Company: EngageSmart, Boston, MA
Company Description: EngageSmart is a leading provider of vertically tailored customer engagement software and integrated payments solutions, simplifying customer and client engagement for over 100,000 customers across the country. EngageSmart offers single instance, multi-tenant, true SaaS vertical solutions, including SimplePractice, InvoiceCloud, HealthPay24 and DonorDrive.
Nomination Category: Individual Awards Categories
Nomination Sub Category: Female Executive of the Year – Business Products –11 to 2,500 Employees
 Nomination Title: Cassandra Hudson, CFO
- Outline the nominee's achievements since July 1 2021 that you wish to bring to the judges' attention (up to 250 words):
Total 3 words used.
Not long after joining the EngageSmart team in 2020, Cassandra Hudson helped take the company towards its IPO in 2021. This would be an achievement for any CFO, but Cassandra had an incredibly accelerated ramp-up with barely enough time to become acquainted with the company before what would be a period of enormous growth.
Under Cassandra’s leadership, both the company’s financial function and the finance team have grown quickly, efficiently, and effectively. In its first full year as a public company, 2022, EngageSmart’s total revenue increased 41% compared to calendar year 2021 and in the second quarter of 2023, Cassandra has seen the company’s total revenue grow by 28% compared to Q2 2023.
During this period, the company was recognized by the Boston Business Journal as one of the fastest-growing companies in Massachusetts. BBJ also ranked EngageSmart as the 22nd largest software developer in Massachusetts, and the 97th largest public company in Massachusetts. The company was listed as one of Deloitte’s Fast 500 in both 2021 and 2022.
- Reference any attachments of supporting materials throughout this nomination and how they provide evidence of the claims you have made in this nomination (up to 250 words):
Total 3 words used.
Cassandra Hudson’s remarkable talent has not gone unnoticed, even beyond the walls of EngageSmart. In 2022, she appeared on the CFO Thought Leadership podcast where she discussed having helped take two tech companies public in barely five years. She also shared with Authority Magazine about the lessons she’s learned as such a young c-suite executive in a traditionally male-dominated field.
- Which will you submit for your nomination in this category, a video of up to five (5) minutes, explaining the achievements since July 1, 2021 of the nominated woman, OR written answers to the questions? (Choose one):
Written answers to the questions
- If you are submitting a video of up to five (5) minutes in length, provide the URL of the video here, OR attach it to your entry via the "Add Attachments, Videos, or Links to This Entry" link above, through which you may also upload a copy of your video. If you are submitting written answers to the questions for this category, provide them in the spaces below:
- Briefly describe the nominated individual: history and past performance (up to 200 words):
Total 3 words used.
Cassandra Hudson’s impressive record is only that much more so when you consider she’s just 41 years old and the mother of two children under 10. Before joining EngageSmart in November 2020, Cassandra was at Carbonite, where she became the Director of Finance in under three years. Cassandra managed FP&A and Investor Relations as her team took Carbonite public in 2011. In 2014, Cassandra became VP of Finance and Chief Accounting Officer. At the time of her departure, she had helped grow Carbonite from a $7 million company to a $500 million-plus company. In 2019, she led the financial team in the sale of Carbonite.
It’s no wonder that when Cassandra joined EngageSmart she instantly became vital to the team. Almost immediately after signing on, Cassandra helped take EngageSmart public as one of three female leaders at the helm. Under Cassandra’s leadership, both the company’s financial function and the finance team have grown quickly, efficiently, and effectively. In its first full year as a public company, 2022, EngageSmart’s total revenue increased 41% compared to calendar year 2021 and in the second quarter of 2023, Cassandra has seen the company’s total revenue grow by 28% compared to Q2 2022.
- Explain why the achievements you have highlighted are unique or significant. If possible compare the achievements to the performance of other players in your industry and/or to the nominee's past performance (up to 250 words):
Total 3 words used.
Being the Chief Financial Officer of a public company is a challenge no matter who it is, and only that much more challenging for a young woman. Cassandra Hudson helped take two different businesses public before turning 40. The first company was Carbonite, which she not only helped take public but oversaw its sale in 2019—at the time of her departure, Cassandra had helped take it from a $7 million company to a $500 million-plus company.
She’s made a similarly impressive impact on EngageSmart, despite having been with the company for under three years. With Cassandra as chief financial officer, EngageSmart not only went public, but its revenue increased 41% in its first full year as a public company (compared to 2021) and 28% in the second quarter of 2023 (compared to the second quarter of 2022). At 41 years old, Cassandra’s momentum at EngageSmart has shown no signs of slowing. (And she’s just as ambitious in her capacity as the mother of two children under ten years old.)
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