Keston Glasgow
AI ENABLEMENT + TRANSFORMATION

AI transformation fails at the human layer.

I've spent over a decade on both sides of that line.

I protected systems from external threats.

Then I learned the threats that live inside people.

Now I build AI that works because humans actually use it.

8 YEARS WALL STREET CYBERSECURITY · CERTIFIED HIGH PERFORMANCE COACH · LIVE APP STORE AI PRODUCT · 5+ CORPORATE AI WORKSHOPS DELIVERED

SHIPPED, NOT SLIDES

Systems I have built and run.

SHIPPED PRODUCT, LIVE IN THE APP STORE

MIO Connect

A behavioral intelligence platform for couples I built end to end and operate in production. Three-stage RAG pipeline over 8,000+ embedded research chunks, 33 behavioral analysis capabilities, voice AI, and production eval gates. Product, backend, payments, iOS pipeline, and deploys: all mine.

Claude + OpenAI · RAG / vector embeddings · Supabase / Postgres / RLS · Stripe · iOS + web · Cloudflare

AUTONOMOUS AGENT FLEET

Agent OS

A fleet of autonomous AI agents running 24/7 on VPS infrastructure for my own businesses. Research, content drafting, scheduled jobs, and a chat command center, with multi-model orchestration across providers.

Multi-agent orchestration · VPS / Docker · Cron + webhooks · Telegram ops

CLIENT SYSTEM, BUILT AND OPERATED

Production support agent

An AI support and coaching agent answering real customers inside a client's education platform. I built it, deployed it, and operate it like an SRE: root-causing outages, fixing timeout chains, and resolving tickets when it breaks. Building agents is easy. Running them in production is the skill.

n8n workflows · Claude · Cloudflare Pages · Supabase · Incident response

CLIENT SYSTEM, MEASURED ROI

Appraisal automation agents

A two-agent system for a real estate appraisal firm: one agent scrapes county, MLS, and tax sources in parallel; a second QC agent reviews every field against source data. Cut the owner's review time by roughly half and opened a clear path to doubling monthly capacity.

Parallel scraping agents · QC / validation agent · Structured output

CLIENT SYSTEM, CONFIDENTIAL

Performance audit platform

For a senior performance executive at a world-class sports organization: the AI transformation of a comprehensive high performance audit instrument, from a manual workbook into a scalable platform design with benchmarking and trend analysis.

AI product architecture · Assessment analytics · Executive advisory

GENERATIVE PRODUCTION SYSTEM

AI media pipeline

A complete AI spokesperson system for a coach: cloned voice, an approved stylized avatar built from real photos, and lip-synced video generation. Five-minute videos at a small fraction of filming cost, with a proven per-video cost model.

Voice cloning · Image + video generation · Lip sync · Cost engineering

THE HUMAN LAYER

The half of AI transformation that engineering can't solve.

Every AI initiative dies the same way: the tools work and the people don't change. Adoption is a behavior problem. That is the problem I trained for.

5+ corporate AI workshops delivered

Executive and team sessions on what agentic AI actually means in practice. Not prompts. Systems that act on your behalf, and what it takes for a team to trust them.

Certified High Performance Coach

Certified in high performance coaching and relational intelligence. Years of coaching operators and couples through the hardest behavior changes there are.

Adoption built into my own products

Onboarding flows, retention loops, and habit design inside products I run. I don't theorize about adoption curves. I watch mine every week and tune them.

WHY ME

Same architecture, different domain.

I spent 8 years in Wall Street cybersecurity, working up from help desk to security engineer at a law firm. Threat detection, incident response, compliance. My job was protecting systems from external threats.

I left to build my own businesses and built a $10M real estate portfolio. Then I got certified in high performance coaching and spent years coaching entrepreneurs and couples. That work taught me the other threat model: the internal patterns that make smart people resist the very change they asked for.

When agentic AI arrived, my two careers turned out to be one career. Threat detection became pattern detection. Incident response became intervention design. Compliance became daily practice. Same architecture, different domain.

So I built. A live App Store product with a full RAG pipeline. Agent fleets that run my businesses while I sleep. Client systems I operate in production, including the 2am debugging. And workshops that turn skeptical teams into adopters.

That combination is the job description of AI transformation. Most builders can't drive adoption. Most adoption people can't build. I do both, and I have the shipped systems to prove it.

CAPABILITIES

What I do for organizations.

AI strategy + roadmaps

Use-case discovery, build-vs-buy calls, and a sequenced roadmap tied to business outcomes, not demos.

Agentic systems + RAG

Production agent design, retrieval pipelines, vector search, evals, and the guardrails that keep them honest.

Workflow + automation design

Mapping real processes into automations people keep using. n8n, APIs, and the glue between systems.

AI fluency training + workshops

Executive sessions and hands-on team training that move people from anxious to fluent.

Adoption + change programs

Behavior-change design for rollouts: champions, habit loops, and the metrics that show real usage.

Governance + security

Eight years of enterprise security instincts applied to AI: data boundaries, access, risk, and compliance posture.

WORK WITH ME

Bring this to your organization.

Whether you need a fractional AI lead, a transformation partner, or a builder who can also win over your team, the first step is a conversation.