Her Story
About Bobbi
Bobbi Maroney is a Senior Executive Assistant to the CEO in the tech-enabled insurance industry, with nearly two decades of experience spanning financial services, business analytics, and strategic operations.
Her career began at Brown Brothers Harriman in Boston, where she spent more than seven years building operational discipline. She later joined Dealer.com as a Business Performance Analyst, developing executive-level reporting, Tableau dashboards, and cross-functional problem-solving skills that eventually led her into executive support. After several years supporting senior leadership at Cox Automotive, she joined Polly, where her role extends well beyond traditional executive assistance.
At Polly, Bobbi serves as a communications partner, logistics architect, culture builder, and relationship manager, helping translate the CEO's vision into coordinated action across the organization. She manages the company intranet, leads weekly all-company communications, develops company-wide learning experiences, and coordinates executive offsites and leadership summits. Known for her emotional intelligence and ability to lead without formal authority, she thrives at the intersection of strategy and execution. She holds a Level 1 Chief of Staff certification through The Chief of Staff Association and is intentionally developing toward that role as her next chapter.
Beyond work, Bobbi is deeply committed to her community. She serves on the Board of Directors of the Boys & Girls Club of Burlington, Vermont, where she has led engagement and fundraising efforts, including serving as the pitch person at the organization's Great Futures Luncheon, which exceeded its fundraising goal. She has been recognized as the organization's Most Successful Ambassador and Table Captain Champion.
Bobbi credits her parents and her own persistent drive for much of her success. She strongly encourages others to say yes to opportunities that promote growth, and grounds her professional philosophy in trust, candor, accountability, and consistently showing up for the people around her.
Her Interview
Ten minutes with Bobbi
01What do you attribute your success to?
I attribute much of my success to the example and encouragement of my parents, who have been motivating influences throughout my life. I believe I inherited my drive from both of them, along with an internal desire to continually pursue goals that may initially feel out of reach. That mindset has encouraged me to keep learning, embrace challenges, and continue moving forward even when the path is uncertain.
02What’s the best career advice you’ve ever received?
The best career advice I've lived by is to remain open to opportunities, take calculated risks, and be willing to step outside of your comfort zone. My own career has shown me how an unexpected opportunity can become the foundation for an entirely new professional path. I have learned to embrace uncertainty, remain curious, and approach new responsibilities as opportunities to expand my knowledge and capabilities.
03What advice would you give to young women entering your industry?
My advice is simple: say yes. If an opportunity presents itself and you are scared, uncertain, or unsure whether you are completely ready, take the leap when it aligns with your goals and desire to grow. Be willing to expand your horizons, develop a genuine thirst for knowledge, and look for opportunities where you can learn by doing. I also believe in being the person who notices what needs to be done and takes ownership of getting it done well. Few things are more rewarding than a genuine sense of accomplishment.
04What are the biggest challenges or opportunities in your field right now?
I see a significant opportunity in the continued evolution of the Executive Assistant role into a more strategic business partnership. Today's executive support professionals can contribute well beyond traditional administrative responsibilities by translating leadership vision into execution, strengthening communication, coordinating across functions, supporting organizational culture, and influencing outcomes without formal authority. For me, this evolution represents an opportunity to develop the capabilities required for a Chief of Staff role and broader strategic leadership.
05What values are most important to you in your work and personal life?
Trust, candor, consistency, relationships, accountability, curiosity, and service are central to how I approach both work and life. I believe strong professional relationships are built through trust and consistently showing up for others. I value being a safe, dependable partner while also having the determination to follow through on my commitments. I am also deeply motivated by meaningful community impact, which is reflected in my involvement with the Boys & Girls Club of Burlington.
Join Influential Women and start making an impact. Register now.