Jeb Stephen CLF®

Partner and Financial Planner

Jeb began his career in financial services in 2002 after a successful career in real estate. As a University of Akron graduate in organizational supervision and a lifelong resident of Northeastern Ohio, Jeb has also earned his CLF designation, the only designation in the financial services industry geared specifically towards leadership. Jeb spent the majority of his early years in the industry in career management where he managed both teams and agencies for Western & Southern Financial Group, Mutual of Omaha, and MetLife Premier Client Group as a Managing Sales Director before the transition to Skylight Financial Group.

During his time in leadership, Jeb has been recognized for receiving multiple *GAMA International Silver level Frontline Leaders Awards (2010-2014), Medallion Club at W&S Financial Group (2005), multiple Field Management (2010, 2011, 2014) and the Levels of Distinction Awards with Mutual of Omaha (2013, 2014).

When Jeb made his transition to Skylight Financial Group in 2017, he and his business partner Brent Affolter, decided to step away from leadership and partner together in building a practice to exclusively work with their clients.  Jeb and Brent who are also lifelong friends, now look back at their decision to partner together and start their business as one of the best business decisions they have made.  Since starting their practice, they have both qualified consecutively for the Massachusetts Mutual Life Insurance Company’s (MassMutual) Leader’s Meeting status (2018-2020), as well as Million Dollar Round Table (2018-2022), which is recognized internationally as the industry’s standard of excellence. 

As a resident of Cuyahoga Falls, Jeb enjoys golfing, boating, snow skiing, and cooking. Jeb and his wife Jill are proud parents of their two children Trevor, and Amelia, and Jeb’s two children Dawson, and Lauren.

*This award was issued by GAMA International in March 2010, 2011, 2013, 2013, and 2014 based on the prior calendar year. A fee was paid to be considered for this award.  MassMutual provided monetary support to GAMA International to help fund certain events and programs. MassMutual employees and/or agents are not involved in the nomination and selection process.

Douglas Jeb Stephen is a registered representative of and offers securities, investment advisory, and financial planning services through MML Investors Services, LLC.  Member SIPC. OSJ: 1956 Carter Road, Suite 200, Cleveland, OH 44113. 216.621.5680. CA Insurance License #402944.

State of Domicile: OH

Featured News Stories:

Picture of Jeb Stephen, CLF®

Contact Jeb Stephen CLF®