Saving creditors from losing out on consumer debts, Cherrywood Enterprises, LLC pioneers debt portfolio buying. Committed to helping financial institutions recover their charged-off receivables, this organization upholds all the required knowledge and experience to aid them. With a large clientele, Cherrywood continues to help financial institutions transact safely and efficiently. As a debt buyer, this firm specializes in purchasing delinquent debts from original creditors.
Having been honored as one of the “Most Influential Companies of the Year 2025” by The CEO Views, we have had the pleasure of talking with Cherrywood’s CEO, Craig M. Geisler. In our conversation with Craig, he took us on an outstanding journey of the company becoming the leading debt portfolio purchaser.
Reimagining Debt Solutions
Before joining Cherrywood, Craig worked for two debt buyers. This allowed him to closely observe where those companies fell short in client relations. Recognizing these shortcomings, Craig decided to establish his own company, determined to correct the mistakes he had witnessed. He sought to build a business guided by passion and integrity, aspiring not just to succeed but to set a new standard in the industry.
An Overview of Cherrywood Enterprises
Cherrywood Enterprises operates with the mission to revolutionize the debt industry. With its team of seasoned professionals, the company helps lenders recover their charged-off and delinquent debt while offering debtors a way to financial recovery. Building on the principles of integrity, transparency, and empathy, Cherrywood commits to ethical debt collection practices, treating each individual with understanding and respect. The company purchases charge-off debt portfolios from banks, credit unions, auto lenders, and commercial lenders. With its network of attorneys worldwide, Cherrywood tries to collect on these accounts.
The firm takes pride in its capability to customize solutions that address the unique needs of creditors and debtors.“Our expert negotiators work diligently to find reasonable and sustainable resolutions, helping debtors get back on their feet while providing creditors with a fair return on their investments,” shared Craig. By deploying data-driven strategies and leveraging advanced technology, Cherrywood efficiently assesses debt opportunities. Moreover, the company goes beyond just being a debt buyer; it is a partner in progress that helps build a robust and financially secure future for all parties involved.
The Six Pillars of Character
Cherrywood has its six core objectives ingrained in all its operations, namely the “6 pillars of character.” Built on these beliefs, Craig aims to run the company through trustworthiness, respect, responsibility, fairness, caring, and citizenship. Let us dive deep into understanding these pillars.
The first pillar is ‘Trustworthiness,’ which includes maintaining honesty, integrity, promise-keeping, and loyalty. The business, with its deep knowledge and experience, wins client trust.
‘Respect’ is the second pillar, on which Cherrywood exercises courtesy, non-violence, tolerance, and autonomy in its service delivery and operations. It treats individuals and businesses with respect and assures to help.
By integrating ‘responsibility’ as the third pillar of character in its work environment, the company encourages employees to fulfill their duty with accountability, pursue excellence, and develop self-restraint. Its reputation and success history with clients speaks for itself.
‘Fairness’ is the fourth pillar of character that Cherrywood has incorporated into its operations and management. The company maintains fair treatment of all by allowing openness, consistency, and impartiality in its work environment.
Cherrywood values the ‘caring’ approach in its debt buying operations. By encouraging kindness, compassion, and empathy among its workforce, the company considers debtors’ well-being throughout the recovery process.
Last but not least, with ‘citizenship,’ the firm ensures civic virtue, lawfulness, and common good in serving the community.
Bringing Home the Bacon
To ensure financial institutions are given “top dollar for charged off receivables” of consumer debt portfolios, Cherrywood’s top-notch underwriters go through each portfolio and sample documents carefully. The company looks at everything within the portfolio to make sure it is not missing anything. After completing the review, the firm feels it has exhausted all its efforts to review each file to maximize the offer to lenders. Additionally, with its legal approach, Cherrywood enables itself to obtain judgments and work with the debtor for many years to come.
Winning Competitive Edge
Besides its six pillars of character, Cherrywood has other strategic approaches that enable the company to serve its purpose in a competitive market environment. The company strives to offer the best pricing in the industry when purchasing portfolios. Along the way, it also aims to keep the lender’s name in good standing. Also, hiring ethical attorneys who the company has worked with for over a decade has helped it win a competitive edge.
Strategies to Put Funds Back in 14 Days
Cherrywood has been operating for almost 20 years in the industry. With such extensive operating experience, the company has experienced both the good and bad market trends, so it knows what to expect. With its team of underwriters who review the spreadsheets and documents, Cherrywood ensures it offers the most aggressive pricing in the industry. So, what it boils down to is industry knowledge and a desire to be the best in the industry.
Technological Integration in Service Delivery
Technology is the cornerstone of every business operating in today’s competitive market. With technological integration, enterprises are reaching the stars in their operations and services, and Cherrywood is no exception. The company leverages various sources of technology in its business, from Microsoft to its in-house technology. The company utilizes Microsoft Word and Excel to be able to help analyze the portfolios.
Cherrywood also uses its own technology in reviewing the portfolios. It helps in determining a range of what the company thinks a portfolio is worth, based on age, year, and model of vehicles, geographic information, reviewing sample documentation for any pitfalls that the company may encounter in the legal process, and its own history of performance on different types of portfolios.
Embodying Influence
When asked about the ways Cherrywood influences industry standards and emerges as an influential company, Craig once again emphasized the role of its six pillars of character. With these pillars ingrained in organizational operations, the company ensures the successful delivery of world-class client services. “It’s easy to buy debt portfolios, but to be able to do so year after year, and earn the trust of so many banks, credit unions, and auto and commercial lenders, well, it says something about our reputation and how we go about our business,” shared Craig.
Cherrywood puts its lender’s reputation first and does not want the debtors to go back to the lenders and complain about their interaction with the company. Craig believes it takes one complaint to ruin a reputation, and Cherrywood takes its reputation very seriously. With consistency for over a decade, the company has earned a general respect from lenders who want to do business with Cherrywood. This is because the company has managed to influence the industry standards significantly.
Devising Future Plan
After building a reputation of consistency over the years, Cherrywood Enterprises is keeping its eye on establishing a future of expansion, compliance, and growth. First of all, the company will continue to monitor industry standards and the changes in state laws to ensure it complies with any new changes in the regulatory landscape of the finance industry. Secondly, it intends to continue to expand into new areas as it learns more about the laws and licensing requirements that each state has, in addition to learning about post-judgment remedies. This means staying on top of the industry, so the company can sidestep any potential landmines. Lastly, Cherrywood strives to be the best in its industry by using the same six pillars of character that it commenced its journey with.
