EngageSmart began with a founder who was annoyed by paying a utility bill. Bob Bennett thought it "shouldn't be that hard," and the phrase became his company's creed. He launched InvoiceCloud to let towns, utilities, and insurers take payments online. EngageSmart later added SimplePractice, software that therapists and other clinicians used to book, bill, and see clients. When it went public in September 2021, telehealth had made SimplePractice a pandemic necessity.

From MicroFridge to InvoiceCloud

Bennett's first company, MicroFridge, made small fridge and microwave units. He later ran Sage Payment Solutions. In 2009 he became chief executive of InvoiceCloud, which he started with co-founders. In 2018 and 2019, the growth investor General Atlantic built EngageSmart around InvoiceCloud and SimplePractice. The bet was that small, overlooked industries were still paying on paper. Each product earned subscription fees and a share of payments.

Two Years on the NYSE

EngageSmart priced its offering at $26 a share on September 22, 2021, and listed on the New York Stock Exchange as ESMT. General Atlantic kept control after the deal. SimplePractice also ran Monarch, a marketplace that connected clinicians with people seeking therapy. In 2023 Vista Equity Partners agreed to take it private, and EngageSmart left the NYSE in January 2024. It now operates as a private company.

Cover: Reading a Letter, Furuyama Moroshige. Art Institute of Chicago, public domain. Chosen for reading a letter (the bill that shouldn't be hard).