For the better part of three decades, private equity firms have looked to Willkie Farr & Gallagher LLP’s Jeffrey Poss for legal advice on a range of deals from M&A and minority investments to in- and out-of-court restructurings and everything in between.

He is a partner in the firm’s corporate and financial services department, co-chair of its private equity group and a member of the executive committee. He is a go-to adviser for many of Willkie’s longtime clients including Aquiline Capital Partners LLC, Genstar Capital LLC and Warburg Pincus LLC, as well as their portfolio companies.

Poss advises companies in all phases of the business lifecycle as evidenced by his 2019 deal sheet, which included more than 50 deals in the upper middle market.

He is the private equity dealmaker of the year for The Deal’s 2020 Middle Market Awards.

“Dealmaking in 2019 was a continuation of the PE bull market we’ve seen for the past several years – a highly competitive environment with high multiples, and further consolidation in the financial services industry, my principal area of focus,” Poss said.

In 2019, for instance, he led a Willkie team that advised Genstar on the sale of a stake in registered investment adviser Mercer Advisors Inc. to Oak Hill Capital Partners LP and was part of the legal effort when Carrick Capital Partners LLC sold a majority stake in Axiom Global Inc. to Permira, both announced in September. In August, he also advised Genstar in its acquisition of a majority stake in automotive software company OEConnection LLC from Providence Equity Partners LLC.

Aquiline Capital is also another regular client of Poss. Among the 2019 highlights, Poss provided legal advice to Aquiline in its July acquisition of CoAdvantage Holdings Inc., which provides human resource software for the middle market, from Morgan Stanley Capital Partners.

In May he advised Aquiline portfolio company Covius Holdings Inc., which provided tech solutions to lenders and other types of financial services, in a strategic new investment by mortgage REIT New Residential Investment Corp. Soon after, he was part of the Willkie team that advised Covius on its acquisition of a variety of businesses including insurance, tax verification and homeowners association tracking units, among others, from mortgage solutions provider Chronos Solutions LLC.

The Covius deal was just one of a number of add-ons for Poss, Willkie and Aquiline. Among them Poss led a team alongside partners in London advising billing and payment solutions provider OSG Billing Services Inc. on its acquisition of London-based Communisis plc and Birmingham, Ala.-based NCP Solutions LLC, in October and November, respectively. In February,  he led a Willkie team for Aquiline in its acquisition of Relation Insurance Inc. from Parthenon Capital Partners LP and Century Equity Partners LLC.

Mandates for Genstar and Aquiline overlapped in 2019 on one of the most influential deals in the financial services industry when the two agreed to sell a stake in Dresher, Pa.-based Ascensus LLC to new investors, led by Atlas Merchant Capital LLC and GIC Pte. Ltd. Ascensus, a savings and loan services company, has subsequently completed a number of add-on deals with Willkie and Poss on the legal team.

“Given my primary focus on the financial services industry, it’s exciting to learn about new fintech, insurtech and other technology-centric companies transforming the industry every day,” Poss said. “Some are improving on the existing asset management infrastructure, others are more disruptive. Counseling investors and companies in this constantly evolving space is exciting and satisfying.”

Looking at 2020 dealmaking, Poss said financial services in particular continues to be a “robust” area despite the overall lull in the first quarter of 2020.

“The stock market volatility like we’ve seen since the outbreak highlights the importance of strong wealth management resources — hence the continued activity in the asset management space — and in the current remote environment, fintech tools and resources have only increased in importance and visibility,” he said.

With lots of dry powder still on the sidelines, ”it’s reasonable to expect a more robust deal environment — both new platforms and tuck-ins for existing portfolio companies — for the remainder of 2020. We are already seeing increased volume,” he added.

A Boston University Law School and University of Pennsylvania graduate, he joined Willkie in 1991 and has been with the firm since, working mainly out of New York.

He was instrumental in the opening of Willkie’s offices in Palo Alto, Calif., in December 2018 and San Francisco in September 2019. He is co-chair of the firm’s PE practice with Neil Townsend.

Editor’s note: This article was sponsored by Willkie Farr & Gallagher.