# Bob Bennett

> Bob Bennett is the co-founder and founding CEO of InvoiceCloud, the payments business that became part of EngageSmart. Previously the founder of MicroFridge and president of Sage Payment Solutions, he led EngageSmart through its 2021 IPO and retired as CEO in April 2024. He serves on the boards of Forrester, InvoiceCloud, and SimplePractice and supports entrepreneurship programs in the Boston area.

- **Role:** Board member at Forrester; independent board member at InvoiceCloud and SimplePractice
- **Organizations:** InvoiceCloud, EngageSmart, MicroFridge, Sage Payment Solutions, Forrester, SimplePractice, EforAll, The Boston Foundation, Northeastern University
- **Education:** BA in Applied Math and Computer Science, University of Maine, MS in Engineering Management, Northeastern University
- **Known for:** Invented MicroFridge, combining a refrigerator, freezer, and microwave., Co-founded InvoiceCloud in January 2009., Led EngageSmart through its 2021 IPO.

## Career timeline

- **1988** — Founded MicroFridge, Inc.
- **2001-2008** — President of Sage Payment Solutions, beginning in December 2001.
- **2009** — Co-founded InvoiceCloud and became its CEO.
- **2015** — Summit Partners invested in InvoiceCloud.
- **2020** — EngageSmart became the umbrella brand for the growing group.
- **2021** — Led EngageSmart through its September 23 IPO on the NYSE.
- **2024-01** — Vista Equity Partners completed its acquisition of EngageSmart.
- **2024-04** — Retired as EngageSmart CEO.
- **2024-07** — Joined the Forrester board on July 22.

## Achievements

- Invented MicroFridge, combining a refrigerator, freezer, and microwave.
- Co-founded InvoiceCloud in January 2009.
- Led EngageSmart through its 2021 IPO.
- EngageSmart was acquired in January 2024 in a transaction valuing the company at approximately $4 billion.

## Latest updates

- **2026-02** — Former InvoiceCloud executive Matt Braley described Bennett’s mentorship in a Topline interview published February 3.
- **2024-07** — Appointed to Forrester’s board on July 22.
- **2024-04** — Retired as EngageSmart CEO, subsequently serving as an independent director at InvoiceCloud and SimplePractice.

## Links

- LinkedIn: https://www.linkedin.com/in/bob-bennett-488b888/

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Profile page: https://yespress.io/bob-bennett
Published by YesPress — https://yespress.io
Last updated: 2026-10-23