Reiley Crosby, CRPS™, AIF®

Partner & Senior Financial Advisor

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Experience & Expertise

Reiley is a Partner & Senior Financial Advisor in Greenspring’s Institutional Consulting Group. Reiley strives to help companies and organizations develop effective strategies for their retirement plans, improve efficiencies, reduce costs, and ultimately guide employees toward successful retirement outcomes. He earned the Chartered Retirement Plans Specialist℠ designation by completing a comprehensive course of study that encompasses 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.

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Favorite Thing About Working With Clients

“My favorite part of working with clients is meeting and interacting with so many great people. I’ve been fortunate to build numerous meaningful and impactful relationships with them. The opportunity to provide significant value to both plan sponsors and their employees—and to witness the long-term impact—is the most rewarding aspect of my job.”

My Philosophy On Client Service

“My philosophy on client service is to always try to be proactive, addressing potential challenges before they arise, and delivering solutions that align with my clients’ long-term goals. I believe being proactive is key to building trust, strengthening relationships, and ensuring my clients feel valued and supported.”

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.
Monkton, MD
Dickinson College
BHB Memorial Foundation
All of our non-profit clients making an impact in their communities
Golfing
Snowboarding
Baltimore Ravens and O's
Spending time with family and friends
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.”

Recent Insights

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The 2024 PLANADVISER Emerging Leaders was awarded to Reiley Crosby, Christian Stanley, and Casey Crawford on 8/19/24 based on the time period of the year prior and is given to members of the retirement plan advisory industry whose managers and peers believe are poised to advance the profession in the future. To be considered, potential recipients must be nominated and have worked in the retirement plan advisory industry for at least three years, but no more than 10. The award is open to individuals across all areas of the business—advising, operations, client relations, data, participant education, etc. Greenspring compensated Plan Advisers a fee to utilize the logo, however Greenspring Advisors did not pay to participate in the award nominations. Greenspring Advisors has a reasonable basis for believing that any questionnaire or survey used in the preparation of this third-party rating is structured to make it equally easy for a participant to provide favorable and unfavorable responses and is not designed or prepared to produce any predetermined result. 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. The . The 2024 AdvisorHub Next Gen Ranking was awarded by AdvisorHub on June 20th, 2024 based on the time period of the year prior. It was awarded to Reiley Crosby, CRPS®, AIF®. Greenspring Advisors did not pay to participate. Greenspring Advisors has a reasonable basis for believing that any questionnaire or survey used in the preparation of this third-party rating is structured to make it equally easy for a participant to provide favorable and unfavorable responses and is not designed or prepared to produce any predetermined result. 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. 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. It was awarded to Matt Cellini, Reiley Crosby, and Christian Stanley. Greenspring Advisors compensated NAPA through a paid membership, however Greenspring Advisors did not pay to participate in the award nomination. Greenspring Advisors has a reasonable basis for believing that any questionnaire or survey used in the preparation of this third-party rating is structured to make it equally easy for a participant to provide favorable and unfavorable responses and is not designed or prepared to produce any predetermined result. 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. 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 compensated NAPA through a paid membership, however Greenspring Advisors did not pay to participate in the award nomination. Greenspring Advisors has a reasonable basis for believing that any questionnaire or survey used in the preparation of this third-party rating is structured to make it equally easy for a participant to provide favorable and unfavorable responses and is not designed or prepared to produce any predetermined result. 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.