A CFO Across Three Ownership Structures
Michael Culhane has held the chief financial officer seat in companies owned three different ways: publicly traded, private-equity-backed, and family-held. He has held those roles on both sides of the border, and in retail, industrial distribution and technology-enabled services.
He joined Hudson’s Bay Company as Senior Vice President and Chief Financial Officer in 2009 and served as Chief Financial Officer from 2012 to 2014, across a North American retail group of roughly $7 billion in revenue operating Hudson’s Bay in Canada and Lord & Taylor, Saks Fifth Avenue and Saks Off Fifth in the United States. He was Chief Financial Officer of Fareportal, a global online travel company operating CheapOair and OneTravel, from 2015 to 2016, and founded TMA Group, a CFO advisory practice, which he built to a team of ten before stepping away in 2018.
From 2018 to 2020 he was Chief Financial Officer of Uline, the family-owned industrial and packaging distributor operating across the United States, Canada and Mexico, where he expanded the financial planning function, scaled credit and collections to support enterprise growth, and recruited the company’s first treasurer. He returned to Hudson’s Bay as Chief Financial Officer of the holding company for Saks Fifth Avenue, Saks Off Fifth and Hudson’s Bay from 2020 to 2024, and then as Chief Operating Officer and Chief Financial Officer from 2024 to 2025, with responsibility spanning finance, logistics, store operations and legal. Most recently he was Senior Vice President, Finance at The Fedcap Group, a nonprofit of roughly $400 million operating across the United States, Canada and the United Kingdom.
The three ownership structures matter more than the sector label. A public company sells under disclosure obligations and a board that answers to shareholders. A sponsor-owned business sells on a fund clock, with a capital structure built for the exit rather than for the operation. A family-owned business sells once, usually with the owner still running it, and with considerations that never appear in a model. Each produces a different transaction, a different diligence posture, and a different definition of what a good outcome looks like.
The Practice
Windsor Drake represents founders and owners in the sale of their companies. Michael Culhane advises on the mandates where the risk to the outcome sits in the operations and the finance work rather than in the pitch. That risk is the same in software as it is in distribution, which is why the role is defined by function rather than by sector.
His contribution is deliberately narrow and deliberately practical. Most sell-side advice concentrates on the period before a price is agreed. He works on the period after it, which is where a founder with rollover equity or an earnout still has most of the money at stake and almost none of the leverage.
That is the seat he has sat in. A CFO who has closed and integrated transactions knows which commitments in a purchase agreement are straightforward to honour and which ones quietly require a function the company does not have. Sellers agree to both in the same afternoon, and only discover the difference in the ninety days after signing.
Where the Expertise Sits
Four areas carry most of the post-signing risk in a founder-led sale. Each of them is finance work rather than negotiation, and each of them is cheaper to solve before a buyer is contacted than after.
Closing readiness and the transition
A transaction is not finished when the price is agreed. It is finished when the business has actually transferred: systems, people, vendor relationships, leases, inventory and the reporting the new owner needs from day one. Buyers form their view of a management team during that period, and in structures where the seller stays on, that view has money attached to it.
The work is unglamorous and it is the difference between a clean close and a retrade. Preparing the company so the transition is a plan rather than an improvisation is the single most reliable way a seller protects the value already negotiated.
Rollover equity and earnouts
When a founder rolls equity or accepts an earnout, part of the purchase price is converted into a claim on how the business performs under someone else. The headline number becomes an estimate. What determines the actual outcome is how the earnout is measured, who controls the inputs to that measurement, and whether the operating plan the buyer intends to run is the same one the earnout was written against.
Those questions are financial and definitional, not legal. An earnout tied to a metric the buyer can influence through allocation, capital spending or accounting policy is a different instrument from one tied to a metric that is hard to move. Understanding the difference before signing is worth considerably more than arguing about it afterward.
Divestitures, carve-outs and wind-downs
Selling part of a business is materially harder than selling all of it. A carve-out has to be separated from shared systems, shared services, shared vendor contracts and shared people, and the standalone financial statements a buyer will diligence usually do not exist until someone builds them.
The same discipline governs the disposals that sit around a transaction: locations that are not going with the deal, inventory that has to be converted to cash on a schedule, and leases that have to be settled, assigned or handed back. Those are execution problems with real cash consequences, and they are frequently the part of a transaction nobody has priced.
Working capital, inventory and the peg
In inventory-carrying businesses, the working capital adjustment is where a meaningful amount of purchase price is won or lost after signing. The peg is set from a historical average that may not reflect how the business actually cycles, and inventory that is carried at cost is not always inventory that is worth cost.
Sellers who have not modelled the peg against their own seasonality, and who cannot defend their inventory valuation with more than a system report, hand the buyer a post-closing adjustment. It is one of the few places in a transaction where preparation converts directly into cash retained.
Most of what a seller negotiates is protected or lost in the ninety days after signing, not in the weeks before it. That period is an operating problem, and it should be planned like one.
The Zellers Divestiture
In January 2011, Target Corporation agreed to acquire leasehold interests in up to 220 Canadian store locations from Zellers Inc., a subsidiary of Hudson’s Bay Company, for C$1.825 billion. Target completed its selection in two stages, taking 105 leases in May 2011 and a further 84 that September, for a final total of 189 locations. Leases Target did not take were sold to other retailers or returned to landlords.
Michael Culhane was Senior Vice President and Chief Financial Officer of Hudson’s Bay Company when that agreement was reached, and Chief Financial Officer through the period that followed. The lease sale was the beginning of the work rather than the end of it. Alongside the transaction he oversaw the orderly wind-down of 283 Zellers stores and 150 Fields locations: closures sequenced against the lease transfers, inventory converted to cash across a national chain, and the settlement of every lease that did not go to Target.
The relevance to a founder-led sale is one of proportion rather than scale. A $20 million transaction has the same categories of post-signing work as a billion-dollar one: inventory to convert, obligations to settle, systems to separate, and a schedule that somebody has to own. The difference is that the larger company has a department for it and the founder-led company usually has the founder.
Capital Markets and Acquisitions
Two further transactions from the same period put the same discipline at the top of the capital structure.
In November 2012, Hudson’s Bay Company returned to the public markets with a C$365 million initial public offering on the Toronto Stock Exchange, priced at C$17 per share and supported by an international investor roadshow. In July 2013, the company agreed to acquire Saks Incorporated at US$16 per share, a transaction valued at approximately US$2.9 billion including debt, financed through a combination of equity and debt. Michael Culhane was Chief Financial Officer for both.
In his second period at the company, from 2020, he led debt financings and asset sales through the pandemic and secured capital to fund the group’s e-commerce investment. A founder selling a business rarely needs an IPO. What transfers is the discipline: knowing what a diligence process actually tests, and what a capital provider or an acquirer will require in writing before money moves.
Career Record
Windsor Drake publishes the record rather than paraphrasing it. Credentials that cannot be checked are not credentials, and a firm asking to represent the largest transaction of an owner’s life should expect to be verified rather than believed.
- Role Senior Advisor, Windsor Drake · transaction execution, closing mechanics and CFO advisory on founder-led sale mandates
- Hudson’s Bay Company Senior Vice President and Chief Financial Officer, 2009 to 2012 · Chief Financial Officer, 2012 to 2014 · Chief Financial Officer of the holding company for Saks Fifth Avenue, Saks Off Fifth and Hudson’s Bay, 2020 to 2024 · Chief Operating Officer and Chief Financial Officer, 2024 to 2025
- Uline Chief Financial Officer, 2018 to 2020 · family-owned industrial and packaging distribution across the United States, Canada and Mexico
- Fareportal Chief Financial Officer, 2015 to 2016 · global online travel, B2C and B2B
- TMA Group Founder and President, 2016 to 2018 · CFO advisory practice built to a team of ten
- The Fedcap Group Senior Vice President, Finance · nonprofit of roughly $400 million across the United States, Canada and the United Kingdom
- Transactions C$1.825 billion Zellers lease divestiture to Target Corporation and the wind-down that followed · C$365 million initial public offering, Toronto Stock Exchange · approximately US$2.9 billion acquisition of Saks Incorporated
- Education B.B.A. in Accounting, University of Wisconsin-Madison
- Focus Transaction readiness, divestitures and carve-outs, working capital and inventory, earnout and rollover-equity structures, post-signing transition
A Confidential Conversation
Owners contact Windsor Drake at very different points: holding an unsolicited offer, a year out from a process, or simply wanting to understand what a buyer would find. Michael Culhane advises on those mandates alongside the firm’s managing director.
Inquiries are handled discreetly. If a sale is not the right answer, the firm says so. Request a conversation, or read how the firm runs a process in the sell-side process.
Appointments and dates on this page reflect Michael Culhane’s own account of his career. Transaction figures are stated as reported by the parties at the time: the Zellers lease agreement at C$1.825 billion and 189 locations per Target Corporation; the Toronto Stock Exchange offering at C$365 million as completed; the Saks Incorporated acquisition at approximately US$2.9 billion including debt. Nothing on this page is an offer, a solicitation, or a representation as to the outcome of any transaction.
