Sr. Product Manager II (Remote Eligible)

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.

You Will:

• 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

You Have:

• 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
• Fluency in AI/ML concepts: model evaluation, agent architectures, RAG, prompt engineering, quality measurement, and human-in-the-loop patterns
• A track record of making thoughtful prioritization decisions in high-ambiguity environments — you can say “no” to good ideas and explain why
• Strong first-principles thinking: you ask “why does the user need this?” before “how do we build it?”
• A philosophy about where AI should make decisions vs. where users need deterministic control, and the ability to articulate that tradeoff clearly
• 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
• 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
• Experience building or managing evaluation and quality infrastructure for AI/ML systems is a strong plus
• Technical degree or equivalent experience