Women in Insurance: Yosha DeLong, Global Head of Cyber Underwriting, Mosaic Insurance

Women in Insurance - May 19 2021

In this interview series, we profile women who are shaping the future of insurance. This week, we connect with Yosha DeLong, Senior Vice President, Global Head of Cyber Underwriting at Mosaic Insurance. Based in Chicago, Yosha is responsible for the development and oversight of Mosaic’s cybersecurity product globally. She has over 24 years’ experience in managing liability, professional and cyber lines. Yosha shares her career journey in insurance and discusses what it’s been like to launch a new cyber insurance product from scratch in the midst of a global pandemic.

Yosha, tell us about your path to insurance. What attracted you to the profession?

I started working at an MGA in Seattle while I was going to university. I was a math major and thought I would follow the actuarial track, but I really liked dealing with people on transactional business and the negotiation and contract wording side of insurance. Like most people, I thought I would just do insurance until I figured out what I wanted to do with my career – and 24-plus years later, I’m still here and loving it.

Mosaic officially launched as a specialty insurer in February and, a few short months later, in April, began offering cyber coverage to middle-market businesses. It’s not every day that a new insurer comes on the scene. Can you tell us about the company and what it’s been like building an underwriting team and launching a new cyber insurance product during the pandemic?

Its been a busy and exciting 2021! It’s not every day that you get the opportunity to build a cyber product offering and underwriting team from scratch. We have the right leadership and partners in place to build a successful, focused insurance company—one that truly values a discerning approach to the underwriting of complex products. We have been able to attract highly-talented people to the team and are building our cyber portfolio in a hardening marketing. The feedback we are getting from the broker community is very positive and supportive and I know there is a place for thoughtful underwriting in cyber right now. My only challenge is that I don’t get to spend face-to-face time with my brokers and clients at this time. I think all of us are looking forward to seeing each other in person again in the near future.

There’s no question that cyber insurance is a hot topic today. As we know, one of the world’s largest commercial insurance carriers was recently impacted by a sophisticated ransomware attack. With the rise in ransomware and cyber-attacks, are businesses adequately insured and well-informed about the risks?

The short answer is no. Businesses are not adequately insured or well-informed about their cyber risks. We are seeing an increase in small and mid-sized businesses buying insurance, but there is still not enough of a take-up rate in that segment. There is a lot of room for market growth and for us in the insurance community to add value through education. We are seeing recent government actions starting to take place that should also increase awareness about the threat of cyber attacks, but we need to work together across the insurance industry, government, regulatory and private sector to continue to combat the bad guys, raise awareness of minimum security standards, and look at insurance as a catastrophic backstop to this issue.

Traditional insurance carriers often face challenges with legacy systems and tech debt. Can you speak to the advantages of being able to build a company and an underwriting practice on a modern, up-to-date infrastructure?

This is one of the most exciting parts of what we are building. The insurance industry has always struggled with data and systems. Most insurance technology is designed around P&C lines of business. Mosaic is in the unique position of being able to custom-build a legacy-free insurtech platform geared to our specialty lines of insurance. It will provide end-to-end efficiencies and allow us to pull real-time data that is so important to cyber, including claims data and accumulation. Additionally, using machine learning and AI, we’ll be able to streamline the process part of underwriting, freeing up our team to focus on account analysis rather than getting bogged down in paperwork. In the long run, we will have an advantage in the marketplace to track threats and trends. I believe this cutting-edge access to data and insights into our portfolio will also allow Mosaic to attract the best third-party capacity and reinsurance partners.

What types of data are required to effectively evaluate cyber risk and make underwriting decisions?

At Mosaic, we are focusing underwriting efforts on risk analysis. We follow the NIST framework as a guide. In addition to looking at cybersecurity measures that are important to prevent and minimize events, we also try to get a feel for a company’s overall cybersecurity culture and where they are on their cybersecurity journey. The best way to do this is always an in-person (well, now virtual, but live) meeting. The questionnaire process commonly used is a bit antiquated, and our industry is now finding that simple yes/no answers aren’t always the best way to really see what a company’s cybersecurity posture is. We need to get into the “gray” areas and truly understand each, individual risk, along with a company’s overall culture of security and privacy.

According to a 2017 study, just 12 percent of insurance companies’ top corporate officers are women. Why do you think there are so few women in senior leadership roles in the insurance industry?

I believe this problem is a culmination of a few factors. We haven’t traditionally recruited women into insurance or shown this to be an attractive and supportive industry for women. I do believe that is changing, and more women are looking at insurance as a welcoming career. The second factor has really been that women seven to 10 years into the industry have often had to take a step back, just as their careers were accelerating, if they chose to have families. Women continue to carry the majority of the burden of taking care of the home and family. This is very taxing when you are also trying to get ahead in your career. I would like to see more companies recognize this and support women through this time and if women choose to take a step back to focus on their families, we, as an industry, should be welcoming when they refocus on their careers. It hasn’t always been easy being a woman in this industry; I know most of my peers feel as if we have to work twice as hard for less recognition. Thankfully, there has been a change in the good-old-boy culture that insurance thrived in for many years.

What advice would you give the next generation of women considering a career in insurance?

Give insurance a shot – it can be a very rewarding career. But also, I think, as women, we really need to support and encourage each other through all phases of our careers, not only in insurance, but across all industries. It’s my job to help mentor and advocate for women in general. And we also need men as allies in our career journey. I’ve been lucky to have incredible women as role models and incredible men as mentors and advocates. It’s really made a difference in my career and I hope I can pass it on and do the same for others.


delong, yoshaYosha DeLong, SVP, Global Head of Cyber Underwriting for Mosaic Insurance, has more than 24 years’ experience in managing liability, professional and cyber lines. Based in Chicago, she is responsible for development and oversight of Mosaic’s cybersecurity product globally. Previously, she was technical director of cyber and professional lines at Zurich North America, where she coordinated cyberrisk coverage across all lines of business and oversaw professional liability lines. She held prior roles at Gemini Risk, Ironshore Insurance, and Axis Capital.

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