The Finality of Infinity and Beyond

June 2018 – Now that the acquisition and transition mission was successfully complete, having guided the IT, Support, and Operation departments to become one Cleo, it was time to start focusing on another growth stage for the company. We dubbed it “Mission: Customer Success”.

Customer satisfaction and loyalty is critical to any business, and Cleo was no exception. The team was also keenly aware that the rapid growth we were experiencing could leave customers feeling like sheer numbers rather than valued users of our software. We needed to grow AND retain our clients.

With that mission in mind, we launched a test program, working with some of our most complex clients, to establish a base line for where we needed to focus our efforts. For six intense months, I led the Customer Success team, traveling to and meeting with these clients, understanding their implementations, how they were utilizing Cleo’s platform, and where they planned to expand Cleo’s use. With the data collected, Cleo had the insights it needed to design and develop a robust customer success department; based not on what we “thought” our customers would like, but on their actual challenges and their input for a better experience.

January 2019 – A new #1 joins the team. Customer-service savvy Matt Baudette has come on board to take Mission: Customer Success to the next level. Matt brought an excellent analytical background, and his primary focus was to elevate the deployment of the customer success platform Gainsight inside Cleo to deliver optimal service to our clients.  A newly created tactical team was responsible for operationalizing Gainsight, while a few more CSMs were hired and assigned to our larger clients to ensure consistency.  Establishing a quarterly meeting rhythm allowed the team to share ongoing learnings and collaborate on solutions to help our clients get the most out of their investment in the Cleo platform.

December 2019 - It had been quite the whirlwind since we embarked on finding the right partner to acquire EXTOL and my work-life post-sale at Cleo was not at all what I was anticipating. The last 3 years had been extremely challenging and exhausting. I hit the breakpoint where I was questioning why I was still working at there.

Receiving a transmission from thy future captain…”

It would be a-n-o-t-h-e-r 2 years until this realization made any sense to me. It was 2021 and I had just read Simon Sinek’s book The Infinite Game. It was my a-ha moment, as if a cartoon lightbulb went off above my head. I was finally able to understand why my time at Cleo was so draining to me.  This book helped me clearly understand that some companies view the world through theinfinite lens versus a finite lens

While my previous company EXTOL operated through the infinite lens, my time at Cleo taught me what it was like to work for an organization that viewed business through a finite lens – and it was clearly different. This was why I could never fully connect with the leadership team… why every initiative seemed like a battle…. why I felt like an outsider… why the really good ideas took 12-18 months to get implemented after every alternative was attempted and failed… and why I was drained at the end of EVERY DAY.

Prior to reading this book, I did not understand why I felt that way. Now it was crystal clear and truly validated my decision to close that chapter in my life and step-down form the comm as Captain for a different kind of mission. One that would eventually have me focused on helping others who chose to walk on the path of family business leadership.

January 2020 - There were many differences between being 3rd generation family business versus working for a growth organization funded by venture capital. While it was a relief to finally acknowledge that I wanted – and needed – to take a sabbatical, there were still bills to pay. So, what is a former call center representative turned COO to do? 

I decided to dust off my CDL and applied for a job at Masser Logistics driving truck. I traded conference rooms, global zooms and multi-tasking deadlines for open roads and a singular focus. I found myself out on the open road with only other truckers, delivering potatoes (yes, you read that correctly, po-tay-toes) across the US during the first year of the pandemic. It felt so good helping to keep the US food chain supplied while the world was shutting down. And with that handle “Spudman” was born.

“(pssst)…Spudman here… eastbound driver…looking for a road report, any bears…(pssst)?”

The Next Chapter:  A year of trucking. Not part of my original career plan, but just what the doctor ordered. (Thanks “Spock” – you know who you are.)

Read the full blog series:

New Horizons and My “Highly Illogical” Road to here
The Engines are Misfiring, Scotty!
Warp Drive to Acquisition: Teams Tested. Lessons Learned.
Captain’s Blog April 2016: Cleo – To infinity and beyond!
The Finality of Infinity and Beyond


Matthew is a Senior Business Advisor at Compass Point Consulting and provides hands-on consulting & coaching to help family businesses close performance gaps; give owners practical, actionable tools that drive growth; deliver training to develop leaders and position the business for successful ownership transition - all on their terms.

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