EBA’s Top Women in Benefit Advising

From managing millions of dollars in business and taking on leadership roles to being the only woman in the boardroom, these 20 women exemplify the best the benefits advisory space has to offer.

Each of Employee Benefit Adviser’s Top Women in Benefit Advising has stood out both professionally and personally, some overcoming heavy odds to build successful practices and develop skills in demand by all clients.

Charity Daniels, president of Bottom Line Benefits, recounted how she started in the industry under her father's tutelage, and shared her later struggle of running and managing her family-run agency after her father died unexpectedly in 2015.

"I learned that I would have to demand the respect I knew I deserved, even if it meant turning down prospects and clients," Daniels says.

She’s among many making strides in a largely male-dominated industry. See this year’s winners, chosen by EBA’s editors and listed in alphabetical order. Please share your thoughts and experiences with us and on Twitter using the hashtag #TopWomeninBenefitAdvising.

Casey Armstrong, president, Armstrong Fairway Insurance Agency
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What are you most proud of in your career?
My agency was honored with the 2016 small business of the year by California Assemblyman Jay Obernolte and has also been honored with the best insurance agency of the year, voted by local residents, for nine years straight. I am proud that I found the courage to step out of my father's business and start my own agency from scratch.

What is your biggest challenge as a woman in the industry?
My biggest challenge as a young woman in the insurance industry has been finding my voice and gaining the respect as a professional businesswoman. We have to be twice as smart to even get in the door, then four times smarter to earn the business. People are unconsciously biased; most don't realize.

Read more about Casey Armstrong here.
Catherine Borbone, executive vice president, Alliant Insurance Services
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What are you most proud of in your career?
Recently I had a difficult sale — one that took more than eight years to close. I just won this account in February. It was a tremendous process that took many meetings. It was a true victory. I had “captured my whale,” as my managing director called it. I also take pride in the mentoring I have done for the young talent in my office. It has been incredibly rewarding to watch them grow and develop and achieve their goals.

What has been your biggest challenge as a woman in the industry?
I am often the only woman in the boardroom as our industry is male dominated. But being the only woman does have its advantages. I can speak up directly to those C-Suite individuals in the room. I have the confidence and the proven results which allow me to share my experience with assurance. This is what I am trying to teach those new to the industry who I am mentoring — speak with confidence and assurance and don't doubt yourself.
Megan Cook, founder and CEO, Company Adept Benefits
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What are you most proud of in your career?
I'm most proud of the recent work I've been doing with employers to reduce their healthcare costs by 30 to 50%. I’ve also been working to provide free healthcare services to employees and higher quality care.

What has been your biggest challenge as a woman in the industry?
The biggest challenge has been dealing with the perception of being a woman-owned employee benefits consulting firm in a good old boy's club industry. Also building the confidence to not second-guess myself. I know I'm capable and continue to prove it to myself, but fear and insecurity sometimes slip in. I constantly have to work on my self-talk.
Charity Daniels, president, Bottom Line Benefits
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What are you most proud of in your career?
I started my career under my father’s wing. He was the founder of our agency and passed away unexpectedly in 2015. After his death, I was approached by more than 20 agencies and colleagues telling me to sell the business. They said it would be impossible to stay afloat now that he was gone and a 28-year-old woman was running things. Thinking about what I learned from my dad, I passed on all offers and moved ahead reassuring clients, hiring new employees and coming up with my own new strategies. I am going into my fifth year running Bottom Line Benefits without my dad. In the face of adversity and strong odds against me, I was able to retain clients, grow our revenue, grow our team, provide a family-first environment for my employees and carry on the place my dad started.

What has been your biggest challenge as a woman in the industry?
After my father died, I received a call from one of our clients. The CEO wanted me to meet with his team in order to “plead my case” as to why I should remain their broker. I sat through a three-hour question-and-answer session. When it was over, the owner asked if I needed anything before leaving, I replied, "Yes, a decision.” There will always be someone who questions my knowledge and my expertise simply because I am young and a woman. I learned that I would have to demand the respect I knew I deserved, even if it meant turning down prospects and clients. I reminded the CEO that my time deserved to be respected, and I would need an answer by the following Friday, otherwise I would no longer be negotiating their renewal. We are going on 15 years as their broker.
Allison De Paoli, founder, De Paoli Professional Services
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What are you most proud of in your career?
Moving the medical portion of our business to a fee-and-pay-for-performance structure, rather than a commission basis. We have a few older groups that we are paid a commission on, but all the new business is fee for service. It forces us to prove our value every day.

What has been your biggest challenge as a woman in the industry?
I do think the rules in any industry are a bit different for women than they are for men. But, if you are smart, creative and passionate about what you do and believe, those rules will work themselves out. I believe that the employee benefits field allows a better-than-average chance for that to happen. When I was very young, I had a client who insisted on calling me pussycat. My wonderful boss taught me how to solve that problem, and not freak out. I suspect that no one would call me pussycat today.
Aimee DiBartolomeo-Cody, president and owner, Premier Benefit Plans
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What are you most proud of in your career?
Running and growing my family-owned business, which was founded by my father in 1995; I joined in 1998. Today, we have 20 employees and more than 500 clients. I am also proud to mentor other women in the insurance and benefits industry, who are just starting out in their careers. Being able to help women break into the industry and advise those who have already started their career has been an honor.

What has been your biggest challenge as a woman in the industry?
A big hurdle I faced early in my career was gaining access to the male leadership and decision makers I needed in order to add new clients and grow my business. As I grew professionally, this became less of a challenge. Being true to myself was incredibly important to overcoming these obstacles. I faced the same challenges that my male colleagues encountered within the industry.
Ashley Ferguson, senior vice president of sales, Hodges-Mace
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What are you most proud of in your career?
The best part about being in sales leadership is seeing associates achieve their goals. That could be selling their first deal, selling their largest deal, breaking through with a referral channel, getting promoted, exceeding their yearly target or exceeding financial goals that impact their personal lives and families. My proudest moments have been witnessing these achievements for associates that have worked for me. It never gets old to see people work hard towards a goal and achieve it.

What has been your biggest challenge as a woman in the industry?
The biggest challenge is that there are not enough women in high level executive roles. When you get there it can be a lonely place. The women who are up and coming in the industry have very few people to look to as role models so it can produce doubt that it's even possible to get there. We need to do a better job across all industries making woman executives visible and telling their stories so the future generation knows that it is possible. As female executives, we have a role to ensure we mentor new associates. I was fortunate to have great female mentors that took an interest in me and provided me feedback and guidance. I have a role in paying it forward just as others did for me.
Amy Fossum, senior vice president, Alliant Employee Benefits
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What are you most proud of in your career?
My success as an employee benefits broker. I have helped so many employers over my 19-year career. I love what I do and that alone is something to be proud of for sure. I've built such special relationships that will last me a lifetime.

What has been your biggest challenge as a woman in the industry?
When I started in the insurance business, it was dominated by men. I am competitive by nature and was sure I could be successful. I got married and had my first child within a year of becoming a broker. I recall attending finalist presentations nine months pregnant and reassuring potential and current customers I would always be there for them. Balance is sometimes tough in this role, but with the support of my husband and family, I have overcome the challenges of being a working mom.
Jill Goldstone, area vice president, innovation, Gallagher
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What are you most proud of in your career?
I have had the opportunity to develop strategies and resources focused on
the impact opioids have on our clients and their plan members. By proactively addressing substance abuse and prevention in the workplace and the stigma surrounding it, we have the opportunity to save lives. Leading this effort has truly been a passion of mine.

How has the benefits advisory space evolved since your career started?
I started in the early days of HMOs, paper enrollments and manual underwriting calculations. When you needed to consult with an underwriter or connect with a client, phone or in-person were your only options. Technology has certainly enabled the most dramatic changes, from the way we communicate, enroll in benefits, research options and access healthcare. More unbundled solutions are now available for employers and there is a greater need for consultants to be aware of the rapidly changing landscape, so that we can properly advise clients.
Tammera Hollerich, executive advisor, Insurance & Benefits Team
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What are you most proud of in your career?
I am proud that before the ACA was implemented, I took the agency to a fee-based model, forcing transparency in a field that was totally commission-based. This really gave us a point of difference and secured our integrity with our clients.

What has been your biggest challenge as a woman in the industry?
The early years, while I was still in my 20s, were the most difficult. Due to the fact that this industry is primarily male-dominated, a young female was stereotyped as a secretary. When I would show up for a bid opening, I was typically asked who I worked for instead of assuming I was there to help them as an adviser. One time I was even called sweetheart — talk about frustrating.
Janette L'Heureux, managing advisor, Baldwin Krystyn Sherman Partners
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What are you most proud of in your career?
The ability to always do what is right for the client. To hold myself to a high standard and demonstrate professionalism, integrity, grit and a passion for what I do.

Why would you recommend this career to another woman?
Being an adviser is challenging and has its highs and lows. But when you partner with a client and successfully manage the second or third largest line item in their budget, it is very rewarding. When they refer you to another potential client, you know you have made an impact. I encourage all women to consider a career in the insurance business as it is not only rewarding, but a business where you can build relationships that last a lifetime.
Tonya Manning, U.S. wealth practice leader and chief actuary, Buck
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What are you most proud of in your career?
Attaining my fellowship with the Society of Actuaries required dedication and hard work. It opened many doors in my career. Without it, I would not have been able to serve as chief actuary for two large consulting firms, lead Buck's Wealth practice or hold various leadership roles as a volunteer for the actuarial profession. I am also proud of my prior service as president of the Society of Actuaries, the largest association of actuaries and to be president-elect of the International Actuarial Association, representing actuaries from every part of the world. Only a few women have served in each of these positions, and I feel fortunate to provide women with further confirmation that these roles are open to anyone with the skills and desire to pursue them.

What has been your biggest challenge as a woman in the industry?
I have spent much of my career as the only woman in the room. It has taken me some time to develop a leadership style that works for me in this environment. Unfortunately, I have not had female mentors during my career, so I was left to observe men and their approach to managing and leading. For the most part, these styles were not for me. I had to figure out how to best leverage what I brought to the table as a female leader. It was with great relief that I finally settled on an approach that was both effective and true to me.
Rhonda Marcucci, practice leader, HR & Benefits Technology, Gallagher
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What are you most proud of in your career?
My involvement in start-up work, particularly building new business units within an existing company and nurturing them into strong revenue centers. This led to my decision to build my own company, which I formed in 2005 and then sold to Gallagher in 2017. I continue to oversee the same work, together with my former business partner. I am most proud of my work as CFO of Viaticus, a viatical settlement company formed in the mid-1990s. A viatical settlement is when a terminally ill person sells their policy to pay for life-extending medical treatments or to fulfill a personal wish — it can make a huge difference in their lives. I was responsible for designing, implementing and supporting the overall operations of a new company that became the market leader in an emerging industry in less than 24 months.

What has been your biggest challenge as a woman in the industry?
I never bought into the idea of challenges related to gender. Both my parents worked in a small business and there was no conversation around men versus women. I’m the oldest of four children, and there were high expectations placed equally on all of us. I believe that we each bring our own mindset to our career and there's a risk of being a self-fulfilling prophecy. Because I never thought about gender as a disadvantage, I innately rejected the idea that being a woman presented any unique challenge. Because I don't view the work environment that way, I believe there is less opportunity for others to impose challenges or limitations on me because I am a woman.
Brandy Oglesby, senior vice president of benefits consulting at Alliant Employee Benefits
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What are you most proud of in your career?
The impact I have on the employees I work with. Typically, their first interaction with me is full of confusion, anger or fear. This can be due to a change in their benefits, an acquisition or even a newly diagnosed condition of their own or for a loved one. They are looking for someone to help ease their concerns, guide them through their options, remove the unknown and advocate on their behalf. The relief and gratitude they express at the end of our interaction is very rewarding. Knowing that I have removed this stress factor from their lives and impacted them in a positive way is a great feeling.

What has been your biggest challenge as a woman in the industry?
The consulting and brokerage space has always been a male-dominated industry. Finding my voice was a hurdle. Getting carrier partners, executives, C-suite and male peers to view me as a fellow expert and value my consulting, opinions and contributions, instead of just focusing on my client service capabilities, was challenging. I strive to continue to break that cycle and mentor my female peers the best I can and empower them to be strong consultants.
Jennifer Parks, founder and president, HealthPointe Insurance Services
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What are you most proud of in your career?
Leaving the giant agency I once worked for and starting my own in 2008. It was a tough road at first due to my non-compete and the recession, but I knew that I wanted to serve my clients and their employees with a more customized and nimble approach. It has turned out to be the best decision I've ever made.

What has been your biggest challenge as a woman in the industry?
When I first started in the insurance business in the late ‘90s, most of the women in the industry were in service roles and there were very few women producers. I began my career working in my dad's property and casualty agency and his partners were reluctant to see me as anything more than a customer service rep. I was the only female producer in an agency of about 10 total producers. I proved myself early on by winning three very large benefits accounts and my dad would often comment, "Jennifer is the only producer that we've ever hired that didn't cost us anything."
Pattysue Rauh, executive vice president, Brown & Brown
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What are you most proud of in your career?
I was asked to become the national benefits leader for Brown & Brown, a position that had not existed within our organization. Brown & Brown needed someone to take a leadership role to develop and execute on national initiatives to not only help our teammates, but our clients. This was the beginning of what has become a focus within Brown & Brown, and now an entire leadership team works together transforming our company and the industry.

What is your biggest challenge as a woman in the industry?
My biggest challenge has been balancing work and family. Having two children while maintaining a demanding career has, at times, created a situation whereby I was not always able to be at my children's activities. As they have grown up and turned into young adults, my hope is that I have instilled in them that sometimes sacrifices need to be made so that you can provide for your family.
Polly Thomas, president, Employee Benefits, CBIZ
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What are you most proud of in your career?
I am proud that I took the risk of leaving a career in another industry 10 years ago to join this profession. The work has been challenging but far more rewarding than I would have anticipated. I am also proud of the innovations and successes my clients have achieved in evolving their total rewards programs. From winning national and international workplace well-being awards to managing plans, our clients have achieved meaningful results. I am also proud of the team of employee benefits professionals that I have developed.

What has been your biggest challenge as a woman in the industry?
The biggest challenge has been getting a voice and a seat at the table in a traditionally male-dominated industry. Fortunately, my firm has the CBIZ Women's Advantage program, which helps women in our industry and the community grow and develop. Participating in this program has given me the strength, skills and support to overcome this challenge.
Stephanie Shields, senior vice president, broker sales, Aflac
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What are you most proud of in your career?
I am most proud of the teams I have built and developed that deliver strong financial results to the business. I am an advocate for setting people up for success by leveraging their strengths. I have always aligned my team's work assignments based on individual talents versus job titles. Creating a high performing culture based on collaboration, taking risks and having honest conversations has been core to how I have operated. I am inspired by my team daily and the business results speak for themselves.

Why did you choose this career?
I originally chose this career because I loved the idea of consulting with clients to solve problems or find creative solutions for delivering employee benefits at the workplace. I was drawn to the rich talent in this industry and the fact that much of our business is built on long-term relationships. There has never been a typical day since I started 20 years ago. I have had the opportunity to work in so many parts of the business, on both the carrier and consulting side, in distribution and in corporate execution roles. I am always been energized about how much opportunity this industry presents for personal growth and development.
Michelle Sullivan, senior vice president, USI Insurance Services
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What are you most proud of in your career?
I am most proud of building a substantial client base with more than $5 million annually in consulting fees. I am also proud of building a dynamic account management team with impressive credentials, meaningful experience and diverse backgrounds.

What has been your biggest challenge as a woman in the industry?
Early on, I was one of the only female benefit consultants in Atlanta, and it was difficult to be taken seriously. Once people understood I had a master’s degree in actuarial science and agreed to meet with me, their opinions changed. I believe being a female today is an advantage. My clients know I will always answer my phone.
Tamara Volkert, senior vice president and director of employee benefits, Hunt Insurance Group
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What are you most proud of in your career?
I am most proud of being an out of the box thinker and having the ability with my current employer to design creative insurance solutions. I am passionate about educating our clients on making the most of their benefits. I was the lead on building an innovative medical consortium for one of our programs and that has been one of the biggest accomplishments of my career.

What has been your biggest challenge as a woman in the industry?
The stigma of insurance sales being a man’s domain. While I have seen many positive changes in that perception over the years, there are times that it's still there. Women are rising up in the insurance world and it's been really exciting to be a part of that.