ComplySci’s Kadomatsu on Balancing Dealmaking With Leadership

Amy Kadomatsu of ComplySci Shares How to Execute Acquisitions While Leading a Firm as CEO

Janeesa Hollingshead, Senior Editor, Wealth Solutions Report

While dealmaking from the point of view of a banker or private equity professional can be intense and time-consuming, making deals while simultaneously heading a company as CEO reaches another level. 

With the heavy responsibilities that rest on a CEO’s shoulders, it takes highly developed leadership skills to also lead a firm through a string of acquisitions and integrations. 

A great leader isn’t set to lead, she’s set to make a difference.

WSR Pathfinder Awards – Top Women Dealmakers in Wealth Management honoree Amy Kadomatsu does just that. 

As CEO of regulatory technology and compliance solutions provider ComplySci, Kadomatsu has led the firm through three acquisitions expanding the company from 84 employees in March 2021 to over 300 today: RIA in a Box, illumis, and National Regulatory Services.

We caught up with Kadomatsu to learn how a person balances the duties of CEO and leading acquisitions, as well as M&A strategies and what inspired her to enter fintech. 

WSR: How did you decide to get involved in technology and in fintech? Was there a pivotal moment or series of events that led you in that direction?

Kadomatsu: My first business school internship was with SoftBank Technology Ventures, one of the earliest investors in some of the biggest names in e-commerce and internet-enabled businesses. The work supported by their investments enabled the digital revolution that provides the infrastructure we use across every industry today.  

Amy Kadomatsu, CEO, ComplySci

Around this time, I met David Eisner, who now sits on my board of directors. David was a force in the development of the fintech sector and he helped me marry my interest in technology and experience in financial services within this emerging space. 

The end of business school provides the perfect opportunity to pivot. With my experience within the investment banking world, recent exposure to the emerging fintech space and academic training, I was able to step back and understand what I really wanted to do was sit on the other side of the table – and run companies. Specifically, fintech firms.

Take a step back, assess, then take 2 steps forward.

WSR: You are in a space where you’re both a dealmaker for your company and managing the company itself. How do you strike that balance?

Kadomatsu: I believe the best way to build a business is through a deep understanding of the customer journey. Working with the product development team, following market trends and shifts in demand leads to a better-informed leadership of a company. But I’ve always had a foot in two worlds because I very much love the deal process. 

To straddle this line, leaders need to understand how to balance working on the company vs. working in the company. Our incredible executive team and leaders throughout the organization have the operational expertise and strategic mindset that allows me to focus on the company while they take care of tactical execution. 

While there will always be something that can pull me back into the day-to-day operations, I’m able to step away from these details and focus on the bigger picture for longer periods because of our team.

WSR: What strategy or criteria do you employ when you look for a potential M&A transaction? Can you tell us about your future plans?

Kadomatsu: Our top priority and guiding principle for product development, growth and user experience is to be every chief compliance officer’s first call for help. This north star provides the context for our M&A activity. 

While of course a deal must make financial sense for us to pursue, if the organizations and cultures don’t seem to align with the goal of supporting financial services CCOs, we likely will not move forward. 

It doesn’t matter if you walk or run. What matters is you’re advancing.

We’ve been very lucky to experience significant M&A-based and organic growth over the last year and will continue to explore strategically aligned, smaller and transformative acquisitions. Our investors truly believe in our approach and have encouraged us to think expansively about these kinds of plans. 

Our highly collaboratively process with our investors has positioned us to be a force in the continued consolidation we see across the industry, and we expect to remain active moving forward.

Janeesa Hollingshead, Senior Editor at Wealth Solutions Report, can be reached at

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