Winston S. Williams MBA, ChFC®, CLU®,CIAM, PMP®, MFA, RFC®

Questioner
DISC Type : c

Chief Executive Officer for the Caribbean at Pan-American Life Insurance Group

San Fernando, San Fernando, Trinidad and Tobago

Overview

Winston S. Williams is the Chief Executive Officer for the Caribbean at Pan-American Life Insurance Group, bringing over four decades of experience. An alumnus of The American College, he specializes in business succession, retirement planning, and developing elite sales teams, with a proven record of driving consecutive years of growth.

His passion for the insurance industry is rooted in a desire to help people, focusing on mentoring professionals and fostering leadership. He is deeply involved with GAMA Global, an organization dedicated to elevating the financial services profession and shaping managers into visionary leaders, reflecting his commitment to industry-wide excellence and collaboration.

He has been inducted into the Hall of Fame in recognition of his significant contributions to the insurance industry.

Personality Overview

Cautious & Analytical

Systematic

Value Seeker

They are more likely than others to negotiate on pricing and terms.  They prefer to fully evaluate every situation. While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters.

Topics They Care About

Leadership Development
He is passionate about transforming managers into visionaries and elevating the financial services profession, as shown by his involvement and posts about GAMA Global.
Client-First Approach
He advocates for integrity and putting the client first, a principle reflected in his professional posts and personal recommendations that praise his detailed, client-centric methods.
Financial Legacy
He emphasizes helping families achieve long-term financial goals and building lasting relationships across generations, viewing it as a core commitment.

Media Appearances

Winston has no verified media appearances

Work History

11-2025
Chief Executive Officer for the Caribbean at Pan-American Life Insurance Group
7-2013 - 11-2025
Agency Manager at Pan-American Life Insurance Group
9-1999
Chairman & C.E.O. at Financial Advisory Services Ltd
4-1999 - 11-2025
Chairman and CEO at Financial Advisory Services Limited
10-2009 - 6-2013
Vice President of Sales and Marketing at Sagicor Life Insurance Company

Education

5-2018 - 2021
Chartered Financial Consultant ChFC® from The American College of Financial Services
3-2008 - 3-2011
Chartered Insurance Agency Manager from Life Insurance Management Research Association

More Information

Social Presence :

Prographics :

Exp : 26 Location : San Fernando, San Fernando, Trinidad and Tobago Job Level : Leadership Designation : Chief Executive Officer for the Caribbean at Pan-American Life Insurance Group
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Insights For Selling To Winston S.

During A Call Or A Meeting

DO's

  • Emphasise more on facts and measurable benefits
  • Tell them that you will come back if you don’t have a good answer for a question
  • Back up any claims with data and numbers

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Avoid rushing them, be polite and patient
  • Don’t depend too much on anecdotal evidence, it reduces their confidence

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Winston S. is

  • Confidence that the product provides ROI, effective pricing and process adherence matter the most to them.

  • Will you ever get a clear answer from Winston S.

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Winston S. move?

  • They can move at a reasonable pace while making their decisions if they have the necessary information.

  • Can Winston S. take some risk or not?

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Winston S.

Personality Compatibility


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