Founder + CEO of Gaither Dynamic

About Gaither Stephens, CEO.

A technologist with two decades of operations experience and five years inside a Continuum of Care. Founded Gaither Dynamic in 2019 to put working dashboards in the hands of the people answering the follow-up questions, not just the people who ran the report.

Gaither Stephens

The short version

From the inside of a CoC, then back out.

Gaither has been working with computers since 1984, when he was 9 years old at a university laboratory school. Starting in 1997 he spent eighteen years in radio, hired as Operations Manager and promoted to General Manager within the first year, then Regional Manager across five stations in Cincinnati, Indiana, and Kentucky. Sales, programming, operations, and every piece of the technology stack. That is where the comfort with automation, scale, and "the show has to go on" came from.

From 2016 to 2021 he spent five years inside the homeless response system in Charlotte County, Florida. He started at the Charlotte County Homeless Coalition, the local direct-services provider, as Data Analyst and Systems Administrator. Inside the first year he pulled the community's HMIS data quality from Fs to As. The CoC and HMIS lead functions for Charlotte County (FL-602) were then spun out of the Coalition into a separate organization, Gulf Coast Partnership, to remove the conflict of interest of holding direct services, CoC lead, and HMIS lead under one roof. Gaither moved with them as Chief Technology Officer. Through 2021 he co-built coordinated entry from a blank page with two colleagues, ran the Point-in-Time Count end to end, and owned the LSA, the PIT, and the HIC. Charlotte County reached functional zero for veterans in 2017 and for chronically homeless populations in 2021. He has since returned to the original Coalition as a member of its Board of Directors.

He started Gaither Dynamic in 2019 to do the work nationally. Seven years and 300+ dashboards later, the company still ships every product directly. Same standard he learned on the inside: if the person who needs the answer cannot find it without help, the dashboard is not done.

A career arc

Operations to social services to product.

The throughline is the same in all three: keep the system running, fix what is broken, and make the data legible to the people who depend on it.

  1. 1984

    First lines of code

    Started programming at age 9 at a university laboratory school. Forty-plus years of working with technology, in one form or another, ever since.

  2. 1997 to 2015

    Radio

    Hired as Operations Manager and promoted to General Manager within the first year. Then to Regional Manager across five stations in Cincinnati, Indiana, and Kentucky. Owned operations, sales, programming, and all IT. Eighteen years that built the comfort with automation, scale, and 'the show has to go on.'

  3. 2016 to 2017

    Charlotte County Homeless Coalition

    Joined as Data Analyst and Systems Administrator at the Coalition, the local direct-services provider. Pulled the community's HMIS data quality from Fs to As within the first year.

  4. 2017

    Functional zero, veterans

    Charlotte County reached functional zero for veteran homelessness. A meaningful national milestone, and the result of a lot of careful, quiet work across the system.

  5. 2017 to 2021

    Gulf Coast Partnership, CTO

    The CoC lead and HMIS lead functions for Charlotte County (FL-602) were spun out of the Coalition into a separate organization, Gulf Coast Partnership, to remove the conflict of interest of holding direct services, CoC lead, and HMIS lead under one roof. Gaither moved with them as Chief Technology Officer. Co-built coordinated entry from scratch with two colleagues. Owned the Point-in-Time Count end to end, from media releases to organizing volunteers and police to walk the camps. Tabulated and submitted the LSA, PIT, and HIC every year.

  6. 2019

    Founded Gaither Dynamic

    Started the company to do the work nationally, not just for one CoC. Ran it alongside the CTO role at Gulf Coast Partnership for the first two years, then took it full-time in 2021. Seven years and 300+ dashboards later, the focus has not changed: build dashboards the people who need the answer can actually use, without help.

  7. 2021

    Functional zero, chronically homeless

    Charlotte County reached functional zero for chronic homelessness, a milestone few communities ever reach. Capping the inside work before going full-time on Gaither Dynamic.

  8. 2023 to 2024

    Back to the Coalition, on the board

    Returned to the original Charlotte County Homeless Coalition as a member of its Board of Directors. Full circle: data analyst to governance, with everything in between.

Beyond dashboards

What Gaither actually does for communities.

Gaither Dynamic is more than a dashboard shop. The full picture of how the company helps Continuums of Care, agencies, and local governments do the work.

Custom dashboards

HMIS-powered dashboards for Continuums of Care, agencies, and local governments. APR, HDX 2.0, hashed HUD CSV. HUD 2026 Data Standards compatible.

Consulting

One-on-one work on data quality, HMIS administration, system performance measures, and reporting strategy.

Coordinated Entry

Help communities design or rebuild their CE processes. Drawn from launching a CE system from a blank page.

HMIS cleanups

Diagnose what is broken, fix it, document it. The kind of multi-month grind most communities cannot spare staff to run.

Speaking

Frequent presenter at HSTC, NHSDC, FCEH, NAEH, and other national and regional convenings on data, AI in social services, and system performance.

Writing

Regular Substack articles on housing policy, measurement, and the practical edges of CoC work, plus a monthly homelessness newsletter delivered to inboxes across the field.

Education

Engineering, business, math, philosophy.

Three degrees across two decades. The blend shows up in the product: the math and engineering decide what the dashboard calculates, the business and philosophy decide how it talks to the person reading it.

  • Master of Science, Computer Information Systems

    Boston University

    Concentrations in Database Management and Business Intelligence

  • Bachelor of Business Administration

    Indiana Wesleyan University

    Graduated cum laude

  • Associate of Science, Computer Science and Information Systems

    Purdue University

    Double major: Mathematics and Philosophy

Outside the company

Speaking, writing, and CoC Alliance.

Gaither presents nationally and regionally on data quality, system performance measures, and the role AI is starting to play in social services. He also founded CoC Alliance, a free resource hub uniting Continuums of Care around the work of making homelessness rare and brief, and writes regularly on Substack about housing policy, measurement, and the practical edges of CoC work.

Want to talk?

A full hour, no deck, no sales pressure. Tell me what your community is trying to figure out and I will tell you the shortest path to seeing it in a dashboard.