Custom AI & Fractional CAIO · The Flagship

Proprietary AI. Senior leadership. Governance built in.

For firms whose ambitions outgrow off-the-shelf tools and whose obligations demand more than vendor terms-of-service. We build custom AI applications, internal copilots trained on your firm’s knowledge, and ML models with secure data pipelines. A governance layer is scoped to your regulatory posture: bar advertising rules, HIPAA, SEC/FINRA, fair housing. Fractional Chief AI Officer leadership wraps it all.

Bar · HIPAA · SEC/FINRA · Fair-housing posture
Your data stays in your environment
Founder-led, senior-only delivery
Capabilities

Five capabilities.
One accountable owner.

Most engagements begin as a defined-scope project or a fractional CAIO retainer that sequences these over time. Each card jumps to the detail below.

Custom AI Applications
Proprietary advantage

Internal copilots · Document analysis · Intake triage

Custom AI Applications

Copilots trained on your knowledge, not the internet's.

The AI your competitors can subscribe to is, by definition, not an advantage. Custom applications are. We build internal copilots trained on your firm's precedents and protocols. We build document-analysis pipelines tuned to your matter types, intake triage that applies your qualification logic, and research assistants that answer from your knowledge base with citations.

  • Internal copilots trained on the firm's own knowledge base
  • Document analysis and first-pass drafting from your templates
  • Intake triage that applies your qualification and conflict logic
  • Research assistants with source citations from your corpus
  • Retrieval infrastructure (vector stores, document pipelines) sized to the firm
  • Deployed in your environment when data cannot leave it

Every proposal is written to your firm. We do not publish a public menu.

Ask about this
ML Models & Data Pipelines
Built to last

Data infrastructure · Bespoke models · Evaluation

ML Models & Data Pipelines

Models are only as good as the pipelines beneath them.

Most AI initiatives fail below the waterline: inconsistent data, no evaluation discipline, pipelines nobody owns. We build the unglamorous parts properly: ingestion, cleaning, feature pipelines, model evaluation, and monitoring. That way the model layer on top stays accurate, auditable, and maintainable for years.

  • Data ingestion, cleaning, and feature pipelines
  • Bespoke ML models where off-the-shelf inference falls short
  • Evaluation harnesses, accuracy measured before and after every change
  • Monitoring and drift detection in production
  • Security-first architecture, encryption, access control, audit logging
  • Documentation and handoff your future team can actually maintain

Every proposal is written to your firm. We do not publish a public menu.

Ask about this
AI Strategy & Governance
Deploy with confidence

Audits · Policy · Vendor selection · Training

AI Strategy & Governance

A framework, not a memo.

Leadership doesn't need another AI think-piece. It needs a working governance layer. That means an honest audit of current usage (sanctioned and shadow), acceptable-use and data-handling policy people can follow, vendor evaluation with contractual teeth, and role-specific training. That's what lets a regulated firm say yes to AI without betting the license on it.

  • AI usage audits, including shadow-AI discovery
  • Governance frameworks and acceptable-use policies
  • Vendor selection, contract review, and DPA/BAA requirements
  • Role-specific team training and leadership briefings
  • Risk registers mapped to your regulatory posture
  • Change management for firm-wide rollouts

Every proposal is written to your firm. We do not publish a public menu.

Ask about this
Fractional Chief AI Officer
Senior leadership

Strategy · Architecture · Vendor governance · Accountability

Fractional Chief AI Officer

C-suite AI ownership without the C-suite seat cost.

Most professional firms need senior AI leadership a few days a month, not a full-time executive. The fractional CAIO retainer puts one accountable owner on the whole agenda: strategy and roadmap, architecture decisions, vendor governance, hiring support, and reporting. Reporting comes in business terms (booked consultations, hours saved, risk retired), not model jargon.

  • AI strategy and quarterly roadmap ownership
  • Architecture and build-vs-buy decisions, justified in writing
  • Vendor governance, evaluation, contracts, renewals
  • Hiring support for AI-adjacent roles
  • Board- and partner-level reporting in business terms
  • Continuity across projects, one owner, not serial consultants

Every proposal is written to your firm. We do not publish a public menu.

Ask about this
Security & Compliance Architecture
Regulated by design

HIPAA · Bar rules · SEC/FINRA · Fair housing

Security & Compliance Architecture

Architecture that respects the rules your firm lives under.

The same AI system that's fine for an e-commerce brand can be a reportable incident for a medical practice. We architect per posture. That means HIPAA-aware systems with BAAs and encrypted PHI handling, bar-aware systems with UPL and confidentiality guardrails, SEC/FINRA-conscious workflows for wealth managers, and fair-housing-conscious AI for real estate.

  • HIPAA-aware architectures, BAAs, encrypted channels, no PHI in non-compliant LLMs
  • Bar-aware systems, confidentiality, UPL guardrails, advertising-rule review
  • SEC/FINRA-conscious workflows, marketing rule and books-and-records constraints
  • Fair-housing-conscious AI for real estate applications
  • Family-office discretion and privacy controls
  • Audit trails and documentation on every interaction

Every proposal is written to your firm. We do not publish a public menu.

Ask about this
Start Here

A ladder, not a leap.

Most firms don’t start with a retainer. They start with a free read, then take one graduated, low-risk step at a time. Each step is a real piece of governance work, not a sales call. Climb only as far as you need. The $497 AI Use Policy Kit credits in full toward the $2,500 Bootstrap.

Learn & diagnose

Free

AI Executive Readiness Assessment

A self-scored diagnostic across six governance pillars: a 0 to 100 score, a readiness band, and your lowest-scoring pillar. Paired with the 7 Resistance Signals listicle.

Take the Assessment

$4.97

AI-Ready Change Management Playbook

The senior method for leading governed AI adoption inside a regulated firm, with a 40-prompt companion pack. Credits toward the Governance Snapshot.

Get the Playbook

$14.97

AI Governance Snapshot

A 15-minute live posture read with Brandon: Exposed, Uneven, or Governed, measured against the four-phase model. Comes with the prep reading that anchors the call.

Book the Snapshot

Then build

$97

Founder-Led Stack & Policy Audit

A written 4-page memo: shadow-usage exposure, a sanctioned-stack recommendation, and one vertical-compliance gap. Plus the “Ask Brandon” roundtable.

Book

$197

In-Office AI Policy Workshop

A 3-hour small-group build session; each attendee leaves with a firm-branded draft AI Use Policy to circulate.

Book

$497 · Done for you

AI Use Policy Kit

We deliver a ratifiable, firm-branded AI Use Policy doc + Sanctioned Tools list in 5 to 10 days. Credits in full toward the Bootstrap.

Start

$2,500

90-Day CAIO Bootstrap

Baseline governance installed: sanctioned stack, ratified policy, staff-posture memo, one copilot pilot. A prior Kit credits in, so the net is $2,003. Fractional CAIO retainer (from $4,000/mo) and Custom AI projects (from $15,000) scope from here.

See Pricing

Built for your industry

See how this applies to your firm

Every vertical has its own page with a free diagnostic scan calibrated to its rules and its language.

All industries we serve
Begin

Who owns AI at your firm?

If the honest answer is “nobody, really,” that’s the gap, not the tools. Start with the readiness assessment, or bring the question straight to a consultation.

or call 305-209-8453 · se habla español

For informational and educational purposes only

This assessment produces automated, directional results based on the information you provide and the current version of our scoring rubric. Outputs are educational and informational only, not guarantees, predictions of outcome, or professional advice. Results can change between runs as the rubric or scan data is updated. This tool is not a substitute for advice from a licensed professional in your jurisdiction. Nothing produced by this tool is legal, medical, tax, financial, or investment advice. AI-generated content in this tool (including any narrative summary written by a large language model) may be inaccurate, incomplete, or out of date; verify anything you plan to act on with a licensed professional in your jurisdiction. AI assistants (ChatGPT, Perplexity, Gemini, Google AI Overviews, Claude) independently determine which firms or sources they cite. No vendor can guarantee specific AI outputs, citation frequency, or search rankings. By using this tool you acknowledge these limitations.

FAQ

Custom AI & Fractional CAIO, FAQ

What does a fractional Chief AI Officer actually do?

Everything a full-time CAIO would, at a fraction of the seat cost. A fractional CAIO owns the AI strategy and roadmap. They govern vendor selection and contracts, make architecture decisions, and set acceptable-use and data-handling policy. They support AI-related hiring and report progress in business terms leadership can act on. For most professional firms (a 10-partner law firm, a 6-physician concierge practice), the AI agenda needs senior ownership a few days a month, not a $300K+ full-time executive.

When does a firm need custom AI instead of off-the-shelf tools?

Three triggers. First, when your obligations outgrow vendor terms of service. Client-confidential legal documents or PHI shouldn't flow through consumer AI tools. Second, when the value is in your proprietary knowledge. A copilot trained on your firm's precedents, protocols, or playbooks compounds in a way a generic subscription never will. Third, when workflow fit matters. Off-the-shelf tools automate generic tasks; custom AI automates yours. If none of the three apply yet, we'll tell you to keep the subscriptions.

How do you handle HIPAA, bar rules, and SEC constraints in AI systems?

Governance is designed in, not bolted on. For healthcare: PHI is processed under a signed BAA, transmitted via encrypted channels, and never routed through non-compliant LLMs. For law firms: systems respect confidentiality and UPL guardrails, with advertising-adjacent outputs reviewed against Florida Bar Rules 4-7.11 through 4-7.22 and ABA Model Rules where applicable. For wealth managers: SEC marketing-rule and books-and-records constraints shape what the AI may generate and what gets logged. Every system ships with audit trails.

What does custom AI work cost?

Custom engagements are scoped individually. We do not publish a public menu because no two firms' data, risk posture, and workflow are alike. Most work begins one of two ways. One is a defined-scope project: a copilot, a document-analysis pipeline, or a governance framework. The other is a monthly fractional Chief AI Officer retainer that sequences the roadmap over time. Either path starts with the free AI Executive Readiness Assessment. It shows where your firm stands across six pillars before anyone writes a proposal. See pricing.

What is an internal copilot, concretely?

A private AI assistant trained on your firm's own knowledge base: precedents, SOPs, intake histories, and research memos. Your team queries it in plain language. A law-firm copilot drafts first-pass documents from your templates and flags conflicts. A medical-practice copilot answers protocol questions from your own clinical standards. A wealth-management copilot summarizes client files within your compliance perimeter. Your data stays in your environment, and the copilot's knowledge compounds as the firm's does.

Which AI models and platforms do you build on?

We're vendor-neutral by design. That's half the point of the governance work. The mix depends on your security posture and workload. Builds draw on frontier models (Anthropic Claude, OpenAI, Google Gemini) via their enterprise APIs. They use open-weight models run in your own environment when data cannot leave it. And they use retrieval infrastructure (vector stores, document pipelines) sized to the firm. Model choice is an architecture decision we justify in writing, not a default.

How do we know if our firm is ready for any of this?

Take the free AI Executive Readiness Assessment. It is a self-scored diagnostic across six pillars: strategy, governance, data, security, team, and adoption. It produces a 0 to 100 score, a readiness band, and your lowest-scoring pillar. It takes about ten minutes. You can attach the results directly to a strategy-session request, so the first conversation starts from evidence instead of generalities.

Can you train our team instead of building for us?

Yes. Enablement is a standard governance deliverable. That includes leadership briefings, role-specific training on approved tools, acceptable-use policy rollout, and change management. If you're planning a rollout, the $4.97 AI-Ready Change Management Playbook covers the sequencing we use: readiness, pilot selection, policy, training, and measurement. It is the first paid rung of the CAIO ladder and comes with a 40-prompt companion pack.

What does a Fractional CAIO retainer cost?

Two retainer tiers. The Signature retainer starts at $4,000 per month and covers AI strategy and quarterly roadmap ownership, vendor governance, architecture decisions, and board-level reporting in business terms. The Estate retainer starts at $8,000 per month and adds active build management, team training, and custom-project execution within the retainer. Custom AI project engagements scope from $15,000 depending on scope, data complexity, and compliance requirements. Every path starts with the free AI Executive Readiness Assessment so the first conversation is grounded in evidence.

How do you protect sensitive data in a custom AI system?

Three-layer architecture for regulated firms. First, data-path isolation: PHI is processed under a signed Business Associate Agreement, transmitted through encrypted channels only, and never routed through a non-compliant LLM. This applies to all healthcare clients and aligns with HIPAA 45 CFR Part 164 requirements. Second, model selection: open-weight models (such as Llama 3 or Mistral variants) can be deployed entirely within the firm's own environment when data cannot leave it. Third, access control: role-based permissions and full audit trails on every AI interaction, so there is always a record of what was queried and what was returned.

What is the four-phase AI governance model?

Phase 1 is Exposed: tools are in use but there is no sanctioned stack, no policy, and leadership has limited visibility into what the team is doing with AI. Phase 2 is Uneven: some structure exists but adoption is inconsistent across the firm. Phase 3 is Governed: documented acceptable-use policy, sanctioned tools, training complete, and a named governance owner. Phase 4 is Native: AI is a core part of operations with metrics, continuous improvement, and board-level accountability. The free AI Executive Readiness Assessment diagnoses which phase your firm is in. The $14.97 AI Governance Snapshot translates that into the three most critical action items.

How long does a custom AI application take to build?

Most copilot and document-analysis projects ship in 6 to 12 weeks from kickoff. That timeline typically breaks down as: 2 weeks for discovery and architecture (understanding the firm's data, workflow, and security posture), 3 to 5 weeks for build and iteration (model selection, retrieval pipeline, interface, integration testing), and 1 to 2 weeks for compliance review and a monitored soft launch. Larger projects involving multiple pipeline stages, BAA review, or regulatory sign-off take longer. We scope each project individually and put the timeline in writing before work begins.

What is an AI use policy and why does every firm need one now?

An AI use policy is a firm-branded document that defines which tools are sanctioned, what data may flow through them, what outputs require human review before use, and what happens when the policy is violated. Without one, firms face three concrete risks: shadow AI (staff using consumer tools like ChatGPT with client-confidential data), documentation gaps during regulatory examinations (bar audits, HIPAA audits, SEC examinations expect evidence of governance), and liability when AI-generated content carries the firm's name but nobody reviewed it. The $497 AI Use Policy Kit delivers a ratifiable draft in 5 to 10 days, written for the firm's specific regulatory posture.

Can AI help with document review at a law firm without creating unauthorized practice of law issues?

Yes, with the right architecture. Custom document-analysis AI performs first-pass privilege review, extracts key terms, flags inconsistencies across contract versions, and drafts summaries from the firm's own templates. All of this operates as an attorney productivity tool, not a legal advice system. The AI does not communicate with clients, does not give advice, and every output is reviewed by an attorney before use. Systems are scoped against Florida Bar Rules 4-5.3 (responsibilities regarding non-attorney assistants) and relevant ABA Model Rules so the attorney-supervision requirement is embedded in the workflow, not left to chance.

What is retrieval-augmented generation and why does it matter for professional firms?

Retrieval-augmented generation (RAG) is the architecture that lets an AI model answer questions using the firm's own documents rather than general training data. When a staff member queries the copilot, the system retrieves the most relevant chunks from a vector store of the firm's precedents, SOPs, intake histories, and memos, then feeds them to the language model as grounded context. The result is a copilot that cites the firm's own protocols with attribution rather than hallucinating from general knowledge. For a 10-partner law firm this means the copilot answers from that firm's matter history. For a 6-physician concierge practice it means the copilot references that practice's own clinical protocols.

Does my firm have to start with the readiness assessment?

No. But most firms that skip it spend the first consultation describing symptoms rather than gaps. The free AI Executive Readiness Assessment scores six pillars in ten minutes: strategy, governance, data readiness, security posture, team capability, and adoption readiness. It produces a 0 to 100 score, a readiness band, and your single lowest-scoring pillar. Most firms discover their biggest gap is not the one they expected. Starting from that data makes the first scoping conversation specific rather than exploratory.

Aday Interactive, Inc. provides custom AI, AI governance, intelligent growth systems, and AI search visibility (GEO/AEO/SEO) for established professional firms across the United States. Founder-led from Coral Gables, FL, with in-person engagements available throughout Miami-Dade County (Coral Gables, Brickell, Coconut Grove, South Miami) and remote delivery nationwide.