In the Lead

Jolee Crosby and Darlene Stevenson may not know each other, but they have much more in common than they realize. Both are women leaders in the insurance industry, and each has worked for global giants. Throughout the 30-plus years in their careers, they have successfully navigated multiple rounds of industry and organizational consolidations. Perhaps most importantly, despite the misconception that women leaders must be cutthroat to succeed, Jolee and Darlene are incredibly nurturing and supportive—two traits of theirs that I’ve had the privilege of experiencing.

I sat down separately with Jolee and Darlene to discuss their career journeys. As we talked about compensation, introspection and charting one’s path, I was surprised by the similarity in the advice they each offer to young professionals. I hope The Actuary audience finds their responses to the following Q&A as insightful as I have.

What’s your current role, and what do you love about it?

Jolee Crosby (JC): I am the CEO of Reinsurance Canada at Swiss Re. I love so many aspects of my job—the clients, the topics (Property and Casualty [P&C] and Life and Health [L&H]) and especially the team. I am fortunate that I get to work with an incredibly diverse group of individuals who are just as passionate about the value of insurance and how we need to get insurance in the hands of more people because of its role in creating a resilient world.

Darlene Stevenson (DS): More than a year ago I joined Wylie-Crump Limited, a specialty risk advisory and insurance brokerage firm that stands beside our partners to help build their companies as well as our communities. As the COO, I am actively involved in strategic and tactical initiatives alongside the executive team. I love the agility of local decision-making, the growth-minded entrepreneurial spirit and the ability to see the direct impact of my contributions. A key priority is fostering the corporate culture through personal conversations, group initiatives, formalized mentorship and promoting our Learning and Development program. I have appreciated the opportunity to stretch into responsibilities outside my comfort zone. I am also really enjoying the social nature of our team as they are a fun group that truly cares for each other and together celebrates our success.

What advice would you give to someone starting out their career in insurance?

DS: Be humble, learn all the ropes, be curious and ask a lot of questions, take notes, develop relationships at all levels, not just with your manager (you never know who will actually be a good mentor or advocate), be open to all kinds of mentors throughout your career, take a personal interest in the people you work with and go into the office. When offered a promotion or salary increase, ask yourself “Am I worth that money yet?” There is an expectation that if you are being paid a big salary, you will provide the value (ROI) and early in your career, that may be unrealistic. Learn how the business world works and be vocal at the right times about what you want, but also be prepared to demonstrate what you have done to earn it. Most recently, I’ve discovered how impactful the culture of a company and its leaders can be when they truly live their values that align with our own so research this by talking to employees that work for an organization to get their perspective.

JC: For those who are just starting out in insurance, my advice is to be inquisitive, ask lots of questions, and explore. Explore the world of insurance so that you have a strong technical understanding of how insurance works across the value chain. I would also say don’t let fear dictate your life choices. I see so many people self-censor, thinking they aren’t qualified to do something or that they will fail if they try. Even if they “fail” (and I hate that word), the learning opportunity will be incredible. More times than not, I have seen people succeed. When I switched from P&C to L&H and moved to Asia, I was told I was making the biggest career mistake of my life. It was scary! If I had listened to those people, I wouldn’t be in my current role or have had the adventure of living in Singapore for two years.

Do you have any advice for individuals mid-career?

JC: I would encourage those who are in mid-career to figure out what their passion is and then chase that passion down the career path of their choice.

DS: This is a coveted talent demographic that is under-resourced but highly desirable for organizations enacting succession plans for the boomers and Gen-Xers who are departing. Focus on client service and teamwork, really honing your craft (delivering on what you promise) and developing your own successors. If your career level has progressed faster than would be expected of someone with your knowledge and experience, take time to enroll in courses, learn from those “experts” still in the industry, and seek opportunities that hone your skills. Ten years of experience is not the same as one year of experience repeated 10 times.

When it comes to compensation, how does one know their worth and how to address potential shortcomings?

DS: In my career, I found it very difficult to ask for raises, but there were key times, such as when I returned from maternity leave and took a stand to demand a four-day week, which at that time was really unheard of in our industry. Knowing what you are worth comes from research, taking the initiative to set objectives, and getting feedback from your manager, as well as mentorship and coaching. Mid-career is the stage where you need insight to break out of your comfort zone, which can be a blind spot to obtaining higher-level compensation for the value you bring.

JC: That’s a great topic, and I’m glad you raised it. It really challenges our internal beliefs that we must remain humble and just hope that people will see our worth. On top of that, when you have this fear of rejection it’s hard to advocate for yourself. To understand your worth, you need information. I’m happy to see all of the pay transparency regulations coming out because that helps provide some data from a market perspective. But you have to apply that to your personal situation to determine your next steps. Ask questions like, “Where am I on the pay scale?” “Am I above or below the benchmark?” “If I am below the benchmark, what are the things I need to do in order to get to or above the benchmark?” Again, information is power. Once you have the information the advocacy is much easier.

Was there something (an interaction, book, event, etc.) that changed the trajectory of your career?

JC: Definitely. When I moved from P&C to L&H, from Claims to Product Development, and from the U.S. to Asia, it completely changed my career trajectory. I proved to myself that I could be comfortable being uncomfortable, which is an important leadership quality. As a leader, you will never know everything (nor should you!), but you still have to find a way forward by building a team around you, asking the questions others are thinking but not verbalizing, creating a strategic vision, and then leading through the change. It was such a fulfilling journey, during which I learned a lot about myself as a leader and had a fabulous adventure with my family too!

DS: There were many aspects that led to my decision to change companies, but to identify an “aha” moment, I would say reading two books: “How Women Rise,” by Sally Helgesen and Marshall Goldsmith, and “Who Moved My Cheese,” by Spencer Johnson. Humans are built to thrive with change, but our brains are designed to focus on the past instead of seeing possibilities for the future. A positive attitude, patience and consistent energy are essential.

What drives you?

JC: Helping other people. I’m a servant leader—with a dash of catalyst. I’m always looking for opportunities to help teammates excel.

DS: I like having challenging goals and being recognized as a high performer. While I do like personal recognition, one thing that has stood out to me as very incentivizing in my new role is the focus on building a team that cares about our clients and each other. The freedom of local decision-making has allowed me to take action and see the tangible results in a short amount of time. I also love variety, so being in this role, which is both strategic and tactical, has been really energizing.

How do you strike the balance between an internal scorecard and external validation?

DS: That is an excellent question! I have been told that I have a high EQ and self-awareness, which help me understand how others perceive my performance against the internal bar I have set for myself. I have learned through observation and feedback that the perfection trap can lead to rigidity and fear of failure, which leads to missing out both personally and professionally, so I have been working on that. I realized in recent years that helping other high-performers get over this hurdle is a motivation that drives me.

JC: I’ve spoken with many of my mentees about the need for external validation and what it means when you don’t always receive it. When you ascend as a leader and your responsibility grows you will receive less and less praise and recognition for a job well done. So, everyone must determine how to evaluate themselves as a leader—it’s your own North Star. For me, it’s all about my team: how can I give them opportunities to shine and help them grow? That doesn’t mean I don’t also focus on delivering strong financials and meaningful client relationships—but when I evaluate my own personal success it is about my team because they will be my legacy.

You are both mothers. Please talk about your work-life integration and how it has evolved as your children have grown.

DS: I am very lucky to have a partner who is extremely encouraging and who pushes me to take on challenges when fear is holding me back. He proactively undertook household chores such as cooking, laundry and childcare so that I had the bandwidth to focus on my career. I am very thankful for his hands-on and emotional support and with that extra push when needed. It was also very rewarding for my teenage son to observe how hard I worked when we were at home during COVID-19 as he now has a realistic concept of how much effort goes into being successful at work.

JC: Like Darlene, my partner has also been very supportive. Interestingly, when our children were young, I was a tele-working, part-time working mom, while he focused more on his career. Around 12 years ago, we swapped, with him taking more familial responsibility. That transition required lots of good communication. But while I had a supportive partner, I still love being Mom, so I didn’t want to lose too much of that. That’s where I have been fortunate to work for a company and managers where I had the flexibility to attend field trips, school activities and all those important milestones. I am grateful.

Darlene, after 30 years with a global broker, you made a change. What prompted the decision, and what impact did it have on choosing your next role?

DS: During COVID-19, my previous organization was in the process of being acquired, which took much longer than it should have. This led to extremely high turnover at all levels, particularly in senior roles. I supported and encouraged colleagues who remained loyal to the company, and they responded amazingly well. I also had to recruit new talent by articulating the vision about the opportunities they could have in a stressful, uncertain environment. This experience taught me that I am more resilient than I realized.

Working through difficult times is an important foundation for personal growth and very rewarding when coaching others through challenging situations. I had an influential manager who said, “Where there is ambiguity, there is opportunity.” This experience provided me with a very clear vision of what I wanted (and didn’t want) from the next opportunity.

Jolee, you are an attorney by training, yet you’ve embraced and thrived in a different territory with each subsequent role. What’s been the underlying driver of this?

JC: I’ve had some incredible mentors who pushed me to think bigger. It started with my grandmother, who always challenged me to explore the world and be inquisitive—and not let my relatively humble beginnings define my potential. She believed in me. Being an attorney trained me to be inquisitive, learn new things and take some risks. So, from the beginning, I had the fire, then I had the training and now I have an incredibly supportive network to help me continue in my learning journey.

What does success and fulfillment mean to you?

DS: Contributing to the growth and success of the team that I work with and having a positive impact whether that is personal or professional. I like to work hard, problem-solve, have variety and be challenged in my work. Building a vision and communicating that in different ways to help others see what they are capable of is extremely rewarding.

JC: My purpose is to help others find, explore, and reach their full potential. I spend a lot of time with my mentees understanding what their passions and aspirations are. I’ve found that when people have clarity of who they are as individuals and leaders, they are able to find purpose in their careers. That’s what has happened to me! There’s nothing more fulfilling than to see that happen. Five years from now I won’t remember what deal we won or lost, but I will remember when a mentee worked hard to achieve something they aspired to.

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