Boots On The Ground AI · Development Workshop
AI product development for operational workflows.
Boots On The Ground AI helps software companies and operations teams turn complex workflows into working AI products. Founder Damara Carlentine leads discovery, architecture, implementation, and handoff herself — drawing on enterprise conversational AI experience and a production platform delivered end to end, in the open.
Woman-Owned Small Business (WOSB) certified · Aurora, Illinois · Serving clients nationwide
Commits in one production build — 157 authored by the founder
Merged pull requests, each specified, built, and reviewed
Database migrations, from tenant isolation to booking
Automated tests passing at the full-stack audit, July 12, 2026
From the Boots platform build record, February–July 2026. Every figure reproduces from the repository — read the full case study. These numbers measure delivery, not promised outcomes; that distinction is the point.
What we build
Production systems, not prototypes that demo well.
Four of the ten builds on our pricing page — each scoped in writing before work begins, each shipped with the security controls its risk requires. Security is not an optional upgrade.
Secure Knowledge Assistant
Answers grounded in approved organizational knowledge, with source visibility — and honest handling when the documents don’t support an answer.
Typical build $4.5K–$10KVoice & Front Desk AI
Call handling, qualification, and follow-up with defined escalation paths — for teams whose customers still pick up the phone.
Typical build $4.5K–$10KCustom AI Operations App
A purpose-built system for a workflow off-the-shelf software cannot handle — multi-tenant, permissioned, and operated like a product, not a project.
Starting at $15KProposal-to-Cash System
Discovery, proposal, approval, agreement, and payment connected into one workflow — the system this practice runs on itself.
Typical build $7.5K–$18KAlso: website design & development, customer reactivation, document transformation, AI readiness & risk audits, governance controls, and fractional Chief AI Officer engagements — see all ten, with pricing.
One practical path, problem to supported system.
No mystery bundles. No unlimited support promises. No detailed architecture given away during a free sales call. Scope, ownership, third-party costs, and human-control boundaries are documented before build.
Featured build · Boots Command Center
From product idea to a working AI system.
The Command Center is a system we designed and built for our own operations — clients, projects, tasks, notes, playbooks, products, assets, and AI resources in one secure workspace. It is shown here because it demonstrates the work: scattered business knowledge, organized into one grounded operating view, with the operator in control.
Before: knowledge and work everywhere
After: one grounded command center
Illustrative workflow visualization; not a measured performance claim.
Know what is active
One dashboard shows the clients, products, projects, campaigns, notes, and tasks that need attention.
Keep knowledge usable
Playbooks, skills, agents, notes, and business assets stay organized, so important context is available when the work begins.
Connect work to context
Client information, project activity, product details, and supporting material stay close enough to make informed decisions.
Reduce tool sprawl
An improvised collection of trackers and folders becomes a workspace designed around how the business actually operates.
Your system. Your control.
The Command Center organizes the work and makes business context easier to reach. It does not remove operator judgment or decide what matters for you.
Founder operating system
Product ideas, client delivery, business assets, working notes, and next actions inside one dependable view.
Consultancy command center
Client context, projects, deliverables, reusable playbooks, service products, and marketing activity, organized.
AI builder workspace
A visible inventory of agents, skills, technical playbooks, project knowledge, and the work they support.
Open Boots Command Center — or picture this workspace built around your operation, and start that conversation.
Golden sets, acceptance gates, and reproducible evidence — before a system ships, not after it embarrasses someone.
Adversarial testing of our own production systems first: threat models, leakage tests, human-gate checks.
Tenant isolation, audit trails, and fail-visible engineering as defaults, documented per system.
Registries, review cadences, and disclosure discipline aligned to the NIST AI RMF and federal AI requirements.
The four-playbook defensive-AI library — evaluations, red-teaming, secure deployment, governance — is the method behind every build on this page, and the basis of our federal contracting practice, detailed under Services. It is also how the Boots platform itself was delivered: the case study is the evidence.
Founder-led, by design
The person who scopes it is the person who builds it.
No handoff to a junior team after the sales call. Damara Carlentine — founder and principal of Boots On The Ground AI, LLC — leads discovery, architecture, implementation, and handoff on every engagement, and documents the work so your team can run it without her.
Former Senior Technical Lead and Architect of McHire, the conversational hiring platform deployed across more than 14,000 McDonald’s restaurants.
Enterprise conversational and applied AI delivery, from architecture through production operations.
157 of 160 commits and 104 of 107 pull requests on the Boots platform are hers — the record is published, dated, and checkable in the case study.
Questions
Asked, answered.
What does Boots On The Ground AI build?
Production AI products for operational workflows: document-grounded knowledge assistants with citations, voice and front-desk AI, AI features inside multi-tenant products, proposal-to-cash systems, and custom operations applications — ten scoped builds, all with published pricing ranges.
How does an engagement start?
With a short fit call, then — when the workflow, integrations, or risk are not yet defined — the Grounded AI Blueprint: a fixed-scope diagnostic that returns a documented assessment and a phased plan (typically $1,500 for a local business). Any build that follows is scoped and priced separately, in writing. Tightly scoped work may move directly to a proposal after the fit call.
Who actually builds it?
Damara Carlentine, the founder. She leads discovery, architecture, implementation, and handoff on every engagement — the same person who designed and delivered the Boots platform documented in the case study — and documents the work so your team can operate the system without her.
What is Boots Command Center?
A centralized business workspace for managing clients, products, playbooks, assets, marketing activity, notes, tasks, projects, skills, and agents through one easy login. We built it for our own operations; it is featured on this page as an example of the work, and systems like it can be built around your operation.
Does AI make decisions automatically?
No. Our systems organize knowledge, draft, retrieve, and recommend — with human review points designed in. The operator remains responsible for priorities, approvals, and consequential business decisions.