Derek Pitts is Managing Director and Co-Founder of Cayne Crossing. He has over 18 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 30 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 CFA. He lives with his wife, Brooke, and three children, Caroline, Layton and Laina, in Atlanta, Georgia.
Josh Thomas is Managing Director and Co-Founder of Cayne Crossing. He has over 17 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 he 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.
Paul Dubsky joined Cayne Crossing in 2024 as a Managing Director. Paul has a broad and comprehensive background, including over 20 years of experience in audit and M&A advisory services at KPMG, EY, Grant Thornton, Bennett Thrasher and Frazier & Deeter as well as 12 years in industry at Cox Enterprises. Most recently Paul spent the past 5 years as a Director in Grant Thornton’s national transaction advisory services practice leading buy- and sell-side financial due diligence and quality of earnings engagements on over 100 M&A transactions in the middle and lower-middle market. Paul’s industry experience includes manufacturing & distribution, business services, transportation & logistics, media & communications, hospitality, software, and healthcare.
Paul graduated cum laude from the University of Georgia with a BBA in Accounting. He is a CPA and former CFE. He and his wife, Beth, have four children and one grandchild, and live in Dunwoody, Georgia. Paul’s “why” is centered around faith, family, fitness, and finances.
Prachi Sankalia joined Cayne Crossing as a Director of Tax in 2025. She is a licensed tax attorney and provides tax due diligence, structuring, and related services. Prachi has over 10 years of M&A tax experience serving clients in the mid and lower markets. Her expertise includes due diligence and tax structuring for buy and sell-side transactions across a diverse array of industries such as software & technology, manufacturing & distribution, professional services, food & beverage, and retail. Prachi started her career at PwC in M&A tax and later joined top 10 accounting firm, Forvis Mazars.
Prachi has an LL.M. in Taxation from the Southern Methodist University School of Law, and a J.D. from Washington and Lee University School of Law. She earned her undergraduate degree in Public Relations from the University of Texas at Austin. Prachi lives with her husband Jainan, two children, Yashwin and Roshni, and two cats in Dallas, Texas.
Courtney Reese joined Cayne Crossing in 2025 as a Vice President. She began her career in lower middle market M&A due diligence and, over the past three years, has been involved in acquiring and operating more than 100 small businesses across industries including manufacturing, distribution, retail, home services, and food and beverage.
Courtney is a Certified Public Accountant (CPA) and earned her degree from Drury University, where she was a member of the inaugural women’s triathlon team. She currently resides in Kansas City, Kansas.
Lorraine Calica joined Cayne Crossing as a Vice President in 2025. She began her career in transaction advisory with Big Four firms in the Philippines, where she developed expertise in financial due diligence and business valuation. This foundation later led her to a role in sales strategy and operations at a California-based technology company, where she supported sales leadership in strategic planning and operational decision-making. She subsequently moved to an outsourced professional services firm, where she assisted clients around the world with M&A transactions and valuation engagements.
Lorraine is a licensed Certified Public Accountant in the Philippines and a U.S. Certified Management Accountant. She earned her bachelor’s degree in Business Administration and Accountancy from the University of the Philippines Diliman and holds an MBA in International Corporate Strategy from Hitotsubashi University in Tokyo. Lorraine lives in the Philippines with her husband, Walther.
Ours started back in 2007, when Derek and Josh 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, they had the pleasure (and occasional displeasure) of sharing a 50 square foot office. In these tight quarters, they bounced many business and investment ideas off one another and in late 2010, 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, they continued their professional services careers helping clients buy businesses (ranging from Fortune 500 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 were always drawn to the idea of investing in businesses themselves. In 2017, they 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 them and being partners at separate accounting firms, they realized how different it is when you are on the front lines with your money on the line. They 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, they decided to launch 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.
Let’s talk. We’ll help you understand what’s out there, what’s possible, and how to make your next move a smart one.