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

Current US Perks & Benefits:

Employer subsidized medical/vision and dental coverage for full-time employees

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 Sick Time Off

US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans

US employees receive 12 paid holidays per year

Up to 24 weeks of Parental Leave

Personal paid Volunteer Day to support our community

Opportunities for professional growth and development including access to Udemy online courses

Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account

Teleworking options from any registered location in the U.S. (role specific)

Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity.

US Base Salary Pay Range

$171,250—$203,750 USD