Born Ready for American-AI to "Build, Baby, Build" with evidence.
Boots stands ready to architect "America AI" driving economic competitiveness, protecting America data security, and ensuring that every worker, business, and community becomes fully AI-ready.
a SAM.gov registered, Women-Owned Small Business (WOSB) certified software development firm
Zero-trust, secure-by-design AI compliant systems.
Fully functional, production-grade software already architected, deployed, and audited under strict zero-trust engineering standards.
Start with the work
you need to improve.
Choose a focused engagement or connect several capabilities into one system. Every service starts with your workflow, your data, and a clear definition of done.
Pilot low-risk "try-first" deployments.
Overcome institutional adoption barriers.
We deploy multi-provider data infrastructure that eliminates data exposure and technical adoption friction for local entities.
Build your own open-weight AI model
Responsible AI with self-indexing knowledge engines
Total data isolation for entities with sensitive data unable to use public closed APIs.
Software Consulting
Make the next technology decision with a clear plan.
Assess your workflows, existing systems, data, and AI risks. Get a practical implementation roadmap tied to business priorities and operating constraints.
Procurement Toolbox Catalogs
Build the missing piece of your operation.
Create custom AI agents, automations, integrations, and operational tools that connect the systems your business already uses.
AI Governance & Safety Controls
Give automation a clear operating boundary.
Build policy checks, approval queues, activity logs, escalation paths, and stop controls around consequential AI actions.
AI Center Of Excellence
Find an answer. See where it came from.
Turn approved documents and business knowledge into a searchable assistant with source citations, access controls, and a defined path for unanswered questions.
Bilingual Wokforce Voice Assistants
Mobile-first, org-scoped voice assistants.
Build voice workflows for questions, lead intake, scheduling, and service requests, with business-specific rules and a clear handoff to a person.
AI Proposal-to-Cash Automation
Move from discovery to a clear next step.
Connect buyer research, proposals, contracts, approvals, payment steps, and onboarding in a workflow scoped to your business. Keep review at the decisions that matter.
Built for local businesses and growing organizations. Scope, integrations, acceptance criteria, and ongoing support are defined before implementation.
The work behind
the services.
Boots products are independently built and deployed projects. Explore the work or request a walkthrough of the capabilities relevant to your business.
Boots Proposals
Buyer research and proposal workflows built around source visibility and human review.
Explore Boots Proposals ↗Boots Command Center
A workspace for organizing projects, agents, skills, notes, and business assets.
Request a Command Center walkthrough ↗Boots Proposal Portal
A document hub for organizing proposal materials and reusable business content.
Request a Portal walkthrough ↗These are Boots-owned portfolio projects. Client implementations are separately scoped and reviewed for current functionality, security, integration needs, and maintenance.
From business problem
to controlled operation.
The build is part of the engagement. So are the operating rules, failure paths, and decisions about who owns the system after launch.
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01 / DISCOVER
Find the constraint.
Map the actual work, the people involved, the data, and the outcome worth improving.
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02 / DESIGN
Define the system.
Agree on scope, architecture, permissions, approval points, and acceptance criteria.
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03 / BUILD
Build and verify.
Deliver in reviewable stages. Test expected behavior, exceptions, and failure recovery.
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04 / OPERATE
Keep ownership clear.
Define support, monitoring, documentation, escalation, and a practical way to stop or change the system.
The system can assist.
Your business stays in charge.
Consequential actions need explicit rules. Define what can proceed, what needs a person, and what must stop.
- 01 / Prepare AI drafts output
- 02 / Review Human decision
- 03 / Act Approved work proceeds
Enterprise thinking.
Close to the operator.
Boots brings more than two decades of enterprise technology and customer experience work to hands-on software delivery.
That background shapes the questions we ask: Who uses this? What happens when it fails? Who approves the action? Who maintains it?
Today, that experience informs custom applications, AI workflows, and founder-built products for businesses that need practical systems and clear accountability.
Clear answers.
Before a commitment.
What kind of company is Boots On The Ground AI?
Boots On The Ground AI is a founder-led software company based in Aurora, Illinois. We provide custom software development, AI systems, and technology consulting for small businesses and growing organizations.
Do I need to know which AI product I want?
No. Start with the work that is slow, repetitive, difficult to track, or creating risk. We map the workflow and determine whether software, AI, or a simpler process change is the right fit.
Are the portfolio products client projects?
The featured products are founder-built Boots projects. They demonstrate product design and implementation work. They are separate from client case studies and do not imply customer results.
Can I use a portfolio product in my business immediately?
Availability and access vary by product. A walkthrough establishes current capabilities and fit. Client deployment requires a separate review of requirements, integrations, security, testing, and ongoing support.
How do you price an engagement?
Custom work is scoped after reviewing the workflow, data, integrations, and operating requirements. The proposal defines deliverables, acceptance criteria, third-party costs, and any ongoing maintenance or support.
How is human oversight included?
We define what the system may do, what requires approval, when it must escalate, and how it can be paused. Controls are selected and tested for the agreed workflow and risk level.
Bring the workflow.
Let’s define the right build.
Start with a conversation about the work, the constraints, and what a useful result looks like.
What We Build
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![A computer monitor and a smartphone displaying a chatbot interface named "Boots" with conversation and login screen, situated on a white desk.]()
Custom AI Applications
Single-purpose tools that automate reporting, workflows, and daily operations, delivered in short sprints on flat pricing.
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![Diagram titled 'Entity Relationship Diagram — Boots on the Ground AI platform database schema,' showing 13 tables across 7 domains with foreign key relationships. Tables include organizations, brands, locations, org_members, pending_invitations, team_members, documents, read_outs, audit_events, and shifts, with various attributes and key indicators.]()
Understand Your Code Before You Ship
Codebase mapping and review for teams that inherited AI-generated code and need to know what's actually in it.
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![A webpage screenshot of Boot AI platform showing a process flow chart on the left and a detailed description on the right. The process flow includes stages like researcher, strategist, writer, and reviewer with corresponding activities. The right section displays a business profile with a green status indicating it is ready in 28 seconds, along with a prompt to paste a website URL.]()
AI Agents That Know Your Business
Retrieval-grounded assistants trained on your documents and policies, with cite-only answering so the AI can't invent a response, and human handoff built in.
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![Animated dog character wearing a navy blue cap with 'BOOTS' written on it, a blue sweater with 'Agent Boots' printed on it, and a headset with a microphone.]()
Voice AI
Conversational systems that answer, book, and capture leads 24/7, built by someone who has shipped voice AI at 14,000-restaurant scale.
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![Section header with yellow background saying "A GUIDED BUILD, NOT A BLANK PROMPT". Large white text says "Define the job before asking AI to do it." Below, smaller gray text explains "Structure purpose, knowledge, actions & limits — then review the result." The image includes a diagram with labeled sections, such as "Business Input" with circles for Goal, Knowledge, Audience, and Escalations, and a dark blue box labeled "Grounded configuration" with subcategories like Role and objective, Approved knowledge, Allowed actions, and Boundaries and escalation. A beige box on the right shows "Reviewable result" with details about reviewability, clear and testable output, and readiness for human review, and a button labeled "Human review retained".]()
AI Audit & Consulting Services
Engineered with the same security and audit standards we apply to regulated environments.
Who We Work With
Small and local businesses across Chicagoland, including Aurora, Naperville, Oswego, and Plainfield
GLP Toxicology Labs that need voice-driven capture for GLP preclinical studies
Local cities, Med-Spas, Home-service contractors, and any service business that runs on appointments
Real Estate Firms that need simple bookings that work part of your business - because it is.
FAQs
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Boots On The Ground AI builds custom AI applications, AI agents, and voice AI systems for small and mid-sized businesses in the Chicago area. Every system is engineered with row-level-security isolation, immutable audit trails, retrieval grounding with cite-only answering, and human review of all AI output. The company is based in Aurora, Illinois, and is a Registered partner in Anthropic's Claude Partner Network.
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Damara Carlentine is the Founder and Principal of Boots On The Ground AI. She was Senior Technical Lead and Architect of McHire, the conversational hiring platform deployed across more than 14,000 McDonald's restaurants and facilitating over 200,000 hires per year, and has spent more than 25 years building enterprise conversational and applied AI.
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Boots On The Ground AI uses flat pricing for teams of 1 to 50 rather than per-seat pricing. Engagements begin with a free AI audit and strategy consultation, and range from single-purpose AI apps built in short sprints to full automation stacks with voice AI, workflow automation, and custom agents.
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Off-the-shelf tools answer from general knowledge and can invent responses. Boots On The Ground AI systems are grounded in your own documents and policies, answer only with citations to that material, log every action to an immutable audit trail, and route uncertain cases to a person. The result is an AI system your business owns and can defend.
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Boots Sentinel is the company's flagship research platform: AI-native, voice-driven data capture for GLP preclinical toxicology laboratories, with real-time protocol-deviation detection and human-gated review before any record is finalized. It is co-developed with an operating GLP lab at a major public research university. Details at bootsagentai.com/boots-sentinel.