Ryan Weber

Trailblazer
DISC Type : DI

Director of Sales Enablement at City Wide Facility Solutions

Kansas City Metropolitan Area, United States

Overview

Ryan is a seasoned operations executive with over 20 years of experience managing multi-billion-dollar retail environments. As the Director of Sales Enablement at City Wide Facility Solutions, he focuses on enterprise workforce strategy and P&L management. People who have worked with him describe him as an outstanding leader adept at building and empowering teams.

He directed a $1B labor portfolio at H&R Block, overseeing a workforce of over 70, 000 associates across 6, 500 locations.

Personality Overview

Persuasive

Achievement-Oriented

Informal

They will bat for you if they come to believe in you.  They are more likely to be open to unproven but exciting technologies. They like to keep things under control.

Topics They Care About

Sales Enablement
In his current role as Director of Sales Enablement, he is actively building out his team to drive growth and operational excellence.
Large-Scale Operations
He has extensive experience translating high-level strategy into scalable operational models for workforces as large as 70, 000 associates across 6, 500+ locations.
Talent Development
His social media posts and recommendations highlight a passion for coaching performance, developing talent, and building teams that win.

Media Appearances

Ryan has no verified media appearances

Work History

1-2026
Director of Sales Enablement at City Wide Facility Solutions
12-2020 - 6-2025
Vice President of Tax Professional Experience at H&R Block
12-2019 - 1-2020
Tax Professional Experience Project Manager at H&R Block
6-2015 - 1-2020
Regional Director of Sales and Service at H&R Block
1-2011 - 6-2015
District Manager (Charlottesville, VA) at H&R Block

Education

1999 - 2003
Bachelor of Business Administration (B.B.A.) from St. Bonaventure University

More Information

Social Presence :

Prographics :

Exp : 20 Location : Kansas City Metropolitan Area, United States Job Level : Mid-senior Designation : Director of Sales Enablement at City Wide Facility Solutions
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Address your competition clearly and confidently
  • Ask them for a lunch or coffee once some rapport has been established
  • Help them visualize the impact of their decision

DONT's

  • Don’t force involvement of other stakeholders unless it is critical
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Do not look like someone who doesn’t know what they are talking about

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Ryan

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Ryan take some risk or not?

  • They can take risks if necessary.

You And Ryan

Personality Compatibility


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