Senior Product Manager

• We are looking for a Senior Product Manager to own the roadmap for one of our AI-native products serving enterprise customers
• You’ll ship complex, technically demanding capabilities end-to-end, staying grounded in deep customer research while navigating the genuine ambiguity of what’s possible with AI today
• If you think in first principles, stay grounded in customer research, ship with discipline, and can navigate the messiness of building genuinely AI-native products at enterprise scale — this is your role
• You’ll report to a Director of Product Management located in our Bellevue, WA office, or you may work remotely from anywhere in the US where Smartsheet is a registered employer
• Own the strategy, roadmap, and execution for an AI-native product — defining what gets built, in what order, and why, through user research, first-principles thinking, and ruthless prioritization
• Ship incrementally and deliberately, treating AI capabilities like any other product bet: start small, measure impact, learn, iterate — not waiting for the “perfect” model or feature
• Obsess over user experience and outcomes — the fact that something uses AI doesn’t matter if it doesn’t solve a real problem faster, clearer, or more confidently than the alternative
• Establish clear success metrics and evaluation frameworks that measure what users actually care about — speed, confidence, accuracy, trust, usability — not just model performance in a vacuum
• Define the standards and best practices that help other teams build AI capabilities successfully, not just your own
• Build strong cross-functional partnerships with engineering, design, and data science, where all perspectives shape decisions — not just “can we build this?” but “should we?”
• Work closely with GTM partners to define positioning, messaging, and sales/customer success enablement — you own the narrative around what this product does and doesn’t do
• Operate comfortably in genuine ambiguity and with a high degree of autonomy, and help the people around you do the same
• Mentor and develop other PMs
• Use AI tools extensively in your own work and feed what you learn about limitations, UX, and possibilities back into product decisions

Benefits

• Lucrative Employee Stock Purchase Program (15% discount)
• 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
• Monthly stipend to support your work and productivity
• Flexible Time Away Program, plus Incidental Sick Leave
• Up to 24 weeks of Parental Leave
• Personal paid Volunteer Day to support our community
• Opportunities for professional growth and development including access to LinkedIn Learning online courses
• Company Funded Perks, including a counseling membership, primary care membership, local retail discounts, and your own personal Smartsheet account
• US employees receive 12 paid holidays per year
• US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
• Teleworking options from any registered location (role specific)
• HSA, 100% employer-paid premiums, or Buy-up medical/vision and dental coverage options for full-time employees
• Equity - Restricted Stock Units (RSUs) with all offers
• Monthly contributions toward your pension
• Mployer-paid Private Medical and Dental, additional cost for family members- A track record of making thoughtful prioritization decisions in high-ambiguity environments — you can say “no” to good ideas and explain why
• Hands-on experience using AI tools (Claude, ChatGPT, etc.) as part of your own workflow, and the ability to extrapolate from that to what enterprise users need
• 8-10+ years of product management experience shipping complex, technically demanding products end-to-end, from conception through launch and iteration
• Direct experience working with enterprise customers and scaled organizations — you understand the complexity of managing work at scale and the constraints that come with governance
• Experience building or managing evaluation and quality infrastructure for AI/ML systems is a strong plus
• A philosophy about where AI should make decisions vs. where users need deterministic control, and the ability to articulate that tradeoff clearly
• Technical degree or equivalent experience
• Comfort with both technical depth and creative ambiguity — you can have a detailed architecture conversation and also challenge the underlying assumptions
• Exceptional communication skills and the ability to influence without authority
• Strong first-principles thinking: you ask “why does the user need this?” before “how do we build it?”
• Fluency in AI/ML concepts: model evaluation, agent architectures, RAG, prompt engineering, quality measurement, and human-in-the-loop patterns