Jen Dawson, CFP®

Owner and Managing Director

Jen Dawson helps clients get crystal clear about what’s most important in life, and then helps them feel confident and connected to the financial plan that supports their vision. Jen asks great questions and creates spaces for critical conversations that are often neglected by busy professionals. She advises clients well beyond just portfolio management, with a focus on financial freedom scenarios, college funding tactics, tax reduction strategies, and proactive planning ahead for worst case scenarios, such as death or disability. For almost twenty years, Jen has been helping clients have a great relationship with their money, offering a unique blend of financial expertise and a sensitivity to the emotion and complex undercurrents linked with money conversations.

In addition to her primary role as wealth manager for her clients, as an owner, Jen is responsible for Hemington’s expansion in Chicago. Jen’s specialty in working with lawyer clients has made Hemington a valuable resource for Chicago’s legal community. Jen co-authored Hemington’s white paper, What Do Breadwinner Women Lawyers Want? and writes and speaks often about how to better serve the very specific needs and wants of lawyer clients. Jen is on a personal mission to bring more financial peace of mind and joy to lawyers, a group of professionals who are under huge amounts of stress, professionally and personally.

Jen is also a wholehearted champion of women and girls. She is passionate about empowering the women in her life through financial education, strategic networking, and by creating space for new perspectives and discussions about women’s issues. She hosts regular events for women in Chicago and is a frequent speaker and writer about women of wealth and personal finance. Jen is also a past Board President for Girls on the Run Chicago, a non-profit after-school program that inspires girls in the Chicagoland area to be joyful, healthy and confident using curriculum that teaches life lesson while training for a 5k.

Jen graduated from University of South Carolina’s Honors College Summa Cum Laude with a degree in Mathematics and was an Academic All-American and captain of USC’s NCAA National Championship Track & Field team. She earned her Certified Financial PlanningTM designation through Northwestern University. She is a member of the Chicago Estate Planning Council, a co-founder of the Women’s Initiative Mentorship Program for The National Association of Personal Financial Advisors (NAPFA), a 9-time winner of the Five Star Professional Wealth Manager award1, and a Forbes/SHOOK Best-in-State Top Women Wealth Advisor2.

Jen lives in Bucktown in Chicago with her husband and sons. On any given weekend, you can find her running on the 606, squeezing in a yoga class, or planning their family’s next travel adventures.

Recent Recognition & Publications

  • Featured in the Discover|Modern Money article, “How to Save More Money in the Stay-at-Home Economy by Focusing on What Matters Most.”
  • Authored the article, “What are you Looking Forward to Right Now?”, which was featured in the Women’s Bar Association of Illinois newsletter, 38-9.
  • Featured in the New York Post’s article, “Dream up your definition of success for a rewarding career.”
  • Her article, “Building a Niche Practice: Don’t Be Afraid to Get Even More Specific,” was the August 2019 cover story for The National Association of Personal Financial Advisors’ monthly publication, NAPFA Advisor, The Art and Science of the Fee-Only Practice. Jen highlighted the ways that Hemington’s specialization in serving women lawyers benefits clients and helps to eliminate competition, increase referrals, and provide greater clarity in business strategy. Jen was a speaker on this same topic at NAPFA’s National Conference in October 2019.
  • Featured in Above the Law’s Podcast, “Are You a Woman Fed Up with BigLaw? You Aren’t Alone.”
  • Featured in The Resilient Lawyer’s Podcast, “Removing the Taboo with Money and Finding Balance Financially.”
  • Featured in The Dispatch-Argus after crossing the finish line at the Tokyo marathon on March 3, 2019, completing all six World Major Marathons and raising over $50,000 for the nonprofit organization, Girls on the Run-Chicago.

email: [email protected]
Phone: 312.757.5339


1. Issued on 10/17/23 by Five Star Professional (FSP) for the time period 1/9/23 through 7/31/23. Compensation was not provided directly or indirectly by the adviser in connection with obtaining or using the third-party rating.

2. Issued on 2/8/24 by Forbes/SHOOK for 2024. Advisor rankings were compiled by SHOOK Research, which uses financial data and interviews candidates nominated by their firms. Compensation was not provided directly or indirectly by the adviser in connection with obtaining or using the third-party rating.