Thomas Berkley’s career has been built across two very different environments: military service and entrepreneurship. Before becoming the founder of CSM Collective, he spent a decade in the United States Air Force, where discipline, accountability, and structured execution became central to the way he approached work.
After leaving the military, Berkley moved into business, building and scaling several companies and developing experience across sales, marketing, and customer relationships. His website states that his businesses have generated more than $10 million in sales since 2018. He has also received recognition from ClickFunnels, including the Two Comma Club Award and the 10X Award.
His experience eventually led him toward a specific business problem: companies often put substantial effort into acquiring customers but fail to give the same attention to keeping them. That observation became the foundation for CSM Collective.
A Career That Started in the Air Force
Thomas Berkley Cleveland grew up in Cleveland, Ohio, and joined the United States Air Force at 18. He spent the next ten years in military service while beginning to develop an interest in business, sales, and marketing.
The experience gave him a working philosophy that remains visible in his business career. Berkley places considerable emphasis on consistency, clear responsibilities, accountability, and repeatable systems rather than relying on short bursts of motivation.
His entrepreneurial education began while he was still serving. According to his website, he studied business and marketing while on active duty and began developing the ideas that would later influence his approach to building companies.
Rather than treating his military career and business career as unrelated chapters, Berkley has carried many of the habits developed during his service into his work as an entrepreneur.
See also: Leading IT Asset Remarketing Services for Sustainable Technology Lifecycle
Moving From Service to Business
Berkley’s transition into entrepreneurship eventually developed into a full-time business career. His website identifies 2018 as a significant starting point for his work building and scaling companies.
Over the following years, he worked across sales and marketing and developed businesses that collectively generated more than $10 million in sales. The results also brought recognition from ClickFunnels.
He received the ClickFunnels Two Comma Club Award after generating more than $1 million through a single sales funnel. He later received the ClickFunnels 10X Award for surpassing $10 million in total sales.
These achievements provide context for his later focus on customer retention. His experience was not limited to one part of a business. It exposed him to the acquisition side of the customer journey and, eventually, to the problems that arise after a sale has been completed.
Experience With Kevin Harrington
Another notable part of Berkley’s professional background was his work with Kevin Harrington, the original Shark from ABC’s Shark Tank and a well-known figure in direct-response marketing.
According to Berkley’s website, he worked directly with Harrington and managed marketing campaigns for clients in the home services sector.
Working around established entrepreneurs and marketing campaigns gave Berkley additional exposure to how businesses acquire customers and generate revenue. It also contributed to his understanding of the difference between bringing customers into a business and creating an experience that encourages them to remain there.
That distinction became increasingly relevant to his own business philosophy.
The Problem Berkley Saw Across Businesses
Customer acquisition tends to receive a great deal of attention. Businesses track leads, conversion rates, advertising costs, sales calls, and revenue generated from new customers.
Berkley noticed a different weakness.
Companies could have effective acquisition systems while still losing customers because there was no clear process for onboarding, communication, progress tracking, or ongoing support. In his view, the result was a gap between winning a customer and keeping that customer.
His website describes this as a structural problem: businesses spend heavily to acquire clients but often invest far less in retaining them.
That observation shaped the next stage of his career.
The Idea Behind CSM Collective
Berkley founded CSM Collective around the role of the Client Success Manager.
A Client Success Manager works with paying customers after the sale, helping them understand the service, stay engaged, reach agreed goals, and maintain a relationship with the company. The role can be particularly relevant to online businesses such as agencies, coaching companies, consulting firms, and SaaS businesses.
CSM Collective was designed to address two sides of the same issue.
For businesses, the program provides trained Client Success Managers who can take responsibility for customer relationships and retention. For professionals, it provides training and placement support for people interested in developing a career in client success.
The company says it has trained, certified, and placed more than 100 Client Success Managers into online businesses.
Why Retention Became a Central Theme
Berkley’s approach to entrepreneurship is strongly connected to customer retention.
A business can generate substantial revenue from new sales, but high churn can undermine that growth. If customers leave quickly, the company has to keep replacing them simply to maintain its existing revenue level.
A dedicated client-success function addresses the period after the sale. It can help businesses establish better onboarding, maintain communication, monitor customer progress, identify problems earlier, and create a clearer path toward renewals.
Berkley’s philosophy is reflected in his view that businesses should pay closer attention to how long they keep their customers rather than focusing only on how many new customers they acquire.
This perspective is central to the business model behind CSM Collective.
Building a Business Around a Specific Skill
One of the more distinctive aspects of CSM Collective is its focus on a specialized business role rather than general entrepreneurship training.
The company trains people specifically for Client Success Manager positions. The program is also built around placement, meaning the goal extends beyond teaching the responsibilities of the role.
For Berkley, developing a skill has greater value when that skill can be applied inside an operating business.
CSM Collective states that its placement model connects certified CSMs with online businesses, particularly companies generating at least $35,000 per month.
That approach connects Berkley’s experience as a business operator with his interest in creating professional opportunities for people who want to work remotely.
The Influence of Military Discipline
Military service remains a visible influence on Berkley’s approach to business.
His website repeatedly emphasizes discipline and consistency. The principle is straightforward: businesses become easier to manage when responsibilities are clearly defined and important processes do not depend entirely on the founder’s personal involvement.
This philosophy also affects the way he views growth. Instead of building a company around constant hustle, Berkley emphasizes systems that allow teams to operate consistently.
For a growing business, this can be particularly useful in areas such as customer onboarding, communication, account management, and retention. Each of these functions becomes harder to manage informally as the customer base expands.
From Entrepreneur to Educator
Berkley’s role has expanded beyond building companies. Through CSM Collective, he also teaches a specific approach to client success and helps prepare professionals for CSM positions.
That creates a different kind of entrepreneurial role. Instead of simply operating a business, Berkley is developing a framework that other businesses and professionals can use.
His career therefore combines several areas of experience: military leadership, entrepreneurship, sales, marketing, customer retention, and professional training.
The common thread is practical execution.
What His Career Says About Business Growth
Berkley’s career offers several lessons for business owners.
Retention deserves its own strategy
Customer retention should not be treated as an accidental result of good service. Businesses can create dedicated processes and assign responsibility for maintaining customer relationships.
Experience can reveal overlooked opportunities
The idea behind CSM Collective came from a problem Berkley encountered repeatedly while building and working with businesses. Identifying the same problem across different companies helped him recognize an opportunity for a specialized service.
Systems become more valuable as a company grows
A founder can personally manage a small number of customers. That becomes increasingly difficult as a company expands. Processes, documentation, and dedicated roles can help maintain consistency.
A career can evolve through different industries
Berkley’s move from military service to entrepreneurship and then into professional training demonstrates how experience from one field can influence work in another.
The Direction of CSM Collective
CSM Collective remains the central focus of Berkley’s current business work. The company trains and certifies Client Success Managers, places them with online businesses, and focuses on helping those businesses improve retention and customer lifetime value.
The model reflects the issue Berkley identified through his years of business experience: acquiring a customer is only one part of building a sustainable company.
The work that follows the sale can determine whether that customer remains satisfied, achieves the expected result, renews, and recommends the business to others.
For Berkley, that realization became more than an observation. It became the basis for his next company.
Thomas Berkley’s Entrepreneurial Path
Thomas Berkley entrepreneur story has developed through several distinct stages. His ten years in the Air Force gave him a foundation in discipline and accountability. His years in business gave him experience in sales, marketing, and company growth. His work with established entrepreneurs expanded that experience, while his own companies gave him a close view of the challenges businesses face after acquiring customers.
CSM Collective brought those experiences together.
Rather than building another company focused primarily on acquiring leads or increasing sales, Berkley chose to concentrate on the customer relationship that follows the sale. His work now centers on helping businesses retain clients while preparing professionals for specialized Client Success Manager roles.
That focus gives his current career a clear connection to the lessons gathered throughout his earlier work: build systems, measure results, assign responsibility, and create businesses that can continue to perform as they grow.
Author Bio
Business and entrepreneurship writer covering founders, emerging companies, leadership, sales, marketing, and business growth strategies. With a focus on research-based content, the author explores the experiences and ideas behind entrepreneurs and the companies they build.
