and specialist lenders. The team recently completed a large transaction totalling over £60 million to a consortium of borrowers, which is a testament to the calibre of clients we attract and the trust they place in us. Beyond that, it’s been great to see the team expand and develop — we’ve welcomed new trainees and associates who are adding fantastic energy and capability. You’ve mentored many of the firm’s younger lawyers over the years. What advice do you give to those coming up in the profession? Stay curious and stay calm. Every transaction is different, and clients rely on you to bring both technical knowledge and composure. Learn the law, learn from the experience of others, and also learn the business — understand how a deal is structured, where the money comes from, and what the client’s real objectives are. That’s what sets apart a good lawyer from a great one.
Ray, you’ve been with Harold Benjamin for a number of years and have built one of the firm’s most active teams. What do you think underpins that success? : It comes down to four things — relationships, availability, responsiveness, and results. Our clients, whether they are lenders, brokers, developers or investors, trust us to deliver quickly and accurately and to be available when they need to liase with us, We understand that in real estate and finance, timing is everything. Having a team that’s commercially minded and deeply experienced allows us to anticipate issues and find practical solutions that keep deals on track. The secured lending market has evolved significantly over the past few years. What trends are you seeing in 2025? The market has definitely become more sophisticated. We’re seeing increased activity from alternative lenders, private funds, and family offices who are stepping into spaces once dominated by high-street banks. There’s also a stronger focus on bridging finance, refinancing, and portfolio consolidation — all of which require speed and flexibility. At the same time, clients are far more conscious of risk management, so clear documentation, relevant experience and structuring are key. How does the Harold Benjamin team differentiate itself in such a competitive market? Our approach is very personal. We act as partners, not just lawyers. Because our team works across secured lending, investment and commercial real estate, we understand the full lifecycle of a transaction — from acquisition and development through to exit. That gives our clients confidence that we can see the bigger picture, not just the paperwork. We’re also known for our availability — clients know they can pick up the phone and reach us when it matters whether it is early in the morning, late at night or sometimes even at the weekend.
Finally, what’s next for the Secured Lending and Real Estate teams?
Growth — in every sense. We’re expanding our lender base, investing in technology to streamline deal flow, and continuing to strength - en collaboration across departments, especially with our corporate, banking and construction teams. The market is dynamic, and so are we. It’s an exciting time to be part of Harold Benjamin.
And when you’re not closing deals?
You’ll probably find me on the golf course or spending time with my family. Balance is important — but so is a good handicap!
Ray’s leadership and strategic approach contin- ue to define Harold Benjamin’s reputation in the secured lending and real estate sectors. His em- phasis on client service, commercial insight, and team development embodies our firm’s values of teamwork, empathy, and commitment — and sets the tone for the next generation of lawyers and leaders at Harold Benjamin.
What have been some of the team’s recent highlights or notable transactions?
ray.oshry@haroldbenjamin.com
We’ve advised on several multi-million-pound refinancing and development deals this year, including facilities with major international banks
Connect with Ray
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THE LEGAL CORNER MAGAZINE | ISSUE 13 DECEMBER '25 HB
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