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The AI team at IT Hawaii

ITHawaii.AI is where IT Hawaii puts its AI work. We help Hawaii businesses get their teams working with AI, build AI agents that finish routine tasks, and keep their data safe while they do it.

  • Since 2001
  • A team of 15
  • Honolulu and Lihue
Book a discovery call Call 808.468.4245
Kai, the ITHawaii.AI robot, wearing a lei and giving a shaka above the Na Pali coast on Kauai

From a home office on Kauai to AI agents statewide

Mark Gregory started IT Hawaii in his home on Kauai in 2001, after hearing about all the tech support trouble on the island.

Steve Massaro partnered with him in 2007, and together they grew it from 3 people to 15. Today IT Hawaii runs its own business on TruerunEngine, the AI agent platform it built, and ITHawaii.AI brings those tools to Hawaii businesses.

An illustration of a small home office on Kauai with green mountains in the window and a laptop showing the Hawaiian islands linked together
Since 2001Supporting Hawaii businesses
15People on the IT Hawaii team
2Offices, in Honolulu and Lihue
StatewideAI services on every island

Built by people who know how AI works

Our Hawaii-based team includes computer scientists, an AI specialist with a master’s degree and a data scientist.
  • The AI we build for you is designed by people who understand it inside and out
  • Team members also hold Security+, Network+ and AWS certifications
  • IT Hawaii is a certified partner of Microsoft
Kai, the ITHawaii.AI robot, explaining a neural network diagram on a whiteboard to three colleagues

Meet the AI team you'll work with

  • An illustration of Steve Massaro

    Steve Massaro

    CEO

  • An illustration of Aitor Elfau

    Aitor Elfau

    Senior AI Architect

  • An illustration of Josh Cohen

    Josh Cohen

    AI Adoption Specialist

  • An illustration of Sarah Thayer

    Sarah Thayer

    AI Adoption Specialist

The values behind every project

IT Hawaii’s four values guide our AI work too.

Service with Aloha

We treat your team the way we’d want ours treated, with warmth and patience.

Technology protection

Your data comes first, from the AI provider contract to the access each agent gets.

Responsiveness

A real person will reach out within one business day.

Experience and trustworthiness

Supporting Hawaii businesses since 2001, and honest about fit. If another builder suits you better, we’ll say so.

Say aloha to Kai

Kai is the ITHawaii.AI mascot, a friendly robot who shows up wherever we talk about AI.
  • Kai means sea in Hawaiian. We’re riding the AI wave, and Kai is here to bring your team along for the ride.
  • His shell is a honu, the Hawaiian green sea turtle, at home in the same waters.
  • He wears headphones because good help starts with listening.

Kai can’t take your call yet. Our team can, at 808.468.4245.

You'll find Kai across our services.

An illustration of Kai, the ITHawaii.AI robot, jumping for joy on a Hawaii coastal highway between green mountains and the ocean

Questions we hear a lot

Who is behind ITHawaii.AI?
ITHawaii.AI is the AI team at IT Hawaii (IT Kauai, Inc., dba ITHawaii.com), which has supported Hawaii businesses since 2001. The team includes computer scientists, an AI specialist with a master’s degree and a data scientist.
Where are you located?
IT Hawaii has offices in Honolulu (1003 Bishop St., Ste. 2160) and Lihue (4370 Kukui Grove St., Ste. 3-111). ITHawaii.AI’s services are offered statewide, and training runs remotely.
Is ITHawaii.AI a separate company from IT Hawaii?
ITHawaii.AI is part of ITHawaii.com. It has its own name and website for AI, and the same IT Hawaii team stands behind it.

Ready to see what AI can do for your team?

Tell us where your team spends its time, and we'll show you where AI can give some of it back.

A real person will reach out within one business day.

Book a discovery call 808.468.4245