Our Story / Team

Navigating a path through the small business landscape.

Back in 2007, we met while working together in the M&A due diligence group of one of the Big 4 accounting firms. Due to a reshuffling of office space and renovations, we had the pleasure (and occasional displeasure) of sharing a 50 square foot office. In these tight quarters, we bounced many business and investment ideas off one another and in late 2010, we decided to go in on our first investment together...a single family rental. Though only one house, this was during the Great Recession – it was a scary time, banks did not want to lend, and there was no end in sight to foreclosures. We did our research, challenged our thesis, and had the encouragement from one another to dive in. After the first investment, we continued to grow our holdings and the experience solidified our conviction that the opportunity in private markets is immense, particularly when they are viewed as risky.

With one side gig in full tow, we continued our professional services careers helping our clients buy businesses (ranging from Fortune 600 companies and renowned Private Equity funds doing billion deals to mom and pop owners looking to purchase local competitors for a few million dollars), but we were always drawn to the idea of investing in businesses ourselves. In 2017, we found the right opportunity with Derek leading the purchase of a logistics company and Josh joining as an investor and advisor. Despite working on over 500 acquisitions between us and being partners at separate accounting firms, we realized how different it is when you are on the front lines with your money on the line. We also learned how important people are to the equation and the value of partnerships. Every business is a collection of partnerships: customers, suppliers, employees and even lenders. Success occurs when everyone is aligned, the business has the right people to execute strategic plans and the money to do it.

So after a year of global change and uncertainty, we decided to start Cayne Crossing in 2021. Breaking from the norm and pursuing your goals of buying, operating, and growing a business can be extremely intimidating and scary. We have spent our careers helping people buy businesses and believe we can help you make your investment a success. A good partner is there to give you encouragement when you need it, advice and tough love on hard decisions, and be a sounding board when you just need to vent. We have been there, we have advised many buyers, and we want to partner with you.

Meet The Team

Derek Pitts

Managing Director & Co-founder

Derek Pitts is Managing Director and Co-Founder of Cayne Crossing. He has over sixteen years of M&A experience with a focus on technology and business services companies in the lower middle market. Derek has experience leading corporate development and has significant expertise in roll-ups as well as carve-out transactions. Prior to Cayne Crossing, Derek was a Transaction Advisory Partner at a top 50 accounting firm based in Atlanta, Georgia. Derek began his career at KPMG where he was a Director in the Deal Advisory practice.

Derek attended the University of Georgia for his undergraduate degree (Finance) and then received his Master of Professional Accounting at the University of Texas at Austin. He is a CPA and CFA. He lives with his wife, Brooke, and three children, Caroline, Layton and Laina, in Atlanta, Georgia.

Josh Thomas

Managing Director & Co-founder

Josh Thomas is Managing Director and Co-Founder of Cayne Crossing. He has over 16 years of M&A due diligence experience across a wide range of industries and client types. The majority of his career has focused on deals in the lower middle market. Prior to Cayne Crossing, Josh was a Transaction Services Partner at a middle market accounting firm in Atlanta, Georgia. Josh began his career at KPMG where we met Derek.

Josh attended Vanderbilt University for his undergraduate degree (Economics) and then received his Masters of Accountancy at UNC – Chapel Hill. He is a CPA and CFA. He lives with his wife and two sons in Atlanta, Georgia.

Chris Williamson

Managing Director

Chris Williamson is Managing Director of Cayne Crossing. Chris has over eight years of experience with a focus on lower middle market M&A transactions on the buy and sell-side. Chris's expertise covers many industries, having worked on transactions in software and technology, business services, manufacturing & distribution, education, retail, franchise & hospitality, financial services, and real estate. Prior to Cayne Crossing, Chris worked in Transaction Advisory at a top 50 accounting firm in Atlanta, GA. Chris began his career in the Audit & Assurance practice at PwC.

Chris attended Georgia Southern University for his undergraduate degree in Accounting and Finance and his Master of Accounting degree. Chris was also a member of the varsity football team. He is a CPA. Chris, his wife Mary Kathryn, his two sons James and George, and their golden retriever Oliver live in Atlanta, Georgia.

Megan Kilpatrick

Director

Megan Kilpatrick joined Cayne Crossing in 2021 as a Director. Prior to joining, Megan was a Senior Manager at Turner Broadcasting (now Warner Media) as part of their Technology Finance team and was a Manager at EY in their Transaction Advisory Services practice in McLean, VA and then in Atlanta, GA.

Megan has a Masters of Accounting from the University of Virginia and a BS in Accounting and Business Administration from Washington & Lee University. She is a CPA. Megan and her husband Will have two boys and live in Atlanta, GA.