Chicagoland · Built for small & mid-sized business
Custom applications, secure knowledge systems, revenue workflows, and fractional AI leadership—from a builder with 25 years of enterprise operating experience.
No AI theater. One costly workflow, a controlled pilot, and proof before scale.
SERVICE CATALOG
Every engagement starts with a narrow business problem, explicit boundaries, and a way to measure whether the system earned the right to expand.
Find customers who stopped coming back, estimate recoverable revenue, and launch human-approved win-back campaigns.
A voice-first assistant that answers routine questions, captures intent, supports booking, and knows when a human needs to step in.
Turn discovery notes into a grounded proposal, buyer-ready experience, contract handoff, and measurable follow-through.
Give each team or customer a private, cited assistant over the documents they are actually allowed to see.
Convert dense internal material into branded playbooks, guides, diagrams, and searchable working knowledge.
Replace a brittle spreadsheet, inbox chain, or disconnected process with one secure application built around the real workflow.
A practical review of where AI can save time, where it creates risk, and what should be built first—or not built at all.
Senior AI leadership that can set direction, govern vendors, and stay close enough to the work to ship production systems.
Put explicit boundaries around what an agent may do, what requires approval, and how the business can stop it safely.
RESEARCH-LED MARKET FOCUS
The next focused offer is a customer reactivation engine for med spas and recurring-service businesses: audit the list, identify who is winnable, launch approved outreach, and attribute recovered revenue. The promise is commercial—not “AI-powered.”
SELECTED BUILT SYSTEMS
The catalog is backed by real applications, repositories, database designs, migrations, deployment workflows, and operating lessons.
A secure proposal workspace designed to move from discovery notes to buyer-ready proposal, client context, and measurable follow-through.
A private document transformation and retrieval system that turns working material into organized, searchable knowledge with semantic retrieval, citations, and authenticated access.
A containerized foundation joining voice, SMS, chat, admin controls, client dashboards, PostgreSQL, and Redis for practical small-business workflows.
THE BOOTS STANDARD
Good AI is not a clever demo. It is a controlled operating system with owners, permissions, evidence, fallbacks, and a clean way to stop.
Map the workflow, failure cost, data, and success metric before choosing a model.
High-impact actions get approval gates, escalation paths, and accountable owners.
Role-based access and row-level security are architecture, not a launch-week patch.
Logs, usage, spend, quality checks, and audit history make failure diagnosable.
Models are selected per task and cost profile; the business is not trapped by hype.
Documentation, runbooks, rollback paths, and ownership are part of the deliverable.
PROOF IN PRODUCT
Real interfaces from Boots-built applications: multi-agent business onboarding, conversational intake, and notes-to-proposal generation.
HOW AN ENGAGEMENT WORKS
The safest path for a small business is deliberately boring: validate one expensive problem, ship in phases, and fund expansion with evidence—not optimism.
Current state, data, users, authority, risk, and one measurable outcome.
Small scope, human review, clear timebox, and real operating data.
Security, integrations, monitoring, documentation, and failure recovery.
Scale across locations, teams, or channels when the numbers support it.
ABOUT THE BUILDER
Boots On The Ground AI is led by Damara Carlentine, a production-minded AI founder with 25 years in technology and operations—including leading conversational AI work at McDonald's scale.
The difference is practical: she can sell the pain, design the system, build the product, document the proof, and govern the risk. The learning has not stopped; the work continues roughly 60 hours every week.
View the professional profile ↗START WITH THE WORK
We will determine whether it needs AI, ordinary software, process repair, or no build at all. That answer is more valuable than another demo.