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A holding company focused on building and operating technology businesses that solve real operational problems for the small and mid-size market. Based in Austin, Texas.
Most organizations skip straight to execution.
The gap isn't capability — it's order of operations.
Look clearly.
Understand where the business is losing time and money before touching any tooling.
Build strategy.
No vendor agenda. No borrowed frameworks. A path specific to how this business makes money and manages risk.
Build only what the strategy calls for.
AI has made the gap between clarity and execution more expensive. We close it in sequence.
Managed IT and cybersecurity services for healthcare organizations. HIPAA-compliant infrastructure, endpoint management, and helpdesk support for medical practices and healthcare-adjacent businesses. Built for organizations where downtime is not an option.
truenorthitg.com → Claude AdoptionClaude adoption consulting for SMB leadership teams. Governance, workspace architecture, repeatable workflows, and training that turn scattered AI use into durable team output. Independent, operator-led, and built around ownership.
lookingglassworks.com → GrowthWebsite development and conversion optimization for businesses that need their digital presence to perform. Focused on turning visitors into qualified leads through deliberate design, automation, and funnel strategy.
calibergrowthagency.com →Founder & CEO, Hokulani Ventures
Jordan Shaw began his career in IT in the late 1990s. In 2005, he co-founded a consulting practice that grew into a $25M Healthcare IT managed services and private EHR hosting company — built by doing, not by advising from a distance.
What he saw repeated across hundreds of client relationships was the same structural gap: growing businesses, real data, and leadership teams who still couldn't answer basic questions about where their operations were losing time and money. Not because the team wasn't capable. Because no one's job was to think about it end to end.
He founded LookingGlass Works to help leadership teams turn scattered Claude use into governed, repeatable work systems: the operating model, workspace structure, workflows, and training needed to make AI adoption durable. No vendor agenda. No borrowed frameworks. No theory that hasn't been tested against a real operation.
Interested in what we're building, or want to explore a working relationship?