Darryl Caffee in

Darryl Caffee

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SVP, Director of Retail Lending & Collections/CRA Officer at Webster Five
📍 Greater Boston, United States

Darryl is a results-oriented mortgage leader and licensed attorney serving as SVP, Director of Retail Lending & Collections at Webster Five. He has a proven track record of driving revenue growth and leveraging technology to enhance operational efficiencies. He holds a Doctor of Law from the Massachusetts School of Law and excels in regulatory compliance and lending strategy.

Outside of his primary role, Darryl is deeply invested in community and industry betterment. He serves as Treasurer and Chair of the Legislative Committee for the Massachusetts Mortgage Bankers Association and is a board member for Food Link MA. In a 2022 interview, he mentioned he grew up idolizing Kobe Bryant and Allen Iverson for their work ethic and determination.

He received a Governors Citation for excellence in national advocacy in 2012.

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Experience
20 Years
Current Role
SVP, Director of Retail Lending & Collections/CRA Officer
Job Level
Leadership
Location
Greater Boston, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Darryl cares about

Mortgage Legislation
As Chair of the Legislative Committee for the Massachusetts Mortgage Bankers Association, he actively analyzes and provides testimony on state legislation impacting the mortgage industry.
Community Development
As CRA Officer at Webster Five, he created a strategic plan to meet the credit needs of low- to moderate-income neighborhoods and serves on a board focused on affordable housing.
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Career

Work history

1-2018
SVP, Director of Retail Lending & Collections/CRA Officer
Webster Five
Board Member/Chair of Legislative Committee
Massachusetts Mortgage Bankers Assoc. (MMBA)
8-2012 - 1-2018
AVP, Associate Counsel
Leader Bank
8-2010 - 8-2012
Legal Clerk/Intern
Law Office of Attorney Peter Kelley
5-2005 - 8-2010
Law Clerk
Troiani Kivitz
In the press

Media appearances

New Director of Retail Lending. Featured in Webster Five (web5.com)
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Caffee named VP/director at Webster Five Cents Savings Bank. Featured in Telegram
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Education
2009 - 2012
Doctor of Law (JD)
Massachusetts School of Law
2005 - 2009
Bachelors of Science
Commonwealth University-Lock Haven
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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