Rory Cooksey

Trailblazer
DISC Type : DI

Vice President of Brand & Business Development at WheelHouse IT

Fort Lauderdale, Florida, United States

Overview

Rory Cooksey is the VP of Brand & Business Development at WheelHouse IT, where he merges technical services with compelling brand narratives to drive growth. He has over a decade of experience leading marketing, sales, and strategy teams. Recommendations frequently describe him as innovative, creative, and a great community leader.

Outside of work, Rory is deeply involved in his South Florida community, volunteering for organizations like the FLITE Center and Ronald McDonald House Charities. He previously co-hosted a consumer technology radio show and worked in entertainment for Carnival Cruise Line. His posts suggest he enjoys boating on the New River.

He has a passion for community engagement and was a presenter at the Visit Lauderdale Food & Wine Festival.

Personality Overview

Informal

Values Relationships

Achievement-Oriented

They will fight for you if they come to believe in you.  A combination of speed and relationship gets the best response from them. They are more likely to accept new and exciting technologies.

Topics They Care About

Brand Storytelling
His professional focus is on bridging the gap between technical services and compelling narratives to drive business growth.
IT for Law Firms
Recently appeared on a podcast discussing how law firms can use technology, cybersecurity, and AI as a strategic investment for growth.
Community Fundraising
He is active in community engagement, serving as Vice President for the 'Undercover Santa' charity and participating in fundraising events like 'Men of Style'.

Media Appearances

Scale Faster With This Law Firm IT Strategy – Podcast featuring Rory Cooksey (VP, Brand & Business Development, WheelHouse IT). Featured in Law Firm Marketing Pros

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Work History

5-2025
Vice President of Brand & Business Development at WheelHouse IT
7-2020 - 5-2025
Director of Growth at WheelHouse IT
7-2016 - 5-2025
Manager of Business & Brand Development at WheelHouse IT
4-2016 - 7-2016
Radio Co Host at Into Tomorrow with Dave Graveline (Consumer Tech News)
4-2015 - 4-2016
Vice President at The Florida Scholastic Press Association

Education

Human Resources Management and Services from Florida Atlantic University
Business Administration and Management from Broward College

More Information

Social Presence :

Prographics :

Exp : 21 Location : Fort Lauderdale, Florida, United States Job Level : Senior Designation : Vice President of Brand & Business Development at WheelHouse IT
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Insights For Selling To Rory

During A Call Or A Meeting

DO's

  • Address your competition clearly and confidently
  • Give them control of the sales process
  • Talk about yourself and some of your achievements at the start of the conversation

DONT's

  • Don’t force involvement of other stakeholders unless it is critical
  • Don't make any commitments that you might not be able to fulfill
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Rory is

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

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Rory move?

  • They can reach decisions quickly if they develop trust and confidence in the product.
  • Can Rory take some risk or not?

  • If necessary, they will be ready to take risks.

You And Rory

Personality Compatibility


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