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After completing his undergraduate at Harvard University and then going on to Columbia Law School, Ian Sterling began his legal career in 1997 at Milbank LLP. He later was a mid-level associate at Cadwalader, Wickersham & Taft LLP, where he was introduced to and focused heavily on structured finance in the run-up to the financial crisis.
“After two decades in the structured finance industry and having gone through the financial crisis, there’s hardly a complex transactional issue I haven’t seen. As a structured finance lawyer, there’s not much that intimidates me,” he proclaims. It was a natural transition for him to transfer from Cadwalader to Barclays, which was one of his biggest clients at the time. In the years leading up to the crisis, many big investment banks were structuring residential mortgage-backed securities and Barclays had jumped on the bandwagon.
“I was there from 2005 until 2014, and it was really a pure structured finance experience with a big dose of M&A right in the middle,” Sterling says, referring to Barclays’ acquisition of Lehman Brothers in 2008.
“I think the best transactional lawyers are structured finance attorneys because they’ve seen everything, and structured finance is so interdisciplinary.”
Ian Sterling
In 2015, after the financial markets had relatively recovered from the crisis, Sterling left Barclays for an opportunity at JPMorgan Chase & Co., a market leader in the structured finance space. And in February 2022, Sterling left JPMorgan to go to Flagstar Bank, where he was hired as a securitization attorney.
“My experience at Flagstar is much more varied and broad. I’m now more of a commercial lending lawyer across a bunch of product types—basically, anything transactional that hits my desk, whether it’s loans, securities, or anything in between, I can do,” he says. “I think the best transactional lawyers are structured finance attorneys because they’ve seen everything, and structured finance is so interdisciplinary.”
In the twenty-five years of experience he gained working in structured finance at big banks, Sterling went into his current role as senior vice president and associate general counsel at Flagstar with plenty of examples of leaders—some good and some not so good.
“There are a lot of people in my professional network who I would consider mentors, but, in retrospect, I wish I’d had even more,” he reflects. “You see a lot of leaders when you work in a big bureaucratic investment bank with a bunch of managers, and you can learn a lot about good leadership. But you also learn a lot about bad leadership or people who make terrible managers.”
Sterling went into his current leadership role at Flagstar knowing exactly the type of leader he wanted to be: one with integrity and one who always does the right thing for the firm. In fact, one of the things he’s most proud of is the mentorship he’s offered to junior staff.
“What I’m most proud of is identifying those junior employees who might be a bit disaffected or overlooked and helping them obtain meaningful opportunities for career advancement,” he says. “That happens with a lot of junior employees; no matter who they are, they can fall through the cracks because many managers don’t prioritize retaining them.”
“You’ve got to keep your people. Spend a little bit more time keeping them in the information loop, showing you’re interested and vested in their advancement, creating opportunities, and making sure they feel engaged and a part of the team.”
Ian Sterling
Mentorship and a focus on retention, in Sterling’s opinion, are very important attributes of the best managers. “If your people leave, that naturally causes problems, whether it’s a dip in morale or wasted resources and energy on trying to fill job openings,” he explains. “Retaining talent is important to any organization, but people in senior management sometimes lose sight of that fact. You’ve got to keep your people; spend a little bit more time keeping them in the information loop, showing you’re interested and vested in their advancement, creating opportunities, and making sure they feel engaged and a part of the team. Otherwise, they’ll leave.”
The advice that Sterling offers to junior-level professionals is only an extension of that sentiment. “You really can’t underestimate the value of your professional network. The strong connections in your personal and professional networks will will help navigate through your career,” he says. “Your reputation as a professional is paramount. Every day you spend at work is an opportunity to be building your brand, so you’ve got to let people know who you are, what you can do, and how you are a valuable asset to the organization.”
“Ian leaves nothing to chance. He is very disciplined, methodical and above all, practical, in how he assesses risk and solves problems for his company. He is a consummate team player.”
