Sr. Product Manager II (Remote Eligible)

Smartsheet is a company that empowers teams to manage work seamlessly and scale solutions smarter. They are looking for a Senior Product Manager to own the roadmap for their AI-native products serving enterprise customers, focusing on user research and prioritization to ship complex capabilities. The role involves mentoring other PMs, establishing metrics, and collaborating with cross-functional teams to ensure successful product delivery.

Responsibilities:

• 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

Requirements:

• 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
• Technical degree or equivalent experience
• Experience building or managing evaluation and quality infrastructure for AI/ML systems is a strong plus