Jillyn Dillon

Activist
DISC Type : Cd

Founder & Chief Strategy Officer at Technology Aloha

Maui, United States

Overview

Jillyn Dillon is a Fractional Chief Strategy Officer and the founder of Technology Aloha, where she advises leadership on growth, market positioning, and AI-driven business models. Drawing on experience from Northrop Grumman and an MBA, people who have worked with her describe her as strategic, expert, and an outstanding professional.

Outside of her strategic work, Jillyn is an avid enthusiast of complex board games, purchasing custom organizers for titles like "Brass: Birmingham" and "Terraforming Mars" to enhance gameplay and setup efficiency. She also has a hands-on interest in DIY electronics, having once built a replacement for Boses cloud infrastructure for her speaker.

Unique fact: She uses AI informed by personality models like DiSC to tailor her own emails to the recipients communication style, improving understanding and reducing friction.

Personality Overview

Perfectionist

Observative

Logical And Quick

They care equally about the product and its potential impact.  They don’t always try to control the conversation but neither do they like yielding it fully. They can be nudged to make faster decisions by offering what they value.

Topics They Care About

Emotionally Intelligent AI
Was recently featured in a Forbes article discussing the complexities of integrating emotional intelligence and behavioral models like DiSC into AI to enhance human communication.
Strategic Board Games
Actively purchases and reviews custom organizers and components for complex board games like "Brass: Birmingham" and "Terraforming Mars, " indicating a strong personal hobby.
Growth & Positioning
Her entire career, from Northrop Grumman to founding Technology Aloha, is focused on competitive intelligence, brand development, and creating actionable growth strategies for businesses.

Media Appearances

Jillyn Dillon, Founder — Technology Aloha. Featured in HandsOn Maui

See Now

Work History

10-2012
Founder & Chief Strategy Officer at Technology Aloha
8-2009 - 12-2011
Sr. International Business Development Specialist at Northrop Grumman
10-2008 - 7-2009
Sr. Competitive Intelligence Analyst at Northrop Grumman
9-2007 - 9-2008
Sr. Systems Engineer at Northrop Grumman
11-2001 - 10-2002
Configuration Analyst at CDI Marine Co

Education

2007 - 2008
MS Coursework from Naval Postgraduate School
2004 - 2005
MBA from The University of Southern Mississippi

More Information

Social Presence :

Prographics :

Exp : 18 Location : Maui, United States Job Level : Leadership Designation : Founder & Chief Strategy Officer at Technology Aloha
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Insights For Selling To Jillyn

During A Call Or A Meeting

DO's

  • Tell them that you are there to help them create visible impact within their organization
  • Ask them questions confidently while doing discovery, don’t be apologetic
  • Refer to testimonials from others in similar positions

DONT's

  • Avoid long winding pitches, stay objective
  • Don’t expect them to change their mind quickly if they say no once
  • Do not give up if they are not convinced, try again with a different approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jillyn is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Jillyn

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Jillyn move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Jillyn take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Jillyn

Personality Compatibility


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