PLANADVISER: Tell us about your role at your firm and how you contribute to its growth and progress. How did you end up there?
Dolan: At Creative Planning, I’m the main point of contact for my clients, supporting the day-to-day administration of their retirement plans. I answer questions from HR teams, offer ongoing guidance and meet with retirement plan committees to review investments, regulatory updates and industry trends. Building strong, trusted relationships is something I’m proud of. It’s helped keep clients engaged long-term and has even led to new business through word-of-mouth.
My career path wasn’t exactly traditional. I started college as a pre-vet major, and through a friend of a friend, landed an internship on the Lockton Retirement team without any idea how retirement plans worked. I quickly found myself drawn to the collaborative culture, the team I worked with and the constantly changing nature of the industry.
Eight years later, I’m still with the same team, now part of Creative Planning, and just as excited as I was on Day 1. I love the impact we make, the trust we earn and the chance to work with people who genuinely care about helping clients succeed.
PLANADVISER: What steps do you think will help improve the retirement industry and participant outcomes in the future (particularly ways in which your firm can help with that progress)?
Dolan: Improving participant outcomes starts with meeting people where they are. Creative Planning understands that and has made real investments in personalized support, making sure participants at all income levels have access to guidance. A lot of people assume that financial advice is just for high earners, which can stop others from even asking for help. Creative Planning is working to change that mindset.
Starting my career in this industry right out of college gives me a different perspective. Many of my college peers still don’t fully understand why saving for retirement matters or feel overwhelmed by it—and honestly, I’d probably feel the same way if this wasn’t my day-to-day. Hearing their questions and concerns helps me understand the real challenges participants face and what HR teams hear from their employees. I bring those insights into my daily work and work with HR teams and committees to either improve conversations or implement plan design features to help employees.
PLANADVISER: Have you had mentors or role models? Who are they and what lessons have you learned from them?
Dolan: Jessica Stephan has been one of the most influential mentors in my career. She was one of the first employees in the Lockton Retirement practice and now serves as the senior practice leader at Creative Planning. I’ve had the opportunity to work alongside her from the start of my internship through to today, where we now share ongoing client management responsibilities.
Jessica leads by example, and I continue to learn from her every day—whether it’s how she engages with clients or communicates with peers. One of the most important lessons she’s taught me is the value of advocating for yourself in every room you walk into. This business involves a lot of personalities, and I’m still learning how to navigate that—how to engage with different people and areas of expertise while staying true to myself. Jessica has helped me see that it’s possible to do both. She takes the same approach to advocating for her clients, never stopping until she finds the right solution.