Darryl Caffee

Critic
DISC Type : C

SVP, Director of Retail Lending & Collections/CRA Officer at Webster Five

Greater Boston, United States

Overview

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.

Personality Overview

ROI Driven

Objective Thinker

Negotiator

They like to do things independently and don’t look for support from others.  Unless the value is proven by data, they are unlikely to value fancy features. They choose to analyze logically and value facts to emotions.

Topics They Care 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.
Lending Technology
He has been recognized as a trailblazer for implementing loan origination software to create a more high-tech and efficient mortgage process for clients and borrowers at Webster Five.

Media Appearances

New Director of Retail Lending. Featured in Webster Five (web5.com)

See Now

Caffee named VP/director at Webster Five Cents Savings Bank. Featured in Telegram

See Now

Work History

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

Education

2009 - 2012
Doctor of Law (JD) from Massachusetts School of Law
2005 - 2009
Bachelors of Science from Commonwealth University-Lock Haven

More Information

Social Presence :

Prographics :

Exp : 20 Location : Greater Boston, United States Job Level : Leadership Designation : SVP, Director of Retail Lending & Collections/CRA Officer at Webster Five
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Insights For Selling To Darryl

During A Call Or A Meeting

DO's

  • Tell them what ROI they can expect
  • Leverage facts and figures wherever possible; use percentages, numbers etc.
  • Use phrases like ‘expect X% improvement’, ‘data clearly shows’ etc.

DONT's

  • Don’t rush them till they have clearly gotten all the necessary information
  • Make extra effort to not seem pushy or confrontational
  • Do not use very emotional or colorful language

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Darryl is

  • Proven ROI, pricing and objective proof points are the factors that sway their decision.
  • Will you ever get a clear answer from Darryl

  • They are comfortable saying no if they are convinced that it is the correct decision.

Insights For Deal Planning

    How fast (or slow) will Darryl move?

  • Their decision-making is neither very fast nor very slow, they are somewhere in between.
  • Can Darryl take some risk or not?

  • They can take risks if their analysis shows that it would be worth it.

You And Darryl

Personality Compatibility


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