March is Women’s History Month, an annual observance that recognizes and celebrates the rich history and achievements of the powerful women who have helped shape our society and advance our nation. At Hagerty, we truly believe our greatest advantage is our people, and this month, we want to honor the invaluable contributions of the excellent, innovative women who make up the Hagerty team. Today, in the spirit of celebration and professional growth, we are highlighting four women at Hagerty who are truly making a difference.
1. Tell us about yourself and how your career path led you to Hagerty.
Jessi Widhalm: At a young age, I developed a passion for politics and went on to study political science/international relations and political communication at George Mason University (GMU), just outside of Washington, DC. During my senior year of undergraduate study, I interned on Capitol Hill for Congressman McCaul (TX) and was lucky enough to become his scheduler shortly before graduating with my bachelor’s degree. I ended up serving as a member of his staff for the next seven years and ultimately became his Chief of Staff. In May 2017, I joined the presidential administration as an appointee at the Federal Emergency Management Agency (FEMA), where I first served as the Director of Congressional Affairs and, a year later, was promoted to serve as the Director of the Office of External Affairs – overseeing congressional and intergovernmental affairs as well as media relations and strategic communications for the agency. Nearing the end of the administration, I was looking for a way to marry my passion for emergency management with a desire to explore communications/marketing in the private sector. I was lucky enough to connect with the team at Hagerty and be given the opportunity to start our firm’s Marketing, Communications, and External Affairs (MCEA) team. Over the last four years, a team of two has grown into a team of five, and I am extremely proud of the way our team’s services continue evolving and expanding to meet the needs of our growing firm.
Tori Abbott: I graduated with a degree in Recreation and Parks Management with a focus on Adventure Sports and a secondary degree in Philosophy from Frostburg State University (FSU) in western Maryland. While the latter exposed me to deep thinking and copious amounts of writing, my degree in Recreation introduced me to the world of Search and Rescue and First Responder training. Throughout my time as an adventure guide, I became a certified Wilderness First Responder and acquired additional certifications for search and rescue in wilderness, cave, and underwater rescue. After graduating, I became a Community Supervisor for Baltimore County Recreation and Parks for several years before eventually relocating back to the Eastern Shore of Maryland, where I am from. I fell into proposal writing and management easily, thanks to my background filling out endless “blue book” essays for my Philosophy degree and my innate understanding of (and appreciation for) organization and compliance. A former coworker introduced me to Hagerty, which led to a conversation with Katie Freeman, and the rest is history! Little did I know that my rescue and response background would come full circle through a career change.
Meagan Flanagan: I grew up in Northern Virginia. My passions include cycling, baking, and reading. I will literally read anything I can get my hands on. Living in Northern Virginia, you tend to fall into a couple of professional categories. Your work is either in the tech or government space. I have been in the Department of Defense (DOD)/Intelligence recruiting for a good portion of my career. Ultimately, this led me to work for Booz Allen Hamilton with Walter Flores, Hagerty’s Head of Talent Acquisition (TA). Walter thought I would be a good match for Hagerty Consulting and began his effort to bring me on staff. When the pandemic hit, I wanted to find a way to contribute to the problems the world was facing. I called Walter, and he had a position. This was four years ago and became one of the best professional decisions I have ever made!
Joely Bertram: Originally from the Chicagoland Area, I went for my Bachelor of Arts (BA) at Virginia Commonwealth University (VCU) to study Homeland Security and Emergency Preparedness. A leadership conference I attended in high school about intelligence and national security sparked my interest in the field and adjacent areas. While in school, I was very set on the idea of going more into the Homeland Security side of things. However, after a couple of post-graduation internships in Virginia with local/county offices of emergency management, I realized how much I enjoyed working on severe weather preparation, designing exercises for first responders, and working directly in a community. I entered the workforce with Hagerty back in September 2020. They were certainly unprecedented times, but I would not have wanted to start my career any other way. Almost three and a half years later, I still love the Preparedness Division and all the experiences I have had!
2. Please share with us a female leader who has inspired you throughout your life and career.
Jessi Widhalm: My mom is my biggest personal and professional inspiration. She was a career civil servant and, upon retirement, earned the highest civilian honors for her work in financial management with the United States (US) Navy. Growing up, I did not understand her career or what life was like for her as a single parent, but regardless of the often-difficult circumstances she was facing, she always showed fortitude, teaching me and my younger sister that hard work pays off and to never give up in pursuit of our dreams. Now, as a working mom myself, I have a level of admiration and appreciation for her that I could not have had before – she is truly a pillar of strength and the most selfless person I know.
Tori Abbott: My stepmother. She has never stopped learning or chasing after the next challenge. She has multiple degrees in business and accounting, a master’s in business, and is a Registered Nurse (RN), all of which were achieved while raising a young family and working full time. Thanks to her tireless efforts to motivate me as a young kid, I was the first person in my family to go to college and earn a degree (there have been many more since)!
Meagan Flanagan: My mom! She started out in Human Resources (HR)/Recruiting 20 years ago. She is the strongest, hardest-working woman I know. She has also reminded me that it is important to always look for ways to leave the space you are in better than when you got there. I try to do this by mentoring and coaching more junior professionals to learn from the mistakes I have made along the way.
Joely Bertram: I have to say my grandmother (or as I call her, Baka, which is Croatian for grandmother). Her whole life inspires me – how she immigrated to this country as a young child not knowing a word of English, graduated valedictorian from her high school, and won “Teacher of the Year in Lake County” during her career. She has traveled the world, worked hard to provide for her family, and has made endless connections with others. She took care of my sister and me growing up while my parents were at work and taught me so many lessons in confidence, self-sufficiency, and kindness. Every time I talk with her now, she always asks how I’m doing at work and what exciting things I am up to. Needless to say, I would not be the woman I am today without her.
3. What is one piece of advice that has greatly impacted you and your career trajectory?
Jessi Widhalm: Lead from where you are. This pivotal piece of advice was given to me by a mentor when I was serving as a young professional on Capitol Hill. In professional settings, I often felt discounted because of my age, which I felt translated to a lack of experience. While I held senior positions early in my career, I was often challenged by “imposter syndrome” or feeling like I did not belong. When I shared this sentiment with my mentor, he told me to try and overcome these feelings by finding unique ways to display the talents and value I bring to the table for both my bosses and my colleagues. This advice taught me that leadership is not defined by your title or position but rather by your ability to interpret, understand, and influence the direction of your organization, team, and/or project based on your unique experience(s) and the value that you can bring to a situation. The bottom line is that leadership is a choice you make, not a place you sit.
Tori Abbott: Go for it – do the absolute best you can, and then do a little more. Self-doubt is the biggest career killer. Just go for it and take a chance, especially if someone is willing to take a chance on you. Just because you cannot see “it” in yourself does not mean it is not there.
Meagan Flanagan: Show as much respect to the janitor as you would the owner of the company. Every person deserves dignity and respect. I think this is why Hagerty is successful. We step in when people are at the worst times of their lives, and the work we do makes a real difference.
Joely Bertram: A mindset that has stuck with me and led me to great experiences is being open to possibilities, more specifically, “limit how often you say ‘no.’” Of course, this excludes when you feel truly uncomfortable or unready for something, but I have found saying yes more often than saying no in this line of work has led me to great opportunities. One of these opportunities was my deployment to Lee County, Florida, after Hurricane Ian in 2022. I had never deployed before, nor had I worked on the Response side of things, but I knew I could learn and grow a lot from something like this. I consider this deployment to be one of the most exciting and important times for me while at Hagerty. That is due to the connections I made while embedded in the County Emergency Operations Center (EOC), learning to be flexible and empathetic with clients in all situations and seeing the impacts on the community first-hand. I wouldn’t have had these amazing experiences and learning moments if I hadn’t said ‘yes.’ By limiting how often I say ‘no,’ I have also gotten the opportunity to speak more in client-facing meetings, push the boundaries of my creativity to deliver amazing exercise products, and make new meaningful relationships within and outside of Hagerty.
4. What have been the most useful tools for developing your confidence as a professional and in the emergency management industry?
Jessi Widhalm: When I joined FEMA, I told the congressman I worked for that I was looking forward to having a job that ran at an easier pace. A few weeks into my new position, I wrote to him and laughed, saying I was naïve to think that would be true. Emergency managers wear so many different hats and are often called upon to find ways to solve problems that our unique skill sets lend themselves to. As a result, I have found that the best way to learn as an emergency manager is through hands-on experience – giving you an opportunity to understand the practical implications of the concepts, doctrine, legislation, rules, and regulations governing our industry while also allowing you to build relationships that continuously improve the delivery of services. In an industry that is always evolving, it is difficult to stay on top of every change, but with practical experience and colleagues to call upon, you are better positioned to come up to speed quickly and overcome the next challenge you may face.
Tori Abbott: Finding the value in the work I do makes it easy to want to excel at it and continually better myself in this industry. There are so many resources available, both internally at Hagerty and in the emergency management industry at large, which allow you to fully immerse yourself and learn the ins and outs of the industry at your own pace. Reaching out, having conversations, and building relationships with our technical teams to really understand how our consultants operate in the field are paramount to my work. The why is just as important as the how!
Meagan Flanagan: Do it, do it scared. Confront your imposter syndrome. No matter how much education and training you have, nobody really knows what they are doing until they have had some practice doing it. Even if you are scared, do it until you feel confident about doing what you are doing. Then, teach others what you have learned to keep the team moving forward.
Joely Bertram: There are a couple of tools that stand out to me. The first is Hagerty-centric, but it is career management! All my career managers (CMs) have taught me something unique and have built up different strengths in me. I truly feel that having a built-in advocate has made me so much more confident and has allowed me a space to talk through solutions or brainstorm without the pressure of immediately presenting to a client or building a deliverable. A huge shoutout to Liz Foster, Senior Managing Associate in Hagerty’s Preparedness Division and my current CM, for always making the time for me and letting me navigate my concerns and questions in a safe environment! Another tool specific to emergency management is the Homeland Security Exercise and Evaluation Program (HSEEP)! You do not realize how much of it is baked into our projects, client conversations, and overall exercise designs. Having a solid foundational knowledge of HSEEP has allowed me to align deliverables to it and helped me think outside the box, especially when a client has direct requests unbound by HSEEP principles. I think my favorite thing about HSEEP, however, is the recommended meeting structures/timelines and aligned documents for each type of exercise!
5. What are some fun and fulfilling ways you unwind after the workday ends?
Jessi Widhalm: As a stepmom of two and an expectant mother, these days, most evenings are spent on the go with activities! Despite hectic schedules, we aim for nightly family dinners, and I love to cook/bake, so you will typically find me finishing dinner preparations after work. I am also an avid Peloton member and I prioritize spinning, strength, stretching, and/or walking workouts daily (Robin Arzon is my favorite instructor). I also live at the beach, so I enjoy spending as much time as possible outside and on the water.
Tori Abbott: I love nothing more than being outside with my chickens and piddling around in my garden. When the weather is right, you can find me on a boat most days fishing with my husband and son or just enjoying being out on the water. My father is a charter captain, and most of my family still works on the water. I grew up on boats, and being on the water will forever be my happy place and saving grace.
Meagan Flanagan: I walk with my two-year-old every day after work. Watching him figure out the world really humbles me and helps me see the beauty in a lot of simple things. In the work we do, it is easy to overthink everything. When I am out with my son, I stop and take the time to see how joy can be had with puddles and sticks. I had no idea how much fun simple things can bring you if you just stop, take a breath, and be in the moment. I try to incorporate this into my work, treating each person I talk to as the most important thing in that moment. Yes, multi-tasking is necessary sometimes, but you can also complete a lot if you just finish what you start before moving on.
Joely Bertram: Either before or after a workday, I enjoy hiking. I am lucky enough to live around an abundance of national and state parks, mountains, rivers, and historical sites here in Northern Virginia. And if I cannot make it out to one of them, I am directly next to the Washington/Old Dominion Trail, which is the perfect walking spot if you just need to clear your head. Related, I also love traveling and learning new languages. Nothing is cooler than traveling to another country and getting to speak with locals in their native language. My last international trip to the Patagonia region of South America combined all of these: hiking, traveling abroad, and getting to practice my Spanish. It was one of the best experiences I have ever had and one more item I got to cross off my very long travel bucket list!
To learn more about Hagerty’s diverse and innovative professionals, visit Our People page.
Jessi Widhalm is a strategic communications and external affairs professional with over a decade of experience. Prior to joining Hagerty, Jessi served as Director of External Affairs for FEMA, where she was the agency’s senior spokesperson and principal liaison with the US Congress as well as our nation’s state, local, tribal, and territorial (SLTT) elected leaders.
Tori Abbott is an emergency management professional with 15 years of experience as a proposal manager and writer. At Hagerty, she oversees the proposal team and leads proposal development and coordination. She was also formerly certified as a Wilderness First Responder and Search and Rescue in both cave and water rescue.
Meagan Flanagan is a dedicated Managing Associate and a strong asset to the Talent Acquisition (TA) team. In support of Hagerty’s recruitment efforts, Meagan’s responsibilities include identifying the right full-time professionals and consultants to support the needs of our projects and clients.
Joely Bertram is an Associate in Hagerty’s Preparedness Division. Joely has experience assisting with standard operating procedures, security and threat preparedness, planning exercises, and cybersecurity policy. At Hagerty, she has also worked on research and analysis pertaining to proposals and comprehensive emergency management plans.