# Smartsheet — VP, Product Management

- Generated: 2026-08-20 02:56:51 PM EDT
- Original/canonical posting: https://jobright.ai/jobs/info/6a873476d34f700f87fc4240
- Jobright source: https://jobright.ai/jobs/info/6a873476d34f700f87fc4240
- Posted: 2026-08-20 01:08:06 PM EDT
- Valid through: 2026-09-20 01:08:06 PM EDT
- Applicants: Not disclosed
- Work model/location: Remote within the United States
- Employment type: FULL_TIME
- Compensation: $291,000–$339,000
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 59%

## Direct-match strengths

AI products, agentic systems, MCP, automation, responsible AI, analytics, and engineering leadership

## Hard or material gaps

Hard experience gap: the role requires 15+ years as a software product manager and 15+ years as a people manager. Keith's source record supports about four years of formal product management, not 15. GTM ownership is also central.

## Evidence map

1. Applied AI product strategy — direct recent evidence.
2. Agentic systems and MCP — direct.
3. AI evaluation and automation — direct/adjacent.
4. Cloud software — direct.
5. People leadership — long direct history.
6. Fifteen years as a software product manager — unsupported mandatory requirement.

## Full normalized job description

Note: The job is a remote job and is open to candidates in USA. Smartsheet is a work management software company uniting human teams with AI agents to automate tasks and uncover insights. The VP of Product Management will lead the Applied AI product strategy, roadmap, portfolio outcomes, and product management team while coordinating AI initiatives across customer-facing products, platform infrastructure, and specialized agents.
Responsibilities
Lead a high-performing product team focused on defining and executing Smartsheet's comprehensive Applied AI product strategy
Define the strategic roadmap for AI product initiatives — from conversational experiences, MCP, automations, specialized agents, and evaluation infrastructure through to AI-powered features in customer-facing products — ensuring a cohesive, coordinated vision
Own the business outcomes of the AI portfolio — define the success metrics (adoption, retention, expansion, and revenue impact), set the targets, and hold the team accountable to them
Instrument, measure, and iterate: build the data and evaluation foundation that tells us whether AI features are actually working, and use it to make hard prioritization calls — including what to sunset
Move fast in a fast-moving space — ship, learn, and adjust in short cycles rather than waiting for perfect information
Lead cross-functional alignment with Product Marketing, Pricing and Packaging, and Sales to shape the Go To Market strategy that positions Smartsheet's AI advantages and educates the market
Partner with Customer Excellence and Sales leadership to ensure your AI product strategy addresses customer needs around AI implementation, responsible AI governance, and AI-powered automation
Work with design leadership to establish a vision for compelling, intuitive AI experiences that are accessible and trustworthy across all customer segments
Stay informed of AI market trends, competitive innovations, and emerging use cases to inform your strategic recommendations and keep Smartsheet at the forefront of AI-driven work management
Build and develop a world-class product management team, establishing clear goals around AI strategy execution and product impact
Skills
15+ years experience as a product manager for a software product
15+ years experience as a people manager
Experience developing and shipping AI features or AI-powered products, with deep familiarity with generative AI, agentic systems, and responsible AI practices
Experience working with UX and engineering teams; deep commitment to customers and team collaboration
Passionate drive and extraordinary ability to communicate with customers, colleagues, and executives
Passion for web-based business software
Ability to evaluate and discuss technical concepts
Experience working with data analytics and visualization
B2B or B2C cloud experience preferred
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)
This role will be eligible for a market competitive incentive opportunity.
Company Overview
Smartsheet is a cloud-based work management platform that empowers collaboration, drives better decision-making, and accelerates innovation. It was founded in 2005, and is headquartered in Bellevue, Washington, USA, with a workforce of 1001-5000 employees. Its website is https://www.smartsheet.com.
Company H1B Sponsorship
Smartsheet has a track record of offering H1B sponsorships, with 17 in 2026, 53 in 2025, 58 in 2024, 46 in 2023, 57 in 2022, 32 in 2021, 41 in 2020. Please note that this does not guarantee sponsorship for this specific role.

## Artifact metadata

- Resume and cover letter: Not generated under the fit gate.
- Google Drive used: No