Robert Darrow, CFP®

Questioner
DISC Type : c

President, Co-Founder at Strive Retirement Group

Lake Mary, Florida, United States

Overview

Robert is an acquisition entrepreneur and CERTIFIED FINANCIAL PLANNER™ specializing in the retirement industry. As Co-Founder of Strive Retirement Group, he focuses on corporate retirement plans, leveraging his experience from roles like CRO at Excel Wealth Management and National Sales Manager at Paychex.

He has a strong interest in how technology, particularly AI, is transforming productivity. Robert is also passionate about mentoring the next generation of financial advisors and has an appreciation for the sport of distance running and its pioneers.

Unique fact: He recently attended a university conference to connect finance majors with advisory firms for internships, showing his commitment to nurturing new talent.

Personality Overview

Price-Sensitive

Not Easily Convinced

Systematic

They generally do not appreciate an overfriendly approach and prefer to stay to-the-point.  They prefer to fully evaluate every situation. They are more likely than others to negotiate on pricing and terms.

Topics They Care About

Corporate Retirement
As the co-founder of a firm that focuses on corporate retirement plans, this is his core professional expertise and business focus.
AI & Productivity
He has recently shared thoughts on how artificial intelligence is beginning to transform productivity and our perception of reality.
Mentoring Students
He recently attended a conference at the University of Florida specifically to connect finance majors with advisory firms for internships.

Media Appearances

Robert Darrow of Strive Retirement Group in Lake Mary, FL. Featured in Vimeo

See Now

Work History

2-2025
President, Co-Founder at Strive Retirement Group
5-2022 - 2-2025
Chief Revenue Officer (CRO) at Excel Wealth Management, LLC
7-2021 - 5-2022
Retirement Plan Recordkeeping and HCM Consultant - Contract Work at Independent Contractor
3-2014 - 6-2021
National Sales Manager - 401(k) Wholesale Division at Paychex
7-2009 - 3-2014
Regional Sales Director - Major Markets Southeast at Paychex

Education

1984 - 1988
Bachelors from University of South Carolina

More Information

Social Presence :

Prographics :

Exp : 36 Location : Lake Mary, Florida, United States Job Level : Leadership Designation : President, Co-Founder at Strive Retirement Group
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Insights For Selling To Robert

During A Call Or A Meeting

DO's

  • Share as much information as possible regarding your product
  • Tell them that you will come back if you don’t have a good answer for a question
  • Emphasise more on facts and measurable benefits

DONT's

  • Don’t try to be too friendly or informal with them
  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.
  • Avoid rushing them, be polite and patient

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Robert 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 Robert

  • 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 Robert move?

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

  • Can Robert take some risk or not?

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

You And Robert

Personality Compatibility


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