Rajeev Singh: AI Agents Are the New Users

About this episode

Smartsheet CEO Rajeev Singh on which software survives AI — and why agents, not humans, are the new users.

Rajeev Singh co-founded Concur and sold it to SAP for $8.3 billion, took Accolade public, and nine months ago became CEO of Smartsheet — shortly after Blackstone and Vista took the company private. He tells Sascha Roehrer why Smartsheet went all in on the Model Context Protocol and now builds software for AI agents, not just people. He lays out the three tests that decide which enterprise software vendors stay relevant, and why handing employees an LLM login is not an AI strategy. Also covered: model costs at enterprise scale, regulation in the EU and the US, his advice for founders, and his predictions on the economy and lifespan.

Chapters

• 00:00:00 Why Rajeev Singh came back for one more run
• 00:02:25 The engineer in the CEO
• 00:05:35 What Smartsheet does — and the MCP bet
• 00:07:40 Agents as project managers
• 00:10:13 Model strategy: open source, cost, stability
• 00:12:35 Markets and industries, growth in Germany
• 00:14:48 Blackstone, Vista and the target
• 00:16:21 Which software survives the AI wave
• 00:20:24 Regulation: EU AI Act vs. the US
• 00:22:59 From Concur to Accolade: the founder years
• 00:25:08 Starting a company now — but how?
• 00:28:00 One-person companies and the future of work
• 00:31:13 Why switching on an LLM is not a strategy
• 00:34:19 Boards, healthcare AI and longevity
• 00:38:22 Speed vs. data: 180M automations
• 00:40:02 Hiring for curiosity and grit
• 00:44:22 Smartsheet one year from now
• 00:46:18 Bubble or not? The economic outlook
• 00:51:00 The application layer and data moats
• 00:53:19 The wildest 20-year prediction

Guest:
Rajeev Singh is CEO of Smartsheet, a work management platform with over 100,000 customers, including more than 85% of the Fortune 500. He co-founded Concur (sold to SAP for $8.3 billion in 2014) and served as CEO and Chairman of Accolade (IPO 2020, acquired by Transcarent in 2025). He serves on the boards of Basalt Health and Scala.ai.

Linkedin: https://www.linkedin.com/in/rajeevsinghseattle/
Website: https://www.smartsheet.com/

deeptech Insights:
deeptech INSIGHTS is a long-form interview series for people who think about frontier technology and the future for a living. Host Sascha Roehrer sits down with executives, investors, researchers, and the people shaping what comes next. Produced by Börsenmedien AG, Germany's leading financial media house (DER AKTIONÄR, BÖRSE ONLINE, €uro, €uro am Sonntag).

Youtube English: https://www.youtube.com/playlist?list=PLGwe6Ab4ZdSc
Youtube German: https://www.youtube.com/playlist?list=PLYvuwOqohiSw
Spotify English: https://open.spotify.com/show/033ONjPa8CuRZwJ0wZyWPz?si=c6fe9d33623e4418
Spotify German: https://open.spotify.com/show/033ONlTEHwbLHanLrQ6SeC?si=738da62560ed4cd7
Guest suggestions & feedback: [email protected]

This episode is for informational purposes only and does not constitute investment advice or a recommendation to buy or sell any security.