Barry Flanagan

Visionary
DISC Type : Ds

CEO\Founder at AI-IQ Systems

Granger, Indiana, United States

Overview

Barry Flanagan is the CEO and Founder of AI-IQ Systems, specializing in AI-powered SaaS solutions for B2B tech sales. With extensive experience at VMware and Citrix, he has a proven track record of scaling revenue from \$2M to \$50M ARR. He studied Economics at the University of North Florida.

Colleagues and direct reports consistently describe Barry as a dynamic, visionary, and strategic leader. He is recognized for his deep expertise in Go-to-Market strategy and his ability to mentor and elevate his team members, fostering significant career growth and achieving remarkable results.

Unique fact: Barry was one of the original Citrix Systems Engineers in the late 1990s, teaching the principles of End-User Computing technology from its early days.

Personality Overview

Objective Evaluator

Early Adopter

Risk Tolerant

They are very professional in their approach and can weigh multiple perspectives together.  They might take some time to make their mind up but once they do, they don't change it easily. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care About

AI in Sales
His current company, AI-IQ Systems, is dedicated to building AI-powered SaaS tools specifically to accelerate B2B technology sales cycles and improve buyer intelligence.
B2B Go-to-Market
He has a history of transforming GTM strategy, having reversed five years of decline at eG Innovations and scaled sales teams and revenue significantly at ControlUp.
Sales Psychology
He actively posts about the psychological signals in sales, referencing thought leaders like Robert Cialdini to understand what motivates buyer decisions beyond the product offer.

Media Appearances

Barry has no verified media appearances

Work History

1-2026
CEO\Founder at AI-IQ Systems
12-2024 - 12-2025
Vice President, Americas Sales at eG Innovations
4-2018 - 10-2024
VP, Americas & APAC Sales | Digital Employee Experience | DEX | Monitoring | EUC at ControlUp
7-2016 - 3-2018
Director, EUC Partner Practice Recruitment | Desktop Virtualization | Digital Employee Experience at VMware
11-2014 - 7-2016
Vice President, WW Sales & Marketing | Citrix | VMware| Digital Employee Experience| BYOD at hopTo

Education

Education details unavailable from University of Florida
Economics from University of North Florida - College of Business Administration

More Information

Social Presence :

Prographics :

Exp : 25 Location : Granger, Indiana, United States Job Level : N/A Designation : CEO\Founder at AI-IQ Systems
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Insights For Selling To Barry

During A Call Or A Meeting

DO's

  • Suggest clear next steps with confidence, don't be vague or hesitant
  • Come across as a trustworthy professional and be respectful, they usually know their game
  • During followups, use phone or text if needed, they should be fine

DONT's

  • Avoid putting conscious effort into relationship-building
  • Don't take their patience for granted, avoid long-winding sermons
  • Don't shy away from asking hard questions, but be extra polite

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Barry is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Barry

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Barry move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Barry take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Barry

Personality Compatibility


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