"A Shoulder to Stand On:" InsHER Podcast Episode with Shanna Sweeney
In the latest episode of the InsHER podcast—a platform hosted by Megan Bell dedicated to elevating and celebrating female leaders across the insurance industry—Shanna Sweeney, Senior Vice President of Excess Casualty at Upland, sat down to share her career journey, industry perspective, and leadership philosophy. Shanna oversees a nationwide underwriting team specializing in complex casualty and construction risks, driving strategic growth and underwriting excellence.
Beyond her executive responsibilities, she is a seasoned educator who has taught CE-accredited courses for WSIA and the Surplus Lines Association of California for nearly a decade, as well as the President and Co-founder of Women of Wholesale (WOW), an organization committed to advancing and mentoring the next generation of excess and surplus lines professionals.
What inspired you to invest your time in creating Women of Wholesale and your career at the same time?
I never viewed these as two separate things. My career gave me so many opportunities, mentors, success, and confidence. So, Women of Wholesale just kind of became my way of giving some of that back, states Shanna.
Early in my career, I realized that success is wonderful and mostly inevitable, but it's even more meaningful when you can bring other people with you. I wanted to create a place where women could build relationships before they actually needed them. A place where they could ask questions without feeling judged, and where they realized they weren't navigating all of this alone. That there was a community around them, and maybe not so ironically, investing in others has made me a better underwriter and a better leader. Teaching forces you to learn, and mentoring keeps you humble. Building a community reminds you why this industry is worth staying in. Success is what you achieve, but significance and impact are what you leave behind.
What lessons did you learn from what women actually need from professional organizations like Womenof Wholesale?
I honestly thought that people wanted more education. I thought I was going to do classes on the CGL policy and the history of reinsurance, but what I learned in the process of all that is what they wanted was connection. Women don't necessarily need another networking event where they exchange business cards and become friends on LinkedIn. They need spaces where they can be authentic, ask for advice, and admit when they don't know something. I think really importantly, to celebrate each other's wins and create an environment where you can build trust over time. Obviously, the educational content still very much matters, but relationships are what keeps people coming back to the events. Community wasn't necessarily the initial focus, but it has become the product.
What qualities are you looking for in the next generation of leaders to carry the mission of Women of Wholesale forward?
I look for curiosity and people that ask good questions. It's one thing to be someone that's coachable and takes direction, but I really like the folks that ask and do first. I look for people that celebrate people's success without making it about themselves. It's easy to say, “Oh, congratulations on that bind order! I'm so glad I connected you with that broker.” You know you missed the mark right there.
Of course, I like to find those that demonstrate integrity when no one's watching. But I think most importantly for me, I look for people who are willing to build something that they're going to someday hand down to someone else. I really like eager attitudes. I once had a boss tell me that my eager attitude made me seem naive, and that I should tone down my excitement. I knew then it was my time to build my own brand and style of leadership. Through that journey, I've realized that leadership isn't about being indispensable; it's about making yourself replaceable because you develop people alongside you so well.
Why do you think the relationships through your career in insurance have been so impactful for you?
The insurance industry is ultimately a relationship business. The friendships were just kind of a natural happen stance because you're celebrating wins, surviving market cycles, and solving what can seem like impossible problems together. Overtime, these work conversations become life conversations. The trust in the industry typically comes professionally first, and then you eventually get to that personal level.
For me, there's a couple of women I work with: Liz Goldie and Paige Kramer. I remember when I first met them—they were broker assistants, and they were hawking $10,000 policies, and we joked that, “One day, we're going to do big things together.” Sure enough, a decade plus later, we are.
When I think about the relationships and the friendships in all of this... If I could have told my younger self that this was the part of the industry that I would love the most, I don't know if I would have believed it. I don't know if the impact would have made its way through my thick skull. But my friendships and relationships are the things that make me so proud of this industry because there are such good people in it.
How do you think women can move beyond competition and embrace genuine support of each other?
It starts with a mindset of abundance. If you have a mindset of abundance, it changes everything. When you genuinely believe that there's enough opportunity for everyone, and that another woman's success isn't your failure or your miss—then one plus one can equal three.
There's a couple of small things that you can do right away to create a culture where people lift each other up instead of gatekeeping opportunities. I'd say it starts first and foremost with celebrating folks publicly. I've been called a flatterer before, and I don'tintend on changing that. Too many times, I am inrooms where the first thing said is a slight to another underwriter or broker.It's one thing to gripe about a deal gone wrong or a bad interaction, but it'sanother to sit around ripping on your competition. I think it goes back to theold saying, “If you don't have anything good to say, don't say anything.”
In that same vein, don't be afraid to recommendsomeone for a speaking opportunity or share a stage with someone. I am often onpanels or asked to teach organizations like WSIA and the Surplus Line Associationof California, and my first ask back is, "Can I bring a friend?” When Ithink about the women that I admire most in this industry, they're not the ones that climb the ladders; they're the ones that hold it steady, so someone elsecan climb it too.
I was talking with one of your podcast guests that you recently had on, Laura. She and I were exchanging ideas, and she said,“My goal is to never step on your head,” and I replied, “My goal is to neverstep on your toes.” It brought this broader conversation: How do we bridgegenerations better? I got to where I am because I stood on the shoulders of thewomen who did the work before me, and I want to be that next set of shouldersthat the young women who work for me can stand on.
If we want to like this industry 15, 25, 50 years from now, we must do the right thing for the next generation and theincoming folks. If we don't invest in them, that ruins our future. It's allabout that next generation and how we can make the path better.
What gives you hope for the women in our industry?
What gives me hope is the women entering this industry today. This next generation of women -- they're incredibly smart.They're really technically capable and aren't afraid to ask why or roll uptheir sleeves and do the job first.
I also love their fashion. I'm an elder millennial, and I wore Skechers and oversized cardigans. These girls know whatthey're doing, so that gives me hope. They're resourceful, and that issomething I noticed right away. I am such a big fan of this next generation.
What gives me even more hope is seeing experienced leaders, both men and women, intentionally investing in them. Ourfuture gets brighter every time someone chooses mentorship over gatekeeping. Ithink our industry is becoming more collaborative, innovative, and more willingto recognize that diverse perspectives produce better outcomes and more profit.
If you were given a seat in the C-suite, what would you do to create a more equitable playing field in the insuranceindustry?
First, I would spend less time talking about diversity and more time designing for it. What that design would look like isnot just mentorship as a vehicle, but sponsorship. Mentors give advice, butsponsors use their influence. I've been really fortunate in my career to havefolks do that for me. My co-founder of Women of Wholesale, Pam Quilici, she wasmy sponsor. She said, "You can do this. I will say your name in the roomsthat you aren't in. So now I know personally how much that can change. Thetrajectory of a career,
Next, I would also redefine what success looks like and how it's rewarded. I think leadership development should be a part ofevery executive's job, not HR's responsibility. Executives should be measurednot just by the business that they grow, but by the people that they develop.
Lastly, I’d probably have some sort of hand in recruitment. I did not come from a risk management background. There are folks on my team; some of the best producers and strongest contributors that do nothave risk management backgrounds. One of our associates was a professional Pokémontrader, and now he professionally collects and trades binders. One of our teammembers worked for the FDIC. Because of that, he's our Excel guru. He can fixand do anything. So, I'm a big fan of bringing in people from all walks of life.