought partner to C-suite and senior executives, shaping enterprise AI roadmaps and informing high-stakes transformation initiatives. Lead executive steering forums and decision-making processes, including preparation of strategic narratives and performance reporting.

• Own multi-workstream, cross-functional programs from strategy through production deployment, driving alignment across technical, operational, compliance, and executive stakeholders.

• Build durable executive relationships and lead high-stakes discussions around AI risk, compliance, operational redesign, and customer experience transformation.

• Translate strategic objectives into production-grade AI systems — partnering closely with engineering and product to design, test, and iterate on agents deployed at enterprise scale.

• Structure ambiguous business challenges into clear workstreams, define success metrics, and drive disciplined execution against measurable outcomes.

• Contribute data-driven, strategic insights to customers’ and internal decisions.

• Translate Financial Services’ unique challenges into scalable AI solutions and contributions to the Sierra’s Financial Services roadmap.

What you’ll bring

We’re particularly excited about candidates who have led complex, enterprise-facing engagements and are eager to move from advising on strategy to owning its execution.

• Demonstrated experience owning complex projects and executive-level customer relationships. Example successful candidates include:

  • Engagement Managers from leading management consulting firms

  • Product Managers who have interfaced with customers when developing and launching new products or features, especially those involving many streams of effort.

  • Former founders that have built and scaled products and teams.

• Experience interfacing with executives at the VP level and above - the ability to speak with both confidence and accuracy about complex or high-emotion topics.

• High EQ - the ability to motivate a team, and the wisdom to interface with external and internal stakeholders who may at times disagree.

• Humility - seeking feedback, the ability to prioritize learning over ego, and recognition that great teams and products are built through continuous improvement.

• Mastery of program ownership best practices and demonstrated ability to drive large deliverables on-time and at enterprise quality and scale.

• Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.

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 (e.g., 401K, pension) with Sierra match

• 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.

Compensation Range: $140K - $280K