Press release

EngageSmart Expands Leadership Bench with New Hires

Sponsored by Businesswire

EngageSmart, the leading provider of vertical-specific SaaS solutions that simplify consumer engagement and ecommerce, has been steadily adding high-caliber talent from the region’s fastest-growing technology companies over the last year. New hires across the organization are all proven leaders in rapid-growth technology companies.

Executive hires in the last six months include:

  • Chief Marketing Officer Alison Durant, formerly of LogMeIn and Oracle
  • Chief Financial Officer Cassandra Hudson, formerly of Carbonite, Inc.
  • General Counsel Charles Kallenbach, formerly of Phreesia, Inc. and Heartland Payments

These new executive employees join an already robust leadership team that includes:

  • CEO and founder Bob Bennett, who has a long track record building high-growth companies and successful teams
  • President of Enterprise Solutions Tom Griffin, formerly of Demandware and Salesforce
  • Chief People Officer Kristen Kenny, formerly of CarGurus, HubSpot, and Endeca
  • Chief Technology Officer Frank Laura, formerly of Quicken Loans and Progressive Learning
  • Chief Strategy Officer Jonathan Seltzer, formerly of CLEAResult
  • President of SMB Solutions Howard Spector, also co-founder of SimplePractice
  • Chief of Staff Barry Anderson, formerly of Harris Computer

Open headcount across the organization reflects exponential growth across all EngageSmart’s solutions including Invoice Cloud, SimplePractice, HealthPay24, DonorDrive, and IVR Technology Group.

“With outsized growth comes enormous opportunity to expand on our mission, advance our technology, and foster an amazing culture,” says EngageSmart CEO Bob Bennett. “We are thrilled to have a leadership team in place with the experience, drive, and people-first approach to continue building on our success.”

About EngageSmart:

EngageSmart serves vertical industries with true SaaS Solutions that simplify client and customer engagement through software and ecommerce. EngageSmart’s solutions use cloud-based technology to simplify everyday, essential tasks and services that are the building blocks for great customer relationships. Founded as Invoice Cloud in the electronic payments space in 2009, EngageSmart’s solutions include Invoice Cloud, SimplePractice, HealthPay24, DonorDrive, and IVR Technology Group. Every EngageSmart solution supports essential tasks and services in verticals historically challenged by digital transformation, including tax, utilities, insurance, healthcare, fundraising, and more. EngageSmart is creating the standard for dependable, frictionless interactions between companies and their customers. To learn more, visit