Jillyn Dillon in

Jillyn Dillon

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Founder & Chief Strategy Officer at Technology Aloha
📍 Maui, United States

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.

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Experience
18 Years
Current Role
Founder & Chief Strategy Officer
Job Level
Leadership
Location
Maui, United States
Personality Overview

How Jillyn shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Jillyn cares 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.
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Career

Work history

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

Media appearances

Jillyn Dillon, Founder — Technology Aloha. Featured in HandsOn Maui
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Education
2007 - 2008
MS Coursework
Naval Postgraduate School
2004 - 2005
MBA
The University of Southern Mississippi
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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