The diverse path to a robust cyber insurance market

The complex problem of cyber risk requires ‘cognitive diversity’ to create a truly ‘potent’ solution, says Rebecca Bole of CyberCube. Intelligent Insurer meets a leader who describes her 25-year career as non-typical, with a key role in shaping the future market for cyber insurance.

Wanderlust might not be the first thing that comes to mind when considering a career in insurance. But for Rebecca Bole, head of industry engagement at CyberCube, it was a major factor in her career choice. And this broad outlook on life and business has served her well over her 25-year career.

Bole explains that as a language graduate she had a strong wanderlust and was initially drawn to the global nature of insurance.

“I had lived and worked a bit abroad and I was excited at the prospect of working across different regions and cultures—the insurance industry offered that.”

This interest became Bole’s first role in insurance, on the Lloyd’s graduate training scheme in the mid-1990s.

“Lloyd’s gave me a great grounding in the entire sector, I was employed by a managing agent, but I was spending time learning about the corporation, brokers and things that were outside my day job within the syndicate on which I was a trainee underwriter.”

Bole continued to underwrite at Lloyd’s for 10 years as a financial institutions specialist. For seven of those 10 years, she says she was “very lucky” to work for ACE, now Chubb, within its syndicate, and particularly to work with Andrew Kendrick “an industry legend, now retired”. 

“Andrew had a great passion for the industry and was very progressive in nurturing talent from all walks of life. He wasn’t swayed by the old school tie, which was very much a default for hiring at the time. 

“Working for Andrew gave me some early progress in the industry,” she recalls.

“ACE, unusually at the time, had a female-led underwriting team. We were unique at the time, we were a lead syndicate for financial institutions. It wasn’t easy and it wasn’t always particularly accepted in the Lloyd’s environment. But it was empowering to be part of that team.”

Change of direction

Bole says that although Lloyd’s was an amazing place to spend her early career, she decided that the linear career path of an underwriter “didn’t really light my fire”.

She followed her instincts and took “a 90-degree turn from being an insurance practitioner to being an insurance observer”, with a role in the media.

“What interested me is that insurance is relevant across all aspects of society. I was in the weeds thinking about financial institutions and the risks they face, and how I could create products for their risk transfer. It was very focused, and I wanted to take a step back and observe the sector from a different angle, and enable some of that broader growth.”

Working in the media enabled her to write, manage and launch publications, which touched on a range of insurance sector areas.

“These were established sectors of insurance and some of the emerging ones. I was building communities of professionals, bringing them together to solve complex problems.”

“To seek talent from different backgrounds, perspectives, and expertise is super-important across the industry.”

Rebecca Bole, CyberCube

Cyber is fundamental

“My role immediately prior to CyberCube was running the media business of a data company. One of the main areas the company operated in was data around cyber risk and cyber insurance losses. 

“I’d already started to get involved with the cyber insurance marketplace in that role and it opened my eyes to the fact that cyber is a very important societal theme.”

With the ever-advancing digital revolution, Bole says that cyber and digital risk are “going to be fundamental themes for society in the coming years and that had already sparked an interest for me”.

She joined CyberCube in September 2018 as a member of the leadership team responsible for setting and executing strategy for stakeholder engagement on cyber risk and insurance. She is in charge of the marketing and outreach strategy for the company, engaging with key stakeholders in the cybersecurity, risk, governance and insurance communities.

CyberCube’s clients include Aon, Guy Carpenter, Lockton, Chubb, CNA, Munich Re, Hiscox and Woodruff Sawyer.

Her role at CyberCube tackles the complex manmade, yet intangible, problem of cyber risk as new technology is being adopted across society at such a speed that risk management is finding it hard to keep up.

“The gap between the technologies being adopted in society and managing that risk is opening, and those financial losses can be huge. That’s a cue for the insurance industry to come in and help bridge the gap. It’s uniquely positioned to help unlock the potential for the digital revolution,” Bole says.

She recognises that there are obstacles for the insurance industry in developing a robust cyber insurance sector and says CyberCube’s “core focus” is on helping the insurance industry solve some of those problems.

It’s well placed to do this as the firm is coming at the problem from a pedigree of cyber insurance and approaching it as a software and service technology company, she says, referring to the company’s history. The firm launched out of Symantec, a Silicon Valley cybersecurity company, to become a standalone company in 2018.

The calibre of the people at the company was another draw for Bole, who says there’s a “genuine cognitive diversity” within the team.

“This talent has come from all over, and that is what’s brilliant,” she says.

“Diversity and inclusion (D&I) are key to creating a potent cocktail of talent to tackle the complex demands of cyber risk,” she adds.

Bole’s passion for cyber risk’s complex problems, the talent she works with, and the company are clear—but another element attracted her to the role.

“CyberCube is an early stage technology company, and I’m an insurance girl. The opportunity to be part of the leadership team in a fast-growing tech company that comes out of the cybersecurity sector but is applying itself to the insurance industry is a very interesting professional development opportunity for me,” she says.

“We are here for the long term to develop a profitable, robust, cyber insurance market for the entire industry, not just to sell products into it.”

The value of cognitive diversity 

As a woman working across two predominantly male-led industries (insurance and technology), Bole is adamant about the value of cognitive diversity.

“We need to have that cognitive diversity to solve complex problems. To seek talent from different backgrounds, perspectives, and expertise is super-important across the industry. Having female leaders is a very important part of that. 

“Women bring a different approach to leadership and problem-solving. They often have different life experiences before becoming leaders that they can bring to bear on shaping an industry or strategic thought,” she says.

For Bole, becoming a leader herself was characterised by incremental steps forward.

“You almost don’t realise that that is happening as you go through your career. You are building up experiences, with different challenges and different ways to overcome them.

“You have different role models and mentors to turn to for advice on how you develop your career or how you deal with certain situations.”

There are key things that build a leadership trajectory, she says.

“Obviously, you have to know what you are doing, you can’t lead just with soft skills. You need to build up technical skills and be good at what you do. If you don’t have a passion to be good at what you’re doing right now, then find something else where you will have a passion to be good.” 

Technical ability alone is not enough however, she says, emphasising the importance of the soft skills that can be layered on top of that. 

“As a woman, I found that embracing differences was very important. A long time ago I decided to bring the authentic Rebecca Bole to work, not an image of what I thought others wanted me to be.

“For a while I did fall into the thinking of ‘I’m a woman in a man’s world, therefore I have to be a man in a skirt’. But that wasn’t me, I wasn’t bringing myself to work, so I wasn’t doing the best I could do in a role.”

Bole recognises that her progression as a woman was “probably smooth compared to some of my peers” but, she says, it wasn’t easy all the way through. 

The industry is making great improvements in the area of D&I and there is a much more concerted effort today to attract diverse talent, which is bearing fruit.

“One area where I would like to see more work done across the industry as a whole is in supporting and nurturing that talent.

“Without such ongoing support, the success of getting the talent through the door will be relatively short-lived,” she says.

Bole is quick to mention the many great initiatives currently boosting D&I across the sector, such as the Dive In Festival and the work of the Insurance Supper Club, the female networking group. She notes D&I efforts within corporations themselves, such as Guy Carpenter’s Embrace, and at CyberCube, Bole is leading a programme of initiatives around gender diversity.

“We are putting in place a programme of different initiatives that are internal to CyberCube but we hope they will also have an impact through insurance and the tech industry.”

The initiatives around gender diversity fall into three areas: attracting the best talent; supporting the talent within CyberCube; and building paths for advancement.

“A strong foundation of engagement with the insurance and tech industries is key to building a robust sustainable cyber insurance market.”

Priorities, longevity, and legacy

As a member of the leadership team, Bole says the business’ priority is to continue to build on the strong foundation established when the company launched in 2018.

“We’ve had great traction in the industry and have been building our customer base with some great clients who are wonderful partners for us. 

“We’re launching new products, new ways to access our data and analytics for the industry, and building all that feedback in, and we’re hiring at a pace.

“Continuing on all of those fronts to keep building is a definite priority. We are here for the long term to develop a profitable, robust, cyber insurance market for the entire industry, not just to sell products into it.

“Embedding ourselves within the cyber insurance industry, stress-testing our products with the industry to make sure the solutions we’re providing are relevant and useful to them is a priority.”

Bole says that a strong foundation of engagement with the insurance and tech industries is key to building a robust sustainable cyber insurance market, and crucial for ensuring relevant products to help society to unlock the potential of all this transformational technology, but she adds “it takes an army”.

“It is not just cyber insurance practitioners who are going to do that, or the cybersecurity industry developing risk mitigation tools, or only the government or regulators,” she explains.

“It is going to be a community of stakeholders, and as head of industry engagement that’s my main priority: to build relationships with all those key stakeholders and build the broader community that together can help solve some of these complex problems, and help build the governance framework.”

She says she will spend more time with stakeholder groups to work on understanding how to think about cyber risk, what some of the signals are, and the scenarios that could cause catastrophic loss. 

CyberCube has “genuine growth opportunities” within each of its products, she says, adding that in terms of geography, the cyber insurance industry remains focused around insurers based in North America or Europe, meaning they will remain key regions.

“Asia-Pacific is also starting to develop a cyber insurance industry and that will be an area for us to expand our reach,” Bole says.

With so much opportunity for growth and grand plans to help shape and build the cyber insurance market, it’s refreshing that Bole says that one of her proudest achievements is that she is “still having fun” 25 years into her career.

“I have a great enthusiasm for this industry and working in the insurance sector from whatever angle it is that I take.

“That’s based on the decision I made a long time ago to be the authentic Rebecca Bole and to follow my own track through my insurance career.

“It has borne fruit for me in my own professional development, but I see it now bearing fruit in my role as a leader and helping the next generation of insurance professionals to find their way and develop,” she concludes.

Rebecca Bole is head of industry engagement at CyberCube. She can be contacted at:

Image: Shutterstock / Archreactor, enzozo, Sergey Nivens

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