Operations Manager, Product & Engineering

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 https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. 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. WHAT YOU’LL DO - Run the operating cadence for Product & Engineering: own planning cycles, roadmap workflows, initiative tracking by region and channel, sequencing, and team initiatives - Design and optimize key processes like product reviews, retrospectives, team syncs, and engineering demos to drive clarity and velocity - Build and maintain operational artifacts such as roadmaps, planning docs, capacity trackers, dashboards, and retros that keep everyone informed and aligned - Coordinate cross-functional initiatives that span Product, Eng, Design, Legal, Sales, and Ops teams—driving alignment, timelines, and accountability - Partner with product, eng and marketing leads to create scalable frameworks for goal-setting (e.g., OKRs), prioritization, and execution - Analyze operational data and team feedback to identify friction points and implement systems that improve execution and outcomes - Build our outbound operations playbook in partnership with Legal and continuously improve it so we can scale with quality and intention WHAT YOU’LL BRING - 6-8+ years of experience in Product Operations, Business Operations, or Program Management in a high-growth, product-led company - Proven track record building and scaling operational processes from scratch - Highly organized and methodical; you bring rigor, structure, and momentum to ambiguous situations - Excellent written and verbal communicator—clear, succinct, and persuasive across stakeholders and levels - Experience partnering closely with Legal, Product, and Engineering, including third-party vendors - Comfortable using tools like Linear, Figma, Google Drive, or similar to create systems that stick - Strong analytical instincts with proficiency in Excel/Sheets; SQL or dashboard experience is a plus EVEN BETTER… - Experience with outbound communications compliance — TCPA, do-not-call, SMS sender registration, or similar calling/messaging regulations in the US or internationally - Experience at an early-stage startup or scaling product org - Familiarity with OKR frameworks, roadmap tools, or product analytics platforms - Background in product management, engineering, or consulting/strategy with deep operational exposure 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 re