Servant leadership permeates our organization and underpins our growth mindset. We believe the best leaders empower their teams to excel. Our employees feel supported to respond rapidly, innovate quickly, and build effectively, enabling us to maintain product leadership and help our customers improve their organizations and better serve their communities.
Robert P. Bennett
CHIEF EXECUTIVE OFFICER
Bob is the founder and CEO of EngageSmart, which he launched in 2020. He has over 30 years of experience in technology, working with everything from computer software to payments to appliances. Bob founded his first company, MicroFridge, Inc., in 1988, and went on to other technology leadership positions, including as President of Sage Payments, before founding InvoiceCloud in 2009. Throughout his career, Bob’s focus on technological innovation, honest competition, and servant leadership have remained constant.
Bob loves his family, working, socializing and playing squash. He can be a bit competitive and believes it’s related to growing up in a large New England family, “You have to have lived through long winters with lots of brothers and sisters to truly understand it. Go Sox!”
CHIEF FINANCIAL OFFICER
Cassandra joined EngageSmart in 2020 and serves as the company’s CFO. She most recently served as the Chief Accounting Officer and VP of Finance for Carbonite, Inc. which was sold to OpenText in December 2019, where she had direct responsibility for all aspects of the corporate finance function including FP&A, accounting, revenue operations, internal audit, tax and treasury. She is a results-driven corporate finance executive with deep experience in building, leading and advising companies through rapid growth, capital markets transactions, international expansion and M&A activity. Cassandra lives in Lakeville, MA with her husband and two children and enjoys running in her free time.
PRESIDENT, SMB SOLUTIONS
Jonathan serves as President of EngageSmart SMB solutions, including SimplePractice and its ecosystem of products. Jonathan joined EngageSmart in 2019 as Executive Vice President Business and Corporate Development and managed EngageSmart’s strategic business initiatives, M&A, and integration activities. Prior to joining EngageSmart, Jonathan served as CFO and Head of Corporate Development at CLEAResult Consulting Inc., the largest outsourced implementer of demand response and energy efficiency customer engagement programs to North American electric and gas utilities. Prior to CLEAResult, Jonathan has broad corporate finance experience with KRG Capital Partners, a middle-market private equity firm and investment banking at Wachovia Securities and Piper Jaffray.
CHIEF OF STAFF
Barry serves as EngageSmart’s Chief of Staff. Barry joined the company in 2014 to lead business development for InvoiceCloud. Prior to joining the InvoiceCloud, Barry served as the Director of Initiatives with Harris Computer where he was instrumental in building a network of fully integrated payment processing partnerships serving the government and utility marketplace. He has 30 years of government ERP experience.
Barry’s passions include his faith, family, friends and a regular contentious game of pickup basketball. When most discover that he is a proud Southern Illinois University Saluki, two consistent questions are posed; “you actually graduated” and “what’s a saluki”!
CHIEF MARKETING OFFICER
As CMO of EngageSmart, Alison leads all aspects of marketing. Prior to joining EngageSmart in 2020, Alison spent five years as SVP Marketing at LogMeIn where she played a key role in the company’s rapid growth and expansion to become one of the industry’s leading SaaS organizations. Alison joined LogMeIn from Oracle where she held leadership positions in Oracle’s applications business, following Oracle’s acquisition of Endeca. Alison has a track record for building high-performing Marketing teams with decades of go-to-market experience from small private organizations to the world’s largest technology providers.
Alison splits time between Sunapee, NH and So. Dartmouth, MA with her husband and two teenagers.
Charles joined EngageSmart in 2021 and serves as the company’s General Counsel, with responsibility for legal and regulatory functions. He most recently served as the General Counsel for Phreesia, Inc., a healthcare software-as-a-service company, that had a successful initial public offering in July 2019. Charles has been working in-house for public and private technology companies in the payments, healthcare, and telecommunications sectors, and has experience building legal, risk, ethics and compliance functions. He started practicing as an attorney at Jones Day in Washington, D.C..
Charles lives in Ambler, PA with his wife, and has three children and one dog. He enjoys cycling, hiking, swimming and Philadelphia sports.
CHIEF PEOPLE OFFICER
Kristen has worked within the People Function for the past 20+ years. Prior to EngageSmart, she served as CarGurus VP People & Talent. Kristen previously held senior-level HR leadership roles at HubSpot and Endeca. Through her career, Kristen has focused her efforts on start-up companies to build infrastructure around HR/recruiting operations and business expansion. She holds a Bachelor of Science from Westfield State University.
Kristen has a 2-year-old daughter. She loves the beach, golfing and New England sports (especially the Bruins and Patriots).
CHIEF TECHNOLOGY OFFICER
Frank Laura joined EngageSmart in August of 2019 as the Chief Technology Officer. Frank’s role is well-matched for his experiences at building, leading, and improving high-performing technology teams, processes, and cultures in fast-growth companies. He brings decades of knowledge, skill, and perspective from his leadership roles in public and private companies like Quicken Loans, Progressive Leasing, and Aaron’s.
While technology has been in his blood from childhood, Frank has grown a greater passion for his wife and two sons. He enjoys outdoor leisure activities like mountain biking, cycling, skiing, fishing, boating, and ATV’ing.
FOUNDER & SENIOR ADVISOR
Howard is Co-founder of SimplePractice and serves as a Senior Advisor to EngageSmart. Howard has over 20 years of experience in the information technology industry. He is proud to have earned his MA in Counseling Psychology with an emphasis in Depth Psychology at Pacifica Graduate Institute.
Why Join EngageSmart?
Our mission is to simplify customer and client engagement. This allows our customers to focus their time and energy on initiatives that improve their organizations and better serve their communities.
We are a people-first organization, and this extends beyond our 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 urgency.