Like many great entrepreneurial journeys, the EngageSmart story was born from a simple premise – that paying a bill online “shouldn’t be that hard”. From this foundation, EngageSmart worked to set a new standard for dependable, frictionless interactions between companies and their customers, offering vertically tailored customer engagement software and integrated payments capabilities that seek to simplify digital adoption and self-service. We are proud to share the company’s story, from its founding in 2009 to its 2021 IPO, and — in the words of Founder and CEO Bob Bennett — “the three keys” to the company’s success.

”It Shouldn’t Be That Hard”

The EngageSmart story begins in 2009 when CEO and Co-Founder Bob Bennett’s frustration while paying a utility bill sparked this entrepreneurial journey. The simple premise that going paperless and paying a bill online “shouldn’t be that hard” led Bob and his co-founders – all industry veterans in electronic payments – to launch InvoiceCloud, the predecessor company to EngageSmart, in 2009.

We met Bob a few years later, and by that time InvoiceCloud was making bill presentation and payment easier for hundreds of clients across local government and public and private utilities, driving significant increases in self-service and saving time for clients and their customers alike. Our relationship with Bob was initially grounded in a shared understanding that consumer preferences and expectations for digital experiences were outpacing the capabilities for many organizations. We recognized that the innovation, elegance and ease-of-use we saw and experienced within industries like search, shopping, travel and entertainment simply wasn’t found in the billing and payments space. Together with the InvoiceCloud team, we saw an opportunity to bring the company’s client engagement solutions to other verticals where digital adoption lagged. Over the next few years, we worked alongside Bob and the team to help the company execute an organic and acquisition-driven growth strategy that expanded the company’s reach to new markets, including healthcare & wellness, financial services and charitable giving.

“Building a Culture of Excellence to Fuel our Continued Growth”

Since Summit’s founding, we’ve partnered with hundreds of founder-led companies, including more than 70 the last five years alone. This experience has fostered a deep appreciation and understanding for the tenacity and focus required to scale a business and a culture. Over the course of our partnership with EngageSmart, we’ve been continually inspired by the team – and in particular by Bob’s leadership, vision and commitment to his people and customers. As EngageSmart completes its IPO (NYSE: ESMT), we are delighted to share, in Bob’s words, the three foundational principles at the heart of the company’s success to date.


“We are a people-first organization, and this extends beyond employees to include our customers, their clients, our partners, and our investors. Their opinions, needs, and aspirations drive us, and we strive to respond with transparency and a sense of urgency. We promote a customer-first organizational model that places customers at the top of our organizational chart.”


“We believe that the best product wins, and we are motivated by the ongoing pursuit of innovation and market leadership. Our software is mission-critical for our customers and therefore difficult to replace, resulting in very high customer retention. While some software offerings grow complacent in this position, our collective competitive spirit drives us to constantly invest in our solutions and deepen the value they deliver. The journey never ends.”


“We recognize that our solutions operate within an ecosystem, and we view all participants in this ecosystem as our partners. This includes our customers, the adjacent software and service providers they may use, and their clients. By viewing these constituents as partners and treating them as such, we accrue the benefit of focused product feedback and enhanced distribution, which have helped drive our organic growth.

“Our view of partnership also extends to our customers’ communities, where we hope to make an impact through engagement. Our customers play an incredibly important role in their communities by serving a wide variety of wellness seekers (mental and physical health), non-profits, taxpayers, utility customers, financial service consumers, and medical patients. We are proud of the small part we play in these communities by providing solutions that are easy to deploy and use, that address their unique functional requirements, and that turn complex processes like payments and self-service into engaging digital experiences.”

EngageSmart: Growth Timeline


Launched charity streaming – live streaming fundraising

General Atlantic invests alongside Summit and management team


Completes IPO on September 23 (NYSE: ESMT)

EngageSmart 2021:
By the Numbers

Over the course of a decade, EngageSmart translated founder vision into customer reality. We’re proud to celebrate the company’s achievements and evolution.


transactions processed




dollar-based net retention rate


total addressable market

Dollar-based net retention rate shown for the year ended December 31, 2020. All other figures shown as of last twelve months ended June 30, 2021

Stories from the Climb

At Summit, it’s the stories that inspire us – the problems being solved and the different paths each team takes to grow a business. Stories from the Climb is a series dedicated to celebrating and sharing the challenges of building a growth company. For more Stories from the Climb and other Summit perspectives, please visit our Growth Company Resource Center.