Today we’d like to introduce you to Cathy Vasilev.
Hi Cathy, thanks for joining us today. We’d love for you to start by introducing yourself.
My journey into financial services started like a lot of people’s — I thought I wanted to be a stockbroker. It didn’t take long to realize that selling mutual funds wasn’t my thing. What actually pulled me in was the rules — the regulations, and the why and how behind them.
I got my start as a Registered Sales Assistant at Smith Barney, supporting a First VP of Investments with new accounts, retirement planning, and client escalations. I loved working with clients, and I was fascinated by understanding why my boss recommended the investments he did.
When I moved to Prudential Financial, I crossed over into the full realm of compliance. I ran compliance oversight for a 60-agent agency across three offices — audits, suitability reviews, marketing approval, licensing, even some HR. It was a huge amount of operational range for one role, and it’s really where I built my “I can run everything” instinct.
At NFP Securities, I led multiple compliance teams and had the privilege of helping build software to ease the compliance burden — both for reps and for the compliance team itself. We were building supervisory systems and review workflows to scale oversight across a large, distributed advisor base, and I kept running into the limits of the tools and the time we had. That’s where the dream of Red Oak began.
In March 2010, I co-founded Red Oak Compliance Solutions in Austin with Stephen Pope and Rick Grashel. The premise was simple, if not easy: the advertising-review tools out there weren’t good enough, and between my compliance background and my partners’ software expertise, we knew we could build something better. We built the operating spine of the company ourselves — hiring, org structure, vendor management, internal controls, and a compliance methodology designed to mirror how regulators actually evaluate firms.
Red Oak grew from a startup into an industry-recognized platform, expanding from advertising review into Disclosure Management, Registration Management, and Complaint Management. Along the way we picked up multiple Inc. 5000 listings, a spot on the Financial Times’ Fastest Growing Private Firms list, and repeated years on the RegTech100 — external validation of the foundation we’d built.
We built out onboarding, implementation, support, and client success into a real organization, for a client base that’s grown to 2,000+ firms globally, including more than half of the top 20 global asset managers. I also became the external compliance voice of the company — advising CCOs, speaking and publishing across the industry, and feeding regulatory change and client feedback straight back into our product direction.
In late 2023, I helped guide Red Oak through our growth-equity partnership with Mainsail Partners, followed by the 2024 acquisition of SiteQuest for website monitoring and internet supervision, and the 2025 acquisition of 4U for marketing material distribution.
It’s kind of amazing, looking back, how directly my earlier roles led me here. I’ve spent over sixteen years turning my own lived compliance experience into the product and the customer organization of a company that now serves the exact kind of firms I used to work inside of. Red Oak was never work — it was a dream fulfilled.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It wasn’t a straight line. Looking back over sixteen-plus years, a few struggles stand out.
In the early days, we were doing everything at once, building the product, selling it, and supporting the clients, all with three founders and no dedicated budget for any one of those functions. You wear every hat because there’s no one else to wear it.
Selling into this industry is its own challenge. Compliance teams are trained to be skeptical, that’s their job, so convincing CCOs and compliance officers to trust a startup with their compliance took real time and real trust-building. There’s no shortcutting that sales cycle.
The regulatory ground never stops moving. SEC and FINRA requirements around marketing and social media keeps shifting, so the platform could never just ship and coast, it had to keep evolving right alongside the rules, indefinitely.
Scaling support and implementation was its own struggle. Going from a handful of early clients to more than 2,000 firms — including over half of the top 20 global asset managers — meant rebuilding our onboarding and support model more than once, all while making sure existing clients never felt the growing pains.
We were also competing against more than just other vendors. A lot of firms had homegrown or entrenched compliance systems already in place, and displacing something that’s “good enough” is a harder sell than displacing a competitor.
And more recently, growth brought a different kind of challenge. Bringing on Mainsail Partners as a growth-equity partner in 2023, and then integrating SiteQuest and 4U through acquisition, meant merging teams, products, and cultures — carefully, so we didn’t lose what made Red Oak work in the first place.
None of it was easy. But every one of those struggles is part of why what we built actually holds up.
Do you have recommendations for books, apps, blogs, etc?
Calm, Burnout: The Secret to Unlocking the Stress Cycle, Multipliers
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