Robert E. Massengill
MANAGING DIRECTOR
Bob Massengill is a co-founder of Pilot Hill Advisors and has advised owners and CEOs on investment banking transactions throughout his business career. These transactions have included sell-side and buy-side M&A advisory work, leveraged and non-leveraged minority ESOPs, second-stage ESOPs, 100% ESOPs, sales of ESOP companies, acquisitions by ESOP clients and ESOP terminations.
Bob serves as a board member of Kesslers Diamond Company a 100% ESOP-owned diamond retailer. He also served as a director for two ESOP-owned companies that sold to synergistic buyers.
Prior to forming Pilot Hill Advisors, Bob was President and shareholder of SES Advisors and Vice President and shareholder of Menke & Associates. Bob graduated with a Bachelor of Science in Business from Miami University (Oxford, OH) and earned a Master of Business Administration in Finance from the New York University Stern School of Business. He also holds securities industry registrations Series 24, 63 and 79.
James F. Higgins, Jr.
MANAGING DIRECTOR
Jim Higgins is a co-founder of Pilot Hill Advisors and specializes in designing, financing and executing internal buyout transactions for privately-held companies. Jim has advised over 100 companies on management and ESOP buyouts that provide unique financial, tax, strategic and motivational benefits that are distinct from traditional third-party corporate sales.
Jim has held senior corporate finance and advisory positions for 25 years. His specialty in ESOP and MBO transactions began in 2001. Jim's prior employers include Bank of Boston, AT&T and Merck.
Prior to forming Pilot Hill Advisors, Jim was a shareholder at SES Advisors and Vice President at Menke & Associates. Jim received a Bachelor of Science in Finance from Boston College and a Master of Science in Management from Massachusetts Institute of Technology. He also holds Series 24, 63, 79 and 99 securities registrations.
James B. Junker
MANAGING DIRECTOR
Jim Junker joined Pilot Hill Advisors in 2018.
Jim first met the founders of the firm in 2008 when he was advising a client seeking to spin-out from its publicly-traded parent using a leveraged ESOP. Working with Pilot Hill Advisors the transaction was successfully completed and the client continues to prosper as a 100% tax free corporation. In subsequent years, Jim completed several leveraged ESOPs.
Throughout his banking and finance career, Jim led over $4 billion in financing and investment banking transactions including leveraged loans, securitizations, public and private bonds, commercial paper, recapitalizations, mergers and acquisitions and ESOPs buyouts. He has also completed numerous sell-side and buy-side advisory roles in ESOP transactions.
Prior to joining Pilot Hill Advisors Jim worked in corporate and investment banking for some of the top banks in the U.S. including First Chicago, JP Morgan Chase, GE Securities and Wells Fargo. Jim also has considerable experience in the equipment leasing arena.
Jim holds a Master of Business Administration in Finance from the Stephen M. Ross School of Business and a Bachelor of Arts both from the University of Michigan. He also holds Series 24, 63 and 79 securities registrations.
Jim is based in the firm’s Michigan office and will assist in expanding Pilot Hill Advisors’ presence in the Midwest.
Charles Kroll, CPA
MANAGING DIRECTOR
Charles Kroll, CPA, joined Pilot Hill Advisors in 2025.
Charles has extensive experience working with ESOPs, including spending 8 years as Chief Financial Officer of Crystal Flash, Inc., a 100% ESOP-owned company. His experience at Crystal Flash included managing the full annual ESOP process from creating the financial projections used for the annual ESOP valuation, to forecasting and the repurchase obligation, to ensuring the company stayed in full compliance with all ESOP-related laws and regulations. In addition to overseeing Crystal Flash’s accounting and finance departments, Charles also spent time managing human resources and was the corporate treasurer and secretary.
Charles is deeply involved in the ESOP community, including being an active member of the National Center for Employee Ownership (NCEO) and The ESOP Association, where he has presented at conferences and served in leadership roles. Charles was a past Michigan Chapter President of The ESOP Association and a former member of the Executive Committee of the State and Regional Chapter Council. Charles also started and leads a peer ESOP CFO network that has grown to 40+ members and meets quarterly to network and share best practices. Charles also serves as an independent board member for a 100% ESOP company and is actively engaged with the Grand Rapids Chamber of Commerce
Prior to working at Crystal Flash, Charles was the controller at a large, privately-owned tool & die manufacturing company, and prior to that he was a CPA at Plante Moran for 8 years.
Charles received a Bachelor of Arts from Hope College and is a registered CPA in the State of Michigan.
Carl P. Genberg
MANAGING DIRECTOR
Carl Genberg joined Pilot Hill Advisors in 2025 after a lengthy career advising private and public companies on their most important transactions.
Carl was the National Practice Leader for Wells Fargo’s Business Transition Planning team advising business owners on transition alternatives including ESOPs, strategic sales, private equity recapitalizations, management buyouts and family / partner transitions. The team’s charter was both to educate business owners on their options but also aid in the decision-making process through qualitative and quantitative discovery, valuation and proceeds analysis to identify the best option for each client.
Carl also served as co-head of Wells Fargo Securities’ 10-state North Region middle market investment banking and capital markets practice leading sellside and buyside mergers and acquisitions, as well as bank, bond, private credit and equity market transactions. He also managed a $5 billion loan origination, underwriting and servicing portfolio including complex leveraged ESOP financings for Wells Fargo Bank.
Prior to his 17-year career with Wells Fargo, Carl was a sellside M&A investment banker with two middle market boutiques, a financial and operating executive for multiple start-ups and Fortune 500 companies and a management consultant. In these roles, Carldshattuck@oakland-hills.com raised capital and led the successful exits of multiple private companies from the inside giving him a deep appreciation for the challenges faced by client management teams.
Carl graduated with a Bachelor of Arts in Economics and Mathematics from Claremont McKenna College where he was Phi Beta Kappa and a Lowe/Baker Research Scholar.