Ellie Jackson rises to MD through succession planning

Ellie Jackson was studying makeup and prosthetics for television and film at the London College of Fashion when the pandemic hit in 2020. Her first-choice industry shut down overnight, leaving her career plans in tatters. A primary school friend’s mother—Carla Preston, then managing director at Chingford-based broker Robert Gerrard—was looking for an apprentice. Five years later, Jackson is set to take over the top job herself.

Jackson leaned into an old school motto—”find a way or make a way”—and reached out to family and friends for viable alternatives. That conversation with Preston’s daughter led to an apprenticeship at the commercial and high net worth broker. She completed two apprenticeships and earned the Chartered Insurance Institute’s certificate and diploma in insurance. By last month, at age 28, she had been named Preston’s successor, effective 1 August 2026, ending a 40-year tenure at the firm.

Robert Gerrard, now owned by Jensten Group, employs 21 staff including two apprentices. The broker handles £11m in gross written premium and insures roughly 1,000 UK businesses, specializing in lift and escalator coverage.

“It’s quite surreal when you say it out loud, but a lot has been packed into that five-year journey,” Jackson said in her first interview following the promotion. “I want to be the best managing director possible and I will do anything to work towards that. It’s a huge milestone for me. I don’t take it lightly, but it’s not the end of my journey. I’m really excited about the challenges that are going to come.”

Building a Leadership Profile

Jackson’s path at Robert Gerrard followed a traditional climb—account executive, senior account executive, team leader, sales development manager. But over the last three years, her role expanded beyond day-to-day account handling. She became increasingly involved in conversations about growth, strategy, and the overall direction of the business.

That wider remit let her launch her own initiatives. Last summer, she introduced a customer-focused cyber campaign that pushed insurance take-up among clients from 5% to 15% within a year. She also started The Pipeline Club in 2023 to mentor junior colleagues on lead generation and career progression.

The idea of actually becoming managing director took a clearer shape around 18 months before her appointment. Jensten Group acquired Robert Gerrard in August 2024, joining its schemes and affinities portfolio. “Succession is very much a part of that plan when you sell your business,” Jackson said. “Until then, becoming managing director was certainly an ambition. But there’s a big difference between privately aspiring to something and people actually believing you can do that.”

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Jackson spent years building on her 25-year relationship with Preston—first as her friend’s daughter, then as a colleague—to learn the leadership ropes firsthand. Jensten Group backed her development by enrolling her in its Leading Lights leadership apprenticeship two years ago and connecting her with mentors from the executive committee.

What Comes Next

Jackson is quick to note she won’t simply step into Preston’s shoes. “Succession works well when you don’t come in and pretend to be someone else,” she said. “I’m not Preston. We lead very differently and what I want to do is protect what she’s built because she worked so hard to build it. But I want to lead in my own way and be respected for that.”

Her five-year strategy centers on organic growth and a handful of larger projects. The broker launched its lift and escalator scheme—backed by insurer Chubb—in January 2025. Jackson wants to take that same product into Germany and Italy next, expanding the firm’s international footprint.

She spent time in both countries last year attending trade shows to gauge demand. “In Germany, I was there for 36 hours. I saw 22 clients and created 14 opportunities,” she said. A month later, she spent 24 hours at the equivalent Italian event speaking with insurers and lift companies focused on the sector.

The UK market is reaching capacity. Robert Gerrard now services around 50% of the lift and escalator sector domestically. “You’re only going to grow so much in the UK and a lot of the larger lift companies have either an international parent company, or are based outside the UK,” Jackson explained. “So, if you want to go into that larger corporate world, expanding internationally is naturally the next step.”

The plan calls for launching the scheme in Germany and Italy by 2027 or 2028 at the latest. The business would service those markets from its UK headquarters rather than setting up local offices, supported by a planned increase in its 21-person headcount.

International expansion is only part of the picture. Jackson also wants to explore adjacent scheme opportunities back at home. “Whether that’s a new scheme or additional products to what we’re already doing, that is really the next piece of strategy,” she said, pointing to potential partnerships with suppliers and manufacturers already working with lift companies.

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Being part of the acquisitive Jensten Group opens doors on that front too. While Jackson said she is open to buying businesses, she sees a team or scheme acquisition as the more likely route. That conversation is already underway at the group level.

Jackson acknowledged the unconventional nature of her appointment. “Appointing a 28-year-old who joined the industry five years ago isn’t necessarily the obvious or safe choice on paper,” she said. “They could have easily decided to bring somebody in with 20 years’ management experience. But instead, they looked at what I’d achieved, my relationships within the business, my understanding of the business and they believed what I could become.”

She sees it as a model for how succession planning should work. “It’s not just identifying someone who can do the job today, but where will that person be in two, three years’ time? You can give people experience, but recognizing future talent is something that people really struggle with.”

Preston invested heavily in her development and Jensten Group took a chance. Jackson feels the weight of that. “I very much feel like I have to repay them at the moment,” she said. “I’m not there yet, but they gave me that opportunity and I’m just very grateful for that.”

Five years ago, Jackson describes herself as “quite ditzy,” more focused on appearance than anything else. She didn’t know what insurance was or what a premium meant. Now she runs a 50-year-old broker with a £11m book of business. Her approach to leadership blends the tenacity she developed climbing the ranks with a commitment to staying true to herself.

“I want to prove that you can be a serious business leader, but you don’t have to typically look like your corporate managing director,” she said. “I’m doing things slightly differently, but I just feel like I should keep my personality while doing the role and, hopefully, there’s a little bit of Essex in every boardroom.”