ByJohn A
Thomas Berkley Cleveland From Air Force Veteran to Entrepreneur and Client Success Founder
For many entrepreneurs, the path to building a business begins with a single idea.
For Thomas Berkley Cleveland, the journey began much earlier with military service, years of discipline, and a growing interest in entrepreneurship.
Today, Berkley is a Cleveland, Ohio-based entrepreneur, United States Air Force veteran, and founder of CSM Collective. His professional journey has taken him from serving in the Air Force to building and scaling businesses and, more recently, developing a company focused on client success and remote career opportunities.
His story reflects a broader evolution in modern entrepreneurship: moving beyond simply acquiring customers and focusing on what happens after the sale.
From Military Service to Entrepreneurship
Long before the name Thomas Berkley became associated with entrepreneurship, Berkley was serving in the United States Air Force.
He joined the Air Force at 18 and ultimately spent ten years in military service.
That experience gave him a foundation built around discipline, accountability, consistency, and structured execution.
At the same time, Berkley developed an interest in business.
While serving, he studied areas including sales and marketing and began preparing for a future outside the military.
When he left the Air Force in 2018, he made the transition into entrepreneurship.
There was no established company waiting for him.
He began building from the ground up.
Building and Scaling Businesses
Berkley’s years in entrepreneurship exposed him to many sides of running a business.
Marketing.
Sales.
Customer acquisition.
Business systems.
Scaling.
And, eventually, customer retention.
According to his professional biography, Berkley has built and scaled multiple companies generating more than $10 million in combined lifetime sales.
His entrepreneurial work also received recognition from ClickFunnels.
Among those recognitions were the Two Comma Club Award, associated with generating more than $1 million through a single sales funnel, and the 10X Award following more than $10 million in total lifetime sales across his businesses.
For Berkley, those milestones represented more than revenue numbers.
They reflected years of learning how to build offers, create marketing systems, generate customers, and develop businesses capable of scaling.
Working With Kevin Harrington
Another significant part of Berkley’s entrepreneurial background was his work with Kevin Harrington, the original Shark associated with ABC’s Shark Tank.
Through American Entrepreneur, Berkley managed marketing campaigns for home-service business clients connected with Harrington’s business.
The experience provided another perspective on entrepreneurship and business growth.
Working with businesses at different stages meant seeing firsthand how marketing, sales, operations, and customer experience interact.
It also reinforced an important lesson.
Generating a sale is only one part of building a successful business.
The customer experience that follows can be just as important.
The Question That Changed the Direction
As Berkley gained more experience, he began noticing a recurring challenge among growing businesses.
Companies could become very good at acquiring customers.
But acquisition was only the beginning.
Once a customer purchased, someone still needed to help them get started, communicate with them, monitor their progress, address problems, and keep the relationship moving forward.
Without that structure, businesses could lose customers even after investing significant resources to acquire them.
That observation became increasingly important to Berkley’s entrepreneurial philosophy.
The question was no longer simply:
How do you get more customers?
It became:
How do you help the customers you already have succeed?
The Creation of CSM Collective
That question ultimately led to CSM Collective.
Founded by Thomas Berkley, CSM Collective focuses on training and certifying Client Success Managers and connecting qualified professionals with online businesses seeking client-success support.
The concept addresses two sides of the market.
Businesses need people who can take ownership of the post-sale customer relationship.
Professionals need opportunities to develop specialized skills that can translate into remote careers.
CSM Collective was created around that intersection.
Its approach focuses on areas such as onboarding, communication, customer engagement, progress tracking, accountability, and retention.
The objective is to make client success a defined business function rather than something left entirely to a founder or sales team.
Why Client Success Matters
Customer acquisition is highly visible.
Businesses can measure leads, sales calls, conversion rates, advertising costs, and revenue.
Customer success is different.
Much of its impact occurs after the customer has already purchased.
A client may need help understanding the next step.
A customer may stop engaging with a program.
An agency client may have questions about deliverables.
A coaching client may struggle to implement a strategy.
These situations can affect whether a customer continues the relationship.
A Client Success Manager provides a dedicated point of responsibility for that experience.
Rather than waiting for customers to raise problems, the role can involve proactively checking progress, identifying obstacles, maintaining communication, and helping customers move toward their intended outcomes.
That is the business function Berkley has chosen to build around.
Thomas Berkley Cleveland and the Importance of Systems
The phrase Thomas Berkley Cleveland represents more than a geographic connection.
It also provides context for where Berkley’s current entrepreneurial chapter is taking place.
Based in Cleveland, Ohio, Berkley has brought the systems-oriented mindset developed through his military and entrepreneurial experiences into CSM Collective.
His approach emphasizes repeatable processes rather than relying entirely on individual effort.
For client success, that can mean having defined onboarding procedures, scheduled communication, measurable milestones, and clear ownership of customer relationships.
The underlying philosophy is straightforward.
If customer success matters to a business, it should have a system behind it.
Creating a Remote Career Path
CSM Collective isn’t focused solely on businesses.
The company also addresses the professional side of client success.
Remote work has opened opportunities for professionals in areas ranging from marketing and sales to operations and customer experience.
Client success is another field where communication and relationship-management skills can be applied remotely.
The role can be particularly relevant for people who are organized, comfortable communicating with customers, capable of solving problems, and focused on helping others achieve specific outcomes.
Through its training and placement model, CSM Collective aims to help professionals develop those capabilities into a specialized career.
According to the company, more than 100 professionals have been trained and placed with online businesses.
From Selling to Serving
One of the central ideas behind Berkley’s current work is the shift from viewing a sale as the end goal to viewing it as the beginning of a customer relationship.
A company can have excellent marketing.
It can have an effective sales process.
It can generate a steady flow of new customers.
But sustainable growth also depends on what happens afterward.
Customers want communication.
They want clarity.
They want results.
And they want to know that the company they purchased from is invested in helping them move forward.
Client success exists at that intersection.
It connects the business with the customer after the transaction and creates a structured process for managing that relationship.
The Influence of the Air Force
Berkley’s military background remains an important part of his story.
Ten years in the Air Force provided an environment where discipline, responsibility, teamwork, and procedures were central to daily operations.
Those principles can also be seen in his approach to entrepreneurship.
Rather than treating business success as a matter of individual effort alone, Berkley emphasizes the importance of systems and accountability.
That philosophy has followed him from entrepreneurship into his work with CSM Collective.
The idea is that businesses should create processes that can be followed consistently, measured, and improved.
What Comes Next for Thomas Berkley?
In 2026, Berkley’s focus is centered on CSM Collective and the continued development of client success as a professional function within online businesses.
His entrepreneurial journey has moved through several distinct stages.
Military service provided the foundation.
Entrepreneurship provided years of experience in sales, marketing, and business growth.
Working with established entrepreneurs provided another perspective on scaling.
And CSM Collective brought those experiences together around customer retention and client success.
The common thread is systems.
Build a process.
Create accountability.
Measure outcomes.
Improve the customer experience.
And continue learning.
Thomas Berkley Cleveland: The Next Chapter
The story of Thomas Berkley Cleveland is ultimately a story of professional evolution.
From joining the Air Force at 18 to spending a decade in military service, from transitioning into entrepreneurship in 2018 to building businesses generating millions in sales, Berkley’s career has continued to develop around new challenges.
His current chapter is focused on a problem that sits on the other side of customer acquisition.
How can businesses do a better job of helping the people who have already trusted them?
Through CSM Collective, Berkley is building a business around that question while creating a potential career path for professionals interested in remote client success.
The principle behind the work is simple:
Acquiring a customer starts the relationship. Helping that customer succeed is what develops it.
For the Cleveland entrepreneur, that idea has become the focus of his next stage of business building.
About Thomas Berkley
Thomas Berkley is a Cleveland, Ohio-based entrepreneur, United States Air Force veteran, and founder of CSM Collective. He entered entrepreneurship after completing ten years of military service and has since built and scaled multiple businesses. His professional background includes ClickFunnels recognition and work with Kevin Harrington’s business network. Today, Berkley focuses on client success, customer retention, and developing remote opportunities through CSM Collective.
Learn More
To learn more about Thomas Berkley’s background, entrepreneurial journey, and current work, visit his official website at thomasberkley
