Keynote
Day 2 Keynote
Thursday, Nov 5 | 9:00AM - 10:00AM
Details
See what changes when AI works from a live system of record instead. A missed date surfaces before it becomes a problem. A dependency is flagged before downstream teams are impacted. An entire process runs autonomously, its guardrails built into the sheet itself, not the prompt. Decisions are made with confidence.
This is what AI looks like when it's integrated into your workflows, not a summary export. You'll see it live at this event: how the very sessions you're sitting in were created by humans working together with agents in Smartsheet. Leave with inspiration and momentum leading into the rest of the day’s sessions.
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Location Ballroom 1 - Level 5 |
Speakers
Janelle Milodragovich
VP, AI GTM Strategy
Janelle "Milo" Milodragovich is VP of AI GTM Strategy at Smartsheet, where she leads AI messaging and use case development, external thought leadership, and customer activation programs. Before Smartsheet, she spent two years building Strata, an AI startup delivering research and strategy tools for corporate development teams — experience that shapes her perspective on how enterprises can move from AI experimentation to practical, ROI-driven adoption.
Rajeev Singh
Chief Executive Officer
Rajeev Singh is the Chief Executive Officer and member of the Board of Directors at Smartsheet, an intelligent work management platform trusted by millions of people at companies across the globe, including over 85% of the Fortune 500. He has served as CEO of Smartsheet since October 2025. A proven technology leader and entrepreneur, Singh was the co-founder and President of Concur Technologies, where he helped build the company into the global leader in travel and expense management. In 2014, Concur was acquired by SAP for $8.3 billion—the largest SaaS acquisition at the time—setting a new standard for enterprise cloud valuations. Following his tenure at Concur, Singh served as Chief Executive Officer and Chairman of the Board at Accolade, a pioneer in personalized healthcare navigation. Under his leadership, Accolade expanded its reach to more than 14 million members, transforming how employers deliver healthcare. He led the company to a successful IPO in 2020, and it was acquired by Transcarent in 2025. Singh currently serves on the boards of Basalt Health and Scala.ai, and has previously held board positions with high-growth enterprise technology companies including Amperity, Apptio, and Avalara, where he played a key role in their strategic expansion and public market success. In addition to his corporate work, Singh is deeply committed to community service. He has served on the boards of the Seattle Children’s Hospital Foundation and the University of Washington Foundation, supporting initiatives that drive meaningful impact in healthcare and education.
Rosalie Fenner
Director of Strategic Project Management
Rosalie Fenner is the Director of Strategic Project Management at Advanced Drainage Systems (ADS), an industry leader dedicated to protecting and managing the world's most precious resource, water. With a diverse background spanning product development, product management, marketing, and consulting, Rosalie brings a broad business perspective and a passion for driving strategic initiatives that deliver meaningful results. At ADS, Rosalie leads the Strategic Project Management team, overseeing complex, cross-functional initiatives that support the company's growth and innovation objectives. Under her leadership, the team developed and implemented a stage-gate process for new product development, which has since evolved into a mature framework supporting initiatives across the broader organization. Rosalie and her team also championed the implementation of Smartsheet four years ago and continue to lead adoption efforts, helping teams improve collaboration, visibility, and project execution throughout the company. Known for her ability to align strategy with execution, Rosalie is committed to building scalable processes, fostering cross-functional collaboration, and enabling teams to successfully deliver transformational projects. Outside of work, Rosalie enjoys international travel with her husband Matt, cheering on her niece at dance competitions and her nephew on the baseball field, and passionately supporting The Ohio State Buckeyes.