![Robert Bennett](data:image/svg+xml,<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" fill="%231b1b1b" class="bi bi-person-fill" viewBox="0 0 16 16"><path d="M3 14s-1 0-1-1 1-4 6-4 6 3 6 4-1 1-1 1zm5-6a3 3 0 1 0 0-6 3 3 0 0 0 0 6"/></svg>)
Robert Bennett
Founder at
ENGAGESMART, INC.
Net worth: 192 500 $ as of 31/05/2026
Profile
Robert P. Bennett founded Invoice Cloud, Inc., EngageSmart LLC and Intirion Corp. Presently, Mr. Bennett is Chief Executive Officer & Director at EngageSmart LLC and Chief Executive Officer of Invoice Cloud, Inc. (a subsidiary of EngageSmart LLC). Mr. Bennett is also on the board of Walpole Co-operative Bank. Mr. Bennett previously held the position of President at Paya, Inc. Mr. Bennett received an undergraduate degree from the University of Maine and a graduate degree from Northeastern University.
Known holdings in public companies
| Company | Date | Number of shares | Valuation | Valuation date |
|---|---|---|---|---|
| 12/05/2026 | 27,305 ( 0.14% ) | 192 500 $ | 31/05/2026 |
Robert Bennett active positions
| Companies | Position | Start |
|---|---|---|
| ENGAGESMART, INC. | Founder | 07/12/2018 |
| FORRESTER RESEARCH, INC. | Director/Board Member | 22/07/2024 |
Invoice Cloud, Inc.
 Invoice Cloud, Inc. Packaged SoftwareTechnology Services Provides digital payment, customer engagement and outbound disbursement SaaS solutions | Founder | 01/01/2009 |
Walpole Co-operative Bank
 Walpole Co-operative Bank Regional BanksFinance Provides banking services | Director/Board Member | 01/01/2011 |
SimplePractice LLC
 SimplePractice LLC Packaged SoftwareTechnology Services Develops practice management software for healthcare professionals | Director/Board Member | - |
Former positions of Robert Bennett
| Companies | Position | End |
|---|---|---|
Paya, Inc.
 Paya, Inc. Miscellaneous Commercial ServicesCommercial Services Provides integrated payment and frictionless commerce solutions | President | 01/01/2008 |
Intirion Corp.
 Intirion Corp. Electronics/AppliancesConsumer Durables Manufactures and distributes residential & commercial refrigerators & related appliances | Founder | - |
Training of Robert Bennett
Experiences
Positions held
Active
Inactive
Listed companies
Private companies
Connections
15
1st degree connections
9
1st degree companies
Male
Female
Members of the board
Executives
Linked companies
| Private companies | 9 |
|---|---|
Forrester Research, Inc.
 Forrester Research, Inc. Miscellaneous Commercial ServicesCommercial Services Provides analysis and insight into technology areas such as computing and software | Commercial Services |
Intirion Corp.
Intirion Corp. Electronics/AppliancesConsumer Durables Manufactures and distributes residential & commercial refrigerators & related appliances | Consumer Durables |
Northeastern University
 Northeastern University Other Consumer ServicesConsumer Services Functions as a College/University | Consumer Services |
University of Maine
 University of Maine Other Consumer ServicesConsumer Services Functions as a College/University | Consumer Services |
Walpole Co-operative Bank
Walpole Co-operative Bank Regional BanksFinance Provides banking services | Finance |
Paya, Inc.
Paya, Inc. Miscellaneous Commercial ServicesCommercial Services Provides integrated payment and frictionless commerce solutions | Commercial Services |
Invoice Cloud, Inc.
Invoice Cloud, Inc. Packaged SoftwareTechnology Services Provides digital payment, customer engagement and outbound disbursement SaaS solutions | Technology Services |
SimplePractice LLC
SimplePractice LLC Packaged SoftwareTechnology Services Develops practice management software for healthcare professionals | Technology Services |
EngageSmart, Inc.
 EngageSmart, Inc. Packaged SoftwareTechnology Services Develops digital billing and payment platform for customer satisfaction | Technology Services |
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