About Association Pilot

Domain-led AI consulting for HOAs and community association management companies.

Donald F. Rogers, founder of Association Pilot
Founder

Donald F. Rogers, CMCA

Most AI tools built for HOAs are built by people who have never read a CC&R.

I've spent my career on the other side of that gap — managing 13 community associations and 2,000+ homes, running board meetings, enforcing governing documents, and handling the architectural review packets, compliance letters, and resident questions that fill a manager's day. That work earned Rookie of the Year honors, two promotions in two years, and a 75% reduction in compliance issues across my portfolio.

Now I build AI agents that do that intake work the way governing documents actually require.

I'm the founder of Community Concierge, an AI-powered resident support assistant for HOA communities. Our first production agent automates architectural application intake end to end: document completeness checks, neighbor signature validation, deficiency notices, and committee review-deadline tracking — the process most likely to expose an association to selective-enforcement claims, made consistent and defensible.

The difference is domain-led design. I know where ARC intake breaks down, which deadlines carry legal weight, and what boards actually need to see — because I've lived it, not researched it. That's the standard I believe AI for community associations should meet.

Credentials & Scale

  • CMCA Certified Manager
  • 13 associations managed
  • 2,000+ units overseen
  • $5M+ operating budgets managed
  • $325K capital project delivered on budget & schedule
  • 75% reduction in compliance issues

If you're weighing AI for resident support or architectural review…

…or wondering whether the tools you're being pitched actually understand your governing documents, let's talk.

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