Our next chapter has begun.

When we started Checkmate about 5 years ago, we had no more than some computers, a whiteboard, and a small office at 1253 Whitney Ave overlooking a graveyard.  There was no portfolio of work, no reputation or demonstration of digital skills; we survived because of odd jobs on Upwork and making phone calls to every contact we had, looking for a chance....

It’s a common origin story - one that many entrepreneurs and startups share. But the journey we took and people we’ve met since opening our doors have been anything but ordinary.

One thing led to another, we found incredible local talent and started taking on bigger projects. As years passed, we found ourselves on the train to NYC more often every month. We watched as the Connecticut ecosystem continued to grow and started working with amazing local companies like Green Check Verified and Odin Answers. We continue to see New Haven blossom with District, Collab, Health Haven Hub, and IMPACT moving to town, while the Hartford community poured their hard work into spaces like Upward Hartford, and programs like Startup Bootcamp and Techstars lay roots into the city. We continue to see the Stamford entrepreneurship community grow as well, with programs like Stamford Innovation week. We’ve been delighted to actively participate in these programs, events, and communities over the years, giving us a front row seat to watching our state evolve and embrace the ‘startup world’. We’d like to give a state-wide thank you to CT Innovations and CT Next too. On a fundamental level, these organizations brought people together, an essential ingredient for the ecosystem that helped us to grow and flourish.

In 2019 we started the year focusing on making our process repeatable, impactful, and digestible for large enterprises and young startups. The Design Sprint process grew into our flagship service offering, helping companies save months of time and effort.  As our services matured, so did the operations of our business.

That’s where one of our partners, MindTrust, came into the picture. MindTrust is a global innovation company with roots in software development and digital marketing. MindTrust invents products, platforms, and next generation technologies for clients spanning Fortune 10 companies, top tech startups, governments, universities, and just about everybody in between. Over the years, we’ve worked closely together on a number of exciting projects and joining forces was a natural progression. Chris and his team have been working to solve the issues inherent to scaling and accelerating innovation. With Checkmate’s design process achieving better results faster, and MindTrust’s development of the first Team as a Service (TaaS) platform, we knew that this was the right move at the right time.

We have been lucky to say the least. The amount of support over the years from partners, advisors, employees, professors, alumni, friends and family has been humbling and overflows our hearts with gratitude. Thank you for pushing us, believing in us, and sharing your contagious optimism to build something great. We will hold your support with us in all our future endeavors, and especially as we enter this new chapter. Every conversation has mattered more than we can describe.

Lastly, to our new family at MindTrust, thank you for the opportunity. Let's crush it.

🤜❤️🤛
With gratitude and appreciation,
Tom & The Checkmate Digital Team


February 1, 2015

Open for Business!

On February 1, 2015, we landed our first (and last) website for $500.
(Thanks for believing in us Bobby! Keep crushing it at
Lilo Social)

2016 - 2018

"The Techies in the Basement"

Now with the whole basement to ourselves, we had the space to add staff.
Then we landed our first $100k+ deal, and started to celebrate holidays as a big family.

2018 - Present

New Haven for the Win!

Downtown was the spot! Bootstrapped, we grew to 18 people.
We won some awards, and started internal projects that would shape our future.

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