AI Advisory & Virtual CTO Services
We make AI safe and useful for firms that cannot afford to get it wrong, and we run the technology leadership behind it. We do not sell tools. No resale, no vendor commissions.
What we don't do
Our advice is our own. We point you to what you need, not what we sell.
More software often means more pain. We pick the simple path.
We pick outcomes and clear calls over long decks and busy dashboards.
How firms work with DoubleChecked
AI is the sharpest edge of one independent firm. Behind it sits the same senior technology leadership we have always provided. Most clients use them together, from one team.
AI Advisory & Governance
Claude rollouts, data classification, document automation, and governance built to survive an audit or an examination. Flat fee with defined scope, from discovery to pilot to an optional retainer.
Virtual CTO Advisory
A senior tech voice in your team (also called fractional CTO). We sit at your senior table. We own the plan. We ride herd on vendors. We hold the work to 90-day beats. No long deal needed.
Our highest-value work, and the reason most firms call us now. For regulated and high-stakes firms, we govern AI and put it on terms you control: data classification, enterprise-grade Claude with no-training commitments, and document automation with audit trails. Independent, with no resale and no vendor commissions.
Typical Engagements
- Claude Teams and Enterprise rollout, training, and certification
- Enterprise AI configuration with no-training commitments, SSO, and retention controls
- AI document automation with verification and audit trails
- Examination-ready AI governance and data classification
- Fractional Chief AI Officer leadership
Senior tech help for firms that need a real lead but cannot bring on a full-time hire yet. We sit at your senior table. We own the tech work. We make sure each task lands.
Typical Engagements
- Leadership team cadence & reporting
- Ownership mapping & accountability
- Vendor strategy & management
- Meeting rhythm & performance tracking
- Risk leadership & board reporting
We go past day-to-day IT help to build a real tech plan. We size up where you stand. We name the moves that matter most. We hand you a roadmap that ties to your firm's goals.
Typical Engagements
- Current-state technology assessment
- System upgrade roadmap & budgeting
- Cost rationalization & audit
- Build vs. buy guidance (off-the-shelf vs. custom)
- Fixing hidden bottlenecks slowing your team
We go past "install antivirus" to true risk work at the senior level. We help you see your real risk. We help you meet audit rules. We help you sleep at night.
Typical Engagements
- Executive risk review & scoring
- Security program direction
- Policy & governance framework
- Breach response planning & rehearsal
- Compliance roadmap (SOC2, ISO, HIPAA)
Tech is no help if it adds friction. We simplify the way you work. We tie your systems together. We make sure your tools work for your team, not against it.
Typical Engagements
- Systems/process friction analysis
- Workflow redesign & automation
- Tooling simplification & integration
- Software subscription cleanup & savings
- Change management support
Not sure your IT shop gives you a fair deal? Our outside MSP audit checks your contract, service, security, tech calls, and vendor work. You get a written report with scored findings and a clear next-step plan.
Typical Engagements
- Contract & commercial review
- Service delivery assessment
- Security posture verification
- Technology stack review
- Relationship & governance health
Most firms have tech. Most firms do not have a plan for it. We build IT plans that tie each tech spend to your firm's goals. We hold each owner to the work.
Typical Engagements
- Current state technology assessment
- Gap analysis & 90-day roadmap
- Vendor review & contract evaluation
- Build vs buy decision support
- Board-ready executive reporting
Do not hire a tech lead on a gut feel. Our CTO-led search helps you set the role, grade real tech skill, and land a hire who fits your team and your plan. Built into our advisory work.
Typical Engagements
- Role definition & requirements mapping
- Technical competency assessment
- Candidate vetting by CTO-level advisors
- Cultural & leadership fit evaluation
- Onboarding transition support
AI Readiness Checklist
The questions every regulated firm should answer before adopting AI
The Regulated Firm's AI Readiness Checklist
Six questions that decide whether your firm can adopt AI without putting client data, a renewal, or an examination at risk. Walk them before your next audit, not after.
- Where client data is leaving your environment through personal AI accounts
- Whether your AI controls would survive a SOC 2 audit or an examination
- Where a human, not the model, needs to ratify the output
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Find out where your firm stands.
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