Thinking about selling your software business can be an emotional and confusing time. It’s a decision that can shape both your future success as a founder and affect the legacy of your business. Is it the right time? How can you be sure you’ve found the best new home for your business? What will life be like for you afterwards?
At ClearCourse, we’ve heard these questions many times. That’s why we’ve launched our Founder Insights series, speaking to people who have sold their business to ClearCourse and how they found the acquisition process.
This month we spoke to George Bentley, founder of ThinkSmart Software.
The decision-making process
Q1. What did the business you founded do?
ThinkSmart is a cloud-based software tool for children’s activities providers, enabling them to manage all their administration – from registers and staff or customer management, through to invoicing and payments – all in one central location.
Q2. What problem were you trying to solve?
We wanted to give providers their time back, and stop them having to use multiple manual systems to manage their business. We recognised how time-poor a lot of these people were, and in a business where the focus is teaching children, we wanted to make the day-to-day as easy as possible for them.
Q3. Why were you looking for a new home for your business?
We needed to grow the team and find more expertise. Technology was moving quickly and by joining another larger company, we felt we could reach our goals faster than if we continued trying to work it all out on our own. We were just a small team and so the resource and knowledge the right acquirer could offer we knew would be invaluable.
Q4. Why did you choose to join ClearCourse?
Straightaway it was clear that ClearCourse was the only company that could provide a win-win for both us and our clients. They had the team of experts and technical experience we were searching for, and the access to an embedded payments solution we knew would provide huge benefits to our customers and save them money.
The integration experience
Q5. How would you describe the acquisition process in one sentence?
A rollercoaster of emotions, but ultimately the right choice for our business, our staff and our customers.
Q6. What opportunities has this unlocked that wouldn’t have previously been available?
Loads. We now have access to a much larger team that are full of expertise, resources and support. We have been able to embed payments directly into our software to make the payment process easier for our customers. And the business as a whole has grown both in terms of clients, and with regards to its software capabilities.
Q7. How has been acquired by ClearCourse had a positive impact on your business?
I would say it’s really set us apart from the competition, particularly with regards to payments. We now have the sectors first ever embedded payment solution which has proved to be a real differentiator for our product.
Q8. How are you maintaining your unique company culture and identity while integrated into the ClearCourse community?
Our division listens to us; they ask for our opinions and appreciate the culture we have built. They understand what makes us who we are and allow us to continue operating in the same way with the same values, while supporting us with new growth opportunities at the same time. There’s a really close-knit, friendly culture throughout the wider business and that almost makes it easier for us to continue with our own ThinkSmart quirks and traditions too, because everyone is genuinely interested in what we’re doing and wants to learn from one another. Honestly, it’s better than I could have anticipated.
Looking ahead
Q9. What’s next for your business?
What isn’t? 2026 is going to be a fantastic year of growth for ThinkSmart. We plan to roll out a lot of new features and bring some great new talent into the team, and I’m really excited to see the results both within ThinkSmart, and across the whole Sports & Leisure vertical.
Q10. Thank you, George. Anything else you want to add?
Just that even if you’re in the really early stages of thinking about selling, reach out and get more information. I was pretty blind at the start of the process, but the team guided me through every step of the way, and I haven’t looked back since.
