# Arlo Gilbert

> Arlo Gilbert is the co-founder and founding CEO of Osano, where he became chief innovation officer in July 2025. A software entrepreneur and investor based in Minneapolis, he previously co-founded iCall and Meta SaaS, which Flexera acquired in 2018. He wrote The Privacy Insider, hosts its companion podcast, and now works on generative AI systems and privacy technology.

- **Role:** Co-founder and Chief Innovation Officer at Osano
- **Organizations:** Osano, Meta SaaS, Flexera, iCall
- **Education:** The University of Texas at Austin
- **Known for:** Co-founded Meta SaaS and led it through its acquisition by Flexera in 2018., Co-founded Osano and led it as founding CEO through its 2023 Series B., Author of The Privacy Insider: How to Embrace Data Privacy and Join the Next Wave of Trusted Brands.

## Career timeline

- **2010** — As iCall CEO and co-founder, participated in the rollout of internet calling over cellular 3G on iPhone; a later provider announcement reported more than five million iCall downloads.
- **2016** — Co-founded Meta SaaS with Scott Hertel; published an essay criticizing the impending shutdown of the Revolv smart-home service.
- **2018-05** — Flexera acquired Meta SaaS and renamed the product Flexera SaaS Manager.
- **2018-10** — Co-founded Osano with Scott Hertel and served as founding CEO.
- **2019-10** — Presented Osano at TechCrunch Disrupt San Francisco with Scott Hertel.
- **2023-08** — Osano announced a $25 million Series B led by Baird Capital during his tenure as CEO.
- **2024-04** — Published The Privacy Insider and launched its companion podcast.
- **2025-07** — Announced Bobby Jaffari as successor CEO and became Osano’s first chief innovation officer.
- **2026** — Published writing about AI-assisted development and Osano’s privacy-trained AI assistant.

## Achievements

- Co-founded Meta SaaS and led it through its acquisition by Flexera in 2018.
- Co-founded Osano and led it as founding CEO through its 2023 Series B.
- Author of The Privacy Insider: How to Embrace Data Privacy and Join the Next Wave of Trusted Brands.
- Host of The Privacy Insider Podcast.
- Co-founded iCall, whose network provider reported more than five million downloads in October 2010.

## Latest updates

- **2026-09** — The Osano AI essay index lists a September 28 article by Gilbert about responsibility when AI agents remain within technical boundaries.
- **2026-07** — His July 16 Osano newsletter discussed the company’s privacy-trained AI assistant, legal citations, and escalation to qualified human experts.
- **2026-04** — Published AI Coding Got Boring, reflecting on the changing experience of software development with AI agents.
- **2025-07** — Moved from Osano CEO to its first chief innovation officer; Bobby Jaffari became CEO.

## Links

- Website: https://arlo.is/
- LinkedIn: https://www.linkedin.com/in/arlogilbert/
- Twitter/X: https://x.com/arlogilbert
- GitHub: https://github.com/arlogilbert/

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Profile page: https://yespress.io/arlo-gilbert
Published by YesPress — https://yespress.io
Last updated: 2026-10-21