A couple of months ago, Georgio Anastasi joined Checkstep as our Chief Operating Officer and Chief Financial Officer. He's spent over 24 years building and scaling SaaS companies across alternative assets, AI, fintech and telecommunications, most recently leading FullCircl through a successful exit at a 7.5x ARR multiple, and helping VC and PE-backed businesses raise capital, tighten operations and prepare for what's next.
He brings a rare breadth of experience to the role - the kind that comes from building financial and operational discipline across very different markets rather than one. We sat down with him to talk about that journey, what he's learned in his first few months and what he's focused on as Checkstep scales.
1. You've spent your career across some very different industries. What draws you to a new sector each time?
Finance travels well. Every industry needs the same fundamentals: cash discipline, forecasting, capital structure. The only variable is the product. What I actually screen for when I move is the company, not the sector: fast-growing, international businesses where the fundamentals matter more than the label on the door.
2. Trust & Safety is new territory for you. What made you want to join Checkstep specifically?
Two things. The first is the mission. Trust & Safety is about our security as humans, and the online safety landscape has never mattered more than it does right now. I wanted to be part of the force driving that forward rather than watching it happen. Checkstep's place in its lifecycle sealed it: a business scaling internationally is exactly the stage where I know I add the most value.
The second is the people. Guillaume Bouchard, our CEO and Founder, sold his previous company, Bloomsbury AI, to Meta, and he's one of the most well-connected and well-regarded people in the T&S space. Through our conversations it became clear I could work with him as a true partner - to him and to the business. Just as important, I met the wider executive team during the interview process: Geoff Johnston (VP Product), Emily Atkinson (Head of Marketing), Vincent Maurin (CTO), Hill Stark (VP Partnerships) and Deniz Atabey Alkan (VP Trust & Safety). Meeting your peers before you join matters more than people realise. We clicked immediately, and it's proven itself since, because we work exceptionally well together. A mission I believe in, a company at the right stage and a leadership team I wanted to build alongside is what made it Checkstep and not somewhere else.
3. You led FullCircl through its $135m sale to nCino and raised $10m in debt financing along the way. What did that experience teach you about building a company that's ready for its next stage?
We raised $10m through a debt refinancing to redeploy capital and expedite growth, which turned out to matter more than I expected. It wasn't money to survive on. We were structuring the balance sheet to make FullCircl an obviously attractive acquisition target, and that work paid off when nCino acquired us.
The lesson: being ready for the next stage isn't something you scramble to build when a buyer shows up. It's a posture you hold continuously: clean financials, a capital structure that gives you optionality rather than boxing you in, and a growth trajectory a buyer can underwrite with confidence. By the time the right conversation happens, the diligence should already be done.
4. As both COO and CFO, how do you think about balancing operational execution with financial discipline?
I don't really treat them as two things to balance. They're the same job viewed from different angles. Financial discipline without operational context is just reporting; operational execution without financial discipline is just activity. My job is to make sure capital only moves toward what's actually driving the business forward, and that means staying close to GTM strategy, team alignment and day-to-day execution to know where that is. Finance isn't a function that sits behind the business anymore. It's the operating system running underneath it.
5. What's surprised you most in your first couple of months at Checkstep?
The calibre of the team. In most companies, people arrive because the role came up and the timing worked. Here, almost everyone chose this space deliberately. They wanted to work on online safety specifically, and it shows in how people operate: more conviction, and genuine debate about getting the mission right rather than simply hitting targets. It's rarer than it sounds, and it changes the texture of the whole company.
The other surprise has been how fast the regulatory landscape is moving. The DSA and frameworks like it aren't theoretical anymore. They're driving real urgency, because large corporations are being fined millions for getting this wrong, and what we've built is the protection they need against that exposure.
6. What are you most focused on over the next six to twelve months?
Growth, and the capital to fund it. We're targeting significant ARR growth from December 2025 to December 2026. On the international side, the US and Asia are the priority: both are markets where regulatory pressure and customer demand are accelerating at the same time. My focus is making sure the capital and the operational structure are both ready to support that pace rather than chase it.
7. Having worked across many different industries, what patterns or lessons do you find yourself bringing with you wherever you go?
The biggest lesson is simple: don't assume. Don't assume the financial picture you inherit is complete until you've rebuilt it from first principles yourself. Don't assume setting up in a new country will work the way it did in the UK, because it never does. Every sector I've moved into has punished an assumption I didn't know I was making, so now I go in expecting to be surprised.
As for patterns, I bring the same things everywhere. High energy. A habit of getting the entire company involved in the numbers rather than keeping finance in a corner. And a determination to put finance on the map as a driver of the business, not a department that reports on it afterwards.
Every industry Georgio has worked in has sharpened the same instincts: how to build financial rigour into a scaling business, how to get a company ready for its next milestone and how to turn operational discipline into commercial results. Those are exactly the muscles Checkstep needs as we grow, and that's what he'll be bringing to the table every day.
Welcome to the team, Georgio.
