Stephanie Medaglia

Examiner
DISC Type : cs

Manager, Financial Wellbeing & Retirement at Paychex

Greater Tampa Bay Area, United States

Overview

Stephanie Medaglia is the Manager of Financial Wellbeing & Retirement at Paychex, bringing over 20 years of experience in human resources. Her expertise spans employee benefits, retirement plans, and HRIS. She holds a Bachelor of Arts degree and studied Business Administration and Management at Immaculata University.

Stephanie is a strong advocate for positive workplace culture. She believes that for companies to succeed, it is essential that employees feel valued and respected, a sentiment she has publicly endorsed.

She is HIPAA Certified, underscoring her proficiency in managing sensitive employee health information and compliance.

Personality Overview

Late Adopter

Process Oriented

Overcautious

They do not like taking risks at all and go for proven options in the end.  Being observant comes to them naturally. The only way to convince them is by showing them examples and ample proof.

Topics They Care About

Employee Wellbeing
Her current role focuses on financial wellbeing, and she publicly advocates for ensuring employees feel valued and respected in the workplace.
Retirement Planning
A core part of her current and past roles, with deep experience in 401(k)s, qualified plans, and non-qualified deferred compensation.
Benefits Administration
Has over eight years of hands-on experience in managing and administering health & welfare benefits for large corporations.

Media Appearances

Stephanie has no verified media appearances

Work History

9-2025
Manager, Financial Wellbeing & Retirement at Paychex
9-2018 - 3-2025
Senior Manager, US & PR Benefits & Retirement Plans at Bristol Myers Squibb
6-2012 - 7-2018
Manager - Data Management Department at Benefit Harbor

Education

2001 - 2002
Business Administration and Management from Immaculata University
2019 - 2021
Bachelor of Arts - BA from Ashford University

More Information

Social Presence :

Prographics :

Exp : 13 Location : Greater Tampa Bay Area, United States Job Level : Middle Designation : Manager, Financial Wellbeing & Retirement at Paychex
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Insights For Selling To Stephanie

During A Call Or A Meeting

DO's

  • Be firm in your communication and stay in control
  • Spend time addressing concerns around risk and change, they will have them even if they don't express them
  • Expect them to be vague in response to your questions, ask firmly and pointedly

DONT's

  • Avoid getting into storytelling mode, especially when they ask specific questions
  • Don't push them too hard to make fast decisions, give them time
  • Don't use phrases like 'do not worry', 'i promise' etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephanie is

  • Low-risk, adoption by others are very important to them, followed by confidence in ROI.
  • Will you ever get a clear answer from Stephanie

  • Often, they don't say no, or keep going about it in circles.

Insights For Deal Planning

    How fast (or slow) will Stephanie move?

  • They do not like to rush and therefore can be quite slow in their decision-making.
  • Can Stephanie take some risk or not?

  • They have little risk-appetite and prefer to take measured decisions.

You And Stephanie

Personality Compatibility


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