Reiley Crosby, CRPS™, AIF®

Partner & Senior Financial Advisor

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Experience & Expertise

Reiley is a Senior Financial Advisor in Greenspring’s Institutional Consulting Group. Reiley strives to help companies develop strategies in their retirement plans to drive efficiencies, reduce costs, and ultimately guide employees to successful retirement outcomes. He does this by serving as a fiduciary to all clients, developing repeatable and documented processes, and providing independent advice from the client’s side of the table. He earned the Chartered Retirement Plans Specialist℠ designation by completing a course of study encompassing the design, installation, maintenance, and administration of retirement plans. He has also earned the Accredited Investment Fiduciary® professional designation awarded by the Center for Fiduciary Studies and has received formal training in investment fiduciary responsibility.  Reiley previously worked at RBC Wealth Management where he serviced corporate retirement plans and participants.

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Favorite Thing About Working With Clients

“I enjoy taking responsibilities and tasks off of our clients’ plates so they can focus on running their businesses.”

My Philosophy On Client Service

“I know I am doing my job well when I can deliver answers, insights, and materials to clients before the client necessarily has to ask for them. The less time a client has to focus on addressing issues with their corporate retirement plan the better I consider my performance.”

Maryland 
B.A. from Dickinson College
Chartered Retirement Plans Specialist℠
Accredited Investment Fiduciary®
2024 PLANADVISER Emerging Leader
#1 in AdvisorHub’s 2024 1,000 Advisors to Watch, Next Gen category
NAPA's 2024 Aces: Top 100 Retirement Plan Advisors Under 40
NAPA's 2025 Aces: Top 100 Retirement Plan Advisors Under 40

Please see below for award disclaimers.
Baltimore, MD
Dickinson College
Cal Ripken Sr. Foundation
Golfing
Snowboarding
Playing volleyball
Have a Bias Towards Action
What I Love About Greenspring

“I love the working culture that has been instilled at Greenspring. Everyone is committed to success and providing a superior service for clients, and we have a good time together while we do it.”

Greenspring News

Greenspring Advisors Named as Top Defined Contribution Advisor Team in Nation | Top 3 in Maryland

Greenspring Advisors, an independent, fee-only Registered Investment Advisor (RIA) named one of the nation’s top defined contribution (DC) Financial Advisor Teams by NAPA.

Greenspring Advisors Awards $50,000 in Grants

The 2024 PLANADVISER Emerging Leaders ranking was awarded by PLANADVISER on August 16th, 2024, based on the time period of the year prior. This award is based on nominations received by PLANADVISER and self-nominations are accepted. It was awarded to Reiley Crosby, CRPS™, AIF®, Zack Hubbard, CFP®, Christian Stanley, CRPS™, AIF®, NQPC™, and Casey Crawford CRPS™, AIF®. Greenspring Advisors and our advisors did not pay to be considered for this award. The 2024 AdvisorHub Next Gen Ranking was awarded 6/20/24 by AdvisorHub to Reiley Crosby based on the time period of the year prior. Greenspring Advisors did not pay to participate. The 2024 AdvisorHub Next Gen Ranking was awarded 6/20/24 by AdvisorHub to Reiley Crosby based on the time period of the year prior. Greenspring Advisors did not pay to participate. The 2024 Aces: Top 100 Retirement Plan Advisors Under 40 was awarded by the National Association of Plan Advisors on November 14th, 2023, based on the time period of the year prior. This award is based on applications received from nominees designated by NAPA Broker-Dealer/RIA Firm Partner. It was awarded to Matt Cellini, Reiley Crosby, and Christian Stanley. Greenspring Advisors and our advisors did not pay to be considered for this award; however, Greenspring Advisors does have a paid membership with the National Association of Plan Advisors. The NAPA 2025 Aces: Top 100 Retirement Plan Advisors Under 40 was awarded by the National Association of Plan Advisors on November 18, 2024, based on the time period of the year prior. This was awarded to Matt Cellini, Reiley Crosby, and Christian Stanley. Greenspring Advisors and our advisors did not pay to be considered for this award; however, Greenspring Advisors does have a paid membership with the National Association of Plan Advisors. Third party rankings and recognitions are no guarantee of future investment outcomes and do not ensure a client or prospective client will experience a higher level of performance results.