Her Story
About Jamie
Jamie Greenleaf, AIF®, CBFA, C(k)P is the Founder and Lead Advisor of Greenleaf Advisors, co-founder of Fiduciary In A Box® (FIAB), and a nationally recognized fiduciary consultant with more than 30 years of experience helping employers strengthen governance and reduce fiduciary risk.
After building a successful career in retirement plan consulting, Jamie recognized that healthcare benefits had become one of the largest financial and fiduciary responsibilities facing employers. Today, she focuses exclusively on helping organizations establish prudent governance processes for their healthcare plans, improve transparency, control costs, and enhance employee outcomes through informed fiduciary decision-making.
Drawing on deep expertise in ERISA, the Consolidated Appropriations Act (CAA), and healthcare plan governance, Jamie advises employers on fiduciary oversight, vendor accountability, regulatory compliance, committee governance, and strategic plan management. Her mission is to equip plan sponsors with the education, tools, and practical processes they need to confidently fulfill their fiduciary responsibilities.
Jamie is also the founder of TILT and has founded several innovative organizations throughout her career. She began her career in the retirement industry, inspired by her mother, a respected pioneer in the profession, and has spent decades advocating for greater transparency and accountability in employee benefits.
A frequent national speaker, Jamie partners with organizations such as The Plan Sponsor University (TPSU) and the National Alliance of Healthcare Purchaser Coalitions to educate employers on healthcare fiduciary governance and emerging regulatory requirements. She is passionate about transforming complex regulations into practical, actionable strategies that help employers build stronger health plans while reducing organizational risk.
Jamie earned a Bachelor of Science in Business Administration from Delaware Valley University and completed professional studies in Behavioral Finance. She holds the Accredited Investment Fiduciary (AIF®), Certified Behavioral Finance Analyst (CBFA), and Certified 401(k) Professional (C(k)P) designations, along with FINRA Series 7 and Series 66 licenses and health and life insurance licenses.
Her Interview
Ten minutes with Jamie
01What do you attribute your success to?
I attribute my success to the example set by my mother, who was a true pioneer in our profession and inspired me to pursue excellence. Being the oldest of seven children also taught me responsibility, resilience, and the importance of caring for others. Throughout my career, I've remained bold, curious, and willing to speak up, embrace challenges, and continuously learn, which has allowed me to grow both personally and professionally.
02What’s the best career advice you’ve ever received?
The best career advice I've ever received is simple: "Keep going." Perseverance is essential because challenges are inevitable, but success comes from staying committed, maintaining enthusiasm for your work, and refusing to give up when obstacles arise.
03What advice would you give to young women entering your industry?
My advice is to be passionate about the work you choose because passion will help you overcome difficult moments. Stay true to yourself, embrace your unique strengths and even your perceived weaknesses as opportunities for growth, and never stop learning. Seek out mentors, collaborate with others, and remember that you don't have to navigate your career alone.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges is that many employers still do not fully understand the evolving regulations governing healthcare benefit plans or the fiduciary responsibilities that accompany them. At the same time, this creates an incredible opportunity to educate employers, improve transparency, help control healthcare costs, and enhance employee benefits through stronger governance and informed decision-making.
05What values are most important to you in your work and personal life?
I believe in staying true to myself, acting with honesty and integrity, and remaining open to change. I view change as an opportunity for growth rather than something to fear, and I strive to approach every challenge with authenticity, curiosity, and a willingness to learn.
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