Women have been narrowing gaps and breaking ceilings for decades—though of course, there’s still more left to narrow and break.¹ Girls are excelling in science, technology, engineering, and math (STEM) subjects, and more and more women are taking over family finances and investments.² And in the next decade, women are expected to have control over a sizable portion of baby boomer financial assets. 

And yet, despite all these changes, fewer than one in five financial advisors is a woman.³ As more clients ask to work with a female advisor, advisory firms need to be sure they’re doing what they can to attract women to the profession.

With these trends affecting such a critical player in the industry, we wanted to learn more about the role of the retirement plan advisor and how to attract more women to the profession. Christine Bowmaster, John Hancock Retirement’s director, field effectiveness, spoke with three women who have built successful careers in the field: 

• Jamie Greenleaf AIF®, CBFA, C(k)P®, CHSA, Lead Advisor and Principal, Cafaro Greenleaf
• Kathleen A. Kelly, AIFA®, CRPS®, Founding and Managing Partner of Compass Financial Partners, LLC
• Tina Wisialowski, CRPS®, Associate Vice President, Wealth Management, Senior Institutional Consultant, Corporate Retirement Director, Morgan Stanley

Many people think of financial advisors as being focused on investments—and in many cases, that’s true. But the role of a retirement plan advisor is more nuanced, with a focus on helping people—helping plan sponsors, as well as participants. And that’s ultimately what led all three women to their careers, although they each got there through a different route. 

Although Jamie’s mother was a true trailblazer in the business—founding what’s now Cafaro Greenleaf in 1981—Jamie didn’t start out wanting to be a financial advisor. She started out in Smith Barney’s training program but found the broker side of the business “too transactional.” That’s when her mother suggested she join the family business, “talking to people about saving for retirement.”

Tina’s first job after college was in a training program for a trust company, during which she worked on retirement plan conversions. After a few other retirement-plan-related jobs, she applied for an advisor position, thinking “this is the perfect fit because it combines everything that I had done in the past into one role, and I can really guide client sponsors and still work with participants if I choose.” 

Kathleen, on the other hand, decided to be a financial advisor right out of college, as she was “really attracted to the entrepreneurial aspect of building my own practice," it aligned with her interest in financial topics, and she “loved the idea of being able to work with people and help them financially."

All three women agreed that no two days are alike, because the job of an advisor includes so many “customers”—plan sponsors and their employees—and so many skill sets. On any given day, they’re called on for a range of duties, both in the office and on the road: 

• Sales and business development
• Client service, reviews, and strategy
• Investment review and management
• Employee communications and education

All three women agreed that keeping up with industry reading was an important daily task. Jamie starts each day reading up on the industry—including other HR benefits—so she can “keep clients ahead of where things are going.” And Kathleen confirms the importance of honing her skill set and continual learning through reading and conferences, as “you never know when a little nugget will come in handy with a client.”

What came through loud and clear is the passion these women have for what they do, their perseverance in building up a business, and the laser focus on customer care that led them to the success they’ve enjoyed. 

In addition to a passion for helping people, here’s what they look for in advisor job candidates:

• Problem solving skills
• Persistence
• Resilience
• Able to focus on the details 
• Compassion 

As for the scarcity of women advisors, Jamie, Kathleen, and Tina see the number of women in the field growing. They share the aspects of the job that can appeal to women, as well as why women—as well as men—can be successful in the role.

In spite of improvements in gender equality and role balancing at home and the office, women still bear the brunt of home and family work, even when both spouses are working.⁴ One of the aspects of the job Kathleen thrives on is the full calendar—"when I look at my calendar and it’s back to back to back, I like it that way.” But at the same time, she said that it also allows for the flexibility that she needs as a mother. “This has been a perfect career for being able to balance” the responsibilities of managing home life and building a business.

Jamie also mentioned that traditionally, women were thought of as "nurturers." And while that may not be true for all women, “listening and nurturing” are critical skills for an advisor to master. “Planning for retirement isn’t just smooth sailing … what we do is of course financial in nature”, but it’s also about helping clients and employees focus on the long term and “giving them the ability to take the baby steps” to get there. 

They also all agreed that the gratification they receive by seeing people saving and retiring well makes the job worth it. Tina’s perspective is that “ … quite honestly, a lot of employees don't understand just the basic concepts of finances and saving for retirement.” Jamie agreed, saying that she’s been working with a lot of the same employees for 20 years, and when “they come up and say thank you, I have more money than my house is worth and I can take a trip to Alaska or see my grandkids … that’s what gets me excited every morning.” 

Meet the advisors

Jamie Greenleaf AIF®, CBFA, C(k)P®, CHSA, Lead Advisor, Principal

Cafaro Greenleaf

A recognized expert in the retirement plan industry, Jamie has been with Cafaro Greenleaf since 1993 and a principal since 1997. She has been a recognized vice president and retirement plan advisor with UBS Financial and with Prudential Securities, consistently ranking among the top retirement advisors nationally at both firms.

Jamie is regularly invited to speak at industry conferences and is a sought­ after presenter for many other advisor and plan sponsor continuing education sources such as Pensions & Investments, HR.com, and SHRM University Conference Services. Jamie serves on the Advisory Boards of Prudential, and John Hancock, as well as the Leadership Council for the National Association of Plan Advisors (NAPA), where she regularly provides her retirement plan expertise and experience to our nation’s regulators and policymakers in Washington, D.C.

Jamie has spent her entire professional career helping retirement programs and public funds. She has provided consulting services in all areas of plan management and oversight, including plan design, fees and services benchmarking, investment management selection and monitoring, fiduciary and regulatory compliance, investment policy design, and financial education to many Fortune 500 and publicly traded companies, nonprofit entities and public agencies.

She is an adjunct lecturer in the Plan Sponsor University certification program for UCLA’s Anderson School of Business-Executive Education. Greenleaf holds a BA in Business Administration from Delaware Valley College, is a Registered Financial Advisor and is Life insurance licensed. Jamie is also is a Registered Investment Advisor representative and holds Series 7, 26, and 63 licenses.

Jamie is known for her extensive and unparalleled knowledge, expertise and passion for the industry. She has a keen ability to guide, support and educate plan trustees, plan sponsors and plan participants alike. Leading from our headquarter office in Red Bank, New Jersey, Jamie advises throughout the New York Metropolitan and Tri State areas, traveling to other regions of the country when the opportunity to serve arises. She is an IMPACT 100 Jersey Coast member, an organization that funds transformational grants to Monmouth County, NJ nonprofits yearly. Jamie currently resides in Rumson, NJ with her husband and two sons.

Kathleen A. Kelly AIFA®, CRPS®, Founding and Managing Partner

Compass Financial Partners, LLC

Kathleen Kelly, originally from Ballston Lake (Saratoga County), New York, received her Bachelor of Arts degree in Economics from Wake Forest University. She is a Founding and Managing Partner of Compass Financial Partners, LLC, and a 25-year veteran of the financial services industry, specializing in the areas of retirement plan consulting & investment advisory services for qualified retirement plans and executive benefit planning. Kathleen has achieved the Chartered Retirement Plan Specialist (CRPS) designation, and the Accredited Investment Fiduciary Analyst (AIFA) designation through the Center for Fiduciary Studies. A nationally recognized firm, the team at Compass Financial Partners was named to Barron's 2015 inaugural ranking and 2018—2020 listing of Top Institutional Investing Consultants,⁵ the 2013—2019 Pension & Investments Top Consulting listing,⁶ the PLANADVISER 2013—2018 & 2020 Top 100 Retirement Plan Advisers listing and was selected as a finalist for the 2015, 2016 and 2017 PLANSPONSOR Retirement Plan Adviser Team of the Year Award.⁷ Additionally, she represented Compass Financial Partners as the recipient of the “2014 401(k) Advisor Leadership Award” (sponsored by NAPA/ASPPA).⁸

In further recognition of Kathleen’s leadership within the retirement plan consulting community, she has been selected to serve on the Empower Advisory Board, Nuveen Retirement Leadership Council, Principal Financial Professional Advisor Council, the Prudential Advisor Council, the MassMutual Retirement Partners Council, the Transamerica Retirement Solutions RIA Advisory Board, the JP Morgan DC Advisor Council, the Fidelity Workplace Investing Advisor Council, and the Retirement Advisor Council. She is a frequent speaker at industry conferences and regularly quoted in trade publications.

Active in her community, Kathleen was appointed by the University of North Carolina Board of Governors to the Board of Trustees for Winston-Salem State University where she serves as Vice-Chair of the Board, and serves on the Advancement Committee; the Finance Committee; and Chairs the Governance, Advocacy, Trusteeship and Ethics Committee. Additionally, she has served on both the Wake Forest Board of Visitors and Greensboro College Board of Visitors. She was awarded a “Women in Business” Award (based on successful entrepreneurship) through the Triad Business Journal, and was named a “2019 Women of Distinction” by the Peaks to Piedmont Girl Scout Council for making a difference in the community, where she served as a past Board member. Other community involvement has included work with Operation Smile, founding membership in the Steering Committee for Women’s Programming with the Greensboro Chamber of Commerce, and her current position on the United Way of Greater Greensboro’s Tocqueville Strategy Team and Canterbury School Endowment Committee. Kathleen also completed her one-year term as the 2011 American Heart Association Guilford Heart Ball Chair, having achieved both fundraising and attendance numbers representing new records. In her spare time, Kathleen enjoys playing golf and tennis and spending time with her husband, two children, and golden retriever.

CRPS conferred by College for Financial Planning

Tina Wisialowski, CRPS®, Associate Vice President, Wealth Management, Senior Institutional Consultant, Corporate Retirement Director

Graystone Consulting, a business of Morgan Stanley

Tina Wisialowski has over 23 years investment and retirement plan consulting experience. She is a Senior Institutional Consultant and Corporate Retirement Director at Graystone Consulting, a business of Morgan Stanley, based out of Milwaukee, Wisconsin, office. As a Corporate Retirement Director, Tina focuses on retirement plan consulting, including the plan design, education and investment management of her clients’ plans. Tina serves on the advisory board for John Hancock and is an active member of the Retirement Advisor Council.

Prior to joining the Graystone Consulting Team, Tina was a Managing Director with Sheridan Road Financial in Milwaukee, Wisconsin, where she was responsible for the business development and management of client relationships throughout Wisconsin.

Tina is a graduate of the University of Wisconsin-Madison with a B.B.A. in Business Administration, with a double major in Finance, Investment, and Banking and Management. She was named as one of the National Association of Plan Advisors’ Top Women Advisors (November 2019, 2018, 2017, 2016, 2015)⁹ and one of the “Top 401 Retirement Advisors” by The Financial Times (2019, 2018, 2017).¹⁰ She was also named to the 2020 PLANADVISER Top 100 Retirement Plan Advisers. Tina holds her Series 6, 7, 63, and 65. In addition, she holds her CRPS® and AIF® designations. Tina lives in Oak Creek, Wisconsin, with her husband and two sons. She is very active in her sons’ activities and enjoys participating in CrossFit.

About the interviewer 

Christine Bowmaster, Director, Field Effectiveness

John Hancock Retirement 

In this role, Christine is a member of the sales and distribution leadership team, working with the field in support of recruiting, training, and diversity efforts. She also represents sales in product development and operations initiatives. Prior to this role, Christine spent 15 years as a regional vice president, leading sales and service teams for the western Missouri and Kansas territory. Christine has been with John Hancock for more than 16 years and in the retirement plan industry for 27 years. Before joining John Hancock, she was a retirement plan consultant for Marsh & McLennan, a Heffernan Group, and worked in external sales for another plan recordkeeper. 

1 "Report: Small Gains Made in Advisor Diversity," wealthmanagment.com, January 14, 2021.  2 “Women as the next wave of growth in US wealth management”, McKinsey & Company, July 29, 2020.  3 “Clients Want to Work With Female Advisers and Firms Are Taking Notice,” The Wall Street Journal, August 24, 2019. 4 "Women Still Handle Main Household Tasks in U.S.,” Gallup, January 29, 2020. 5 Barron’s evaluated a range of criteria to compile the list, including institutional investment assets overseen by each team, revenue generated by those assets, the number of clients served by the team, the number of team members and their regulatory records as well as advanced professional designations and accomplishments represented on the team. 6 Pension & Investments' consultant survey focuses on firms providing investment management consulting services. The assets under advisement are tracked for total clients worldwide, institutional clients and U.S. institutional, tax-exempt clients, as of June 30. Retainer and non-retainer clients may be counted in the AUA. 7 Individuals had to either serve 105 or more plans or have at least $750 million in AUA; teams needed to advise at least $2.25 billion in assets or a minimum of 145 plans; and multioffice teams needed to oversee $10 billion in plan assets or 400 or more plans. 8 Nominated and voted on by industry peers and selected by a NAPA panel of judges based on information about their practice, experience and accomplishments as provided by nominees. 9 NAPA Net's “Top Women Advisors of 2018,” November 28, 2018 as appearing in NAPA Net or www.Napa-Net.org, is based on nominations by the NAPA members. Nominees are asked to respond to a series of questions, both quantitative and qualitative, about their experience and practices. A panel of judges reviewed the anonymized questionnaires and selected the women honored in three categories: All Star, Captains, and Rising Stars.  The rating is not indicative of the Financial Advisors' future performance. Neither Morgan Stanley Smith Barney LLC or its Financial Advisors paid a fee to NAPA-Net in exchange for the rating. 10 The Financial Times 401 Top Retirement Advisors is an independent listing produced annually by the Financial Times (September 2019). The FT 401 is based on data gathered from advisors, regulatory disclosures, and the FT's research. The listing reflects each advisor's status in six primary areas: DC plan assets under management (AUM), DC AUM growth rate, specialization  in DC plans, years of experience, advanced industry credentials and compliance record. This award does not evaluate the quality of services provided to clients and is not indicative of the Financial Advisor's future performance.  Neither Morgan Stanley Smith Barney LLC nor its Financial Advisors or Private Wealth Advisors pays a fee to The Financial Times in exchange for the rating.