01
Discovery Call
15‑minute complimentary call to understand your situation, determine fit, and assign the right tier (Standard or Complex).
ComplimentaryTechnical Due Diligence for AI & Media Technology – for Investors & Operators
When millions are on the line... and the technology is ambitious, unclear, or already failing,... clients call me to know what to do next.
I validate bold technical claims before the check clears – and I rescue high‑stakes systems that have already gone off the rails.
Verify Due Diligence & Reality Checks
Rescue Recovery & Technical Leadership
Create AI Design & Character Creation
StanfordCiscoESPNNASANetflixHBOAmazonSECUSAFANetApp
For 25+ years, when systems were labeled "impossible" or "unsalvageable," I was the one responsible for making them work – from Cisco TelePresence to a $30M broadcast build that couldn't miss a second. Now I use that same judgment to protect your capital and roadmap.
— Gerard J.R. Keenan
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- Years Senior Architecture
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- Years 100% AI Focus
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- Live Streams Annually
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- Uptime Track Record
The Problem
Your AI Project Is Burning Money.
I'll Tell You Why.
Your vendor can't explain your architecture in plain English or how it actually applies to your money model. You're six months in with no production deployment. Costs are escalating with no corresponding capability. Your "AI strategy" is actually a vendor strategy. And nobody on your team can independently validate what's being built.
Signature Framework
The WildRaven Technical Reality Assessment™
7‑day senior‑level technical due diligence for AI, media, and complex software systems when millions are on the line.
One advisor. Brutally honest findings. A clear "proceed / renegotiate / fix / kill" plan – not a generic slide deck or AI‑generated "best practices."
02
Deep Technical Review
Access to architecture docs, codebase samples, vendor contracts, and key team members. I personally review everything – no junior analysts – and map the system to your business and money model.
Days 1–503
Written Technical Reality Assessment
Current‑state analysis, critical risks, time and cost to fix, and a 90‑day de‑risking outline with a clear recommendation: proceed, renegotiate, fix, or kill.
Days 5–604
Executive Briefing
60‑minute walkthrough with Q&A. Decision framework for your deal team and operators, plus recommended next steps.
Day 7Scope
What's Included & Scope
So you know exactly what you're buying.
- 1 primary product / platform
- Up to 5 core services / components
- Up to 3 repos sampled
- Up to 3 stakeholder interviews (60 minutes each)
- Remote work only; no full security or performance lab testing
If the scope is materially larger, we agree an adjusted fixed fee before proceeding.
Fee: From $7,500 (Standard) · $12,500+ (Complex)
Guarantee: If you don't feel you received senior‑level guidance worth at least what you paid, you will receive a full refund of your fee.
Services
Services Built for Real Problems
Direct access to Gerard — no junior associates, no handoffs. Every engagement is personally led.
AI / Vendor Reality Check™
$5,000 · 3–5 days
For operators about to sign a mid-six or low-seven-figure AI, media, or complex software contract.
Desired Outcome
Spot the big risks and ask the right questions before you sign, so you don't lock into a bad deal.
What's Included
- Desk review of vendor docs and proposed architecture
- Feasibility, vendor lock-in, and "fake AI" / slideware risk assessment
- 2–3 page memo with red flags and specific must-ask questions
- 30-minute executive summary call
Systems Rescue Sprint
From $15,000 · 2–4 weeks
Available after a WildRaven Technical Reality Assessment™.
Your high-stakes system is failing. I find the real causes and lead the first phase of recovery against a 60–90 day plan.
Stalled AI initiative? Vendor underperforming? Costs escalating with nothing to show? I come in, diagnose the real problem — not the symptom your team is chasing — and deliver a specific, actionable recovery roadmap.
Desired Outcome
Within 2–4 weeks: a written report with root cause, honest assessment, and a prioritized plan to fix it, pivot, or kill it — and, where engaged, coordination with your team to start executing the plan.
What's Included
- Rapid current-state assessment
- Root cause & vendor misrepresentation analysis
- Architecture & technical debt review
- Prioritized recovery roadmap
- Written report & executive briefing
Elite Advisory
Primarily for existing clients and boards.
$500/hr
On-demand senior technical counsel — I represent you, not a vendor.
You get me: a 25-year systems architect who preps independently, reviews your situation in depth, and tells you the truth — with real options, not a sales pitch. I work for you. Period.
Desired Outcome
Walk away with clarity: what's working, what's not, and exactly what to do next.
What's Included
- Pre-engagement survey & document review
- Scheduled Zoom consultation
- Written summary of findings & recommendations
- Follow-up presentation to your team (if needed)
- Architecture, vendor, AI strategy & build-vs-buy analysis
Fractional CTO
Primarily for existing clients and boards.
Typically begins after a Reality Assessment or Systems Rescue Sprint.
From $5,000/mo
Senior technical leadership without the full-time executive cost.
I embed in your organization as your technical decision-maker — owning your architecture, managing your vendors, mentoring your team, and reporting to your board. You get an executive, not a consultant. No ramp-up, no learning curve.
Desired Outcome
Consistent senior technical leadership that protects your interests, accelerates your roadmap, and prepares you for scale, fundraising, or exit.
What's Included
- Strategic technical leadership & architecture ownership
- Vendor management, evaluation & negotiation
- Team mentoring & engineering culture development
- Board-level technical reporting & investor communication
- AI strategy, roadmap ownership & build-vs-buy decisions
Create
AI Design & Character Creation
Diagnosis is half the practice. The other half is creation — designing the AI systems and characters the diagnosis says you need. Same architect, same standard: complement and amplify, never substitute or replace.
AI Character Design
Project-based · Scoped on the discovery call
Original AI characters and branded personas, designed end to end — identity, voice, personality architecture, knowledge boundaries, and the guardrails that keep them on-brand under pressure.
Built by a 25-year systems architect with a motion picture and broadcast pedigree: characters that perform like talent and operate like infrastructure.
Desired Outcome
A production-ready AI character your customers remember — consistent, safe, and unmistakably yours.
What's Included
- Character concept, identity & backstory development
- Voice & conversational personality design
- Knowledge base architecture & behavioral guardrails
- Platform implementation & live tuning
- Brand-safety review & escalation design
AI Experience Design
Project-based · Scoped on the discovery call
AI-augmented systems designed from the workflow out — voice agents, intelligent automation, and interaction design that amplifies the people who make your business run.
Under the Augmentative Intelligence philosophy: AI aimed at the choke points where it multiplies human capability, engineered with the redundancy and production discipline of broadcast-grade systems.
Desired Outcome
AI working where it actually pays — measured against a business metric, owned by you, built right once.
What's Included
- Workflow & money-model analysis
- System & interaction design
- Build or vendor-led implementation with full IP ownership
- Production rollout, telemetry & tuning
- Team handover — capability, not dependence
One standard keeps both practices honest: I never serve as the independent assessor of my own builds. Diligence clients get unconflicted judgment; design clients get the builder that judgment trained.
About
Gerard J.R. Keenan
Senior Advisor · WildRaven Strategic Advisory
Director-level AI systems architect with 25+ years building products and capabilities that didn't exist before. Named technical authority and client representative across vendor stacks and engineering teams — 100% focused on AI-augmented design since 2020.
Trusted by Stanford, Cisco, ESPN, NASA, the SEC, Netflix, HBO, and Amazon. Brings rigorous systems engineering, technology-agnostic judgment, and a philosophy that AI must complement and amplify — never substitute or replace.
"AI must complement and amplify, not substitute or replace."
— Augmentative Intelligence Philosophy
- Cisco TelePresence — prototype → multi-billion-dollar product line
- ESPN LA Live — 28-engineer team, 35,000 man-hours
- StreamingTennis.com — 1B+ live streams, 99.97% uptime
- NASA — first cross-continental live streaming under security clearance
- SEC — mission-critical live streaming, 99.99%+ uptime
- Wealth Management AI — $1B+ investment capital
Resources
Resources
Frameworks, checklists, and thought leadership from 25+ years of systems architecture.
The WildRaven Technical Reality Assessment
Our forensic 7-day methodology for rapid technical clarity.
Read the PDF →5 Signs Your AI Initiative Is Failing
And what to do about it — before it's too late.
Read the PDF →Technical Due Diligence Checklist
The investor's guide to evaluating AI investments.
Read the PDF →The Fractional CTO Advantage
Senior technical leadership without the full-time cost.
Read the PDF →Engagement Facts
Common Questions
- Firm
- WildRaven Strategic Advisory — technical due diligence for AI & media technology, for investors & operators, led by Senior Advisor Gerard J.R. Keenan.
- Who It's For
- Investors, boards, and operators evaluating AI, media, and complex software systems — or rescuing high-stakes systems that have gone off the rails.
- Signature Engagement
- The WildRaven Technical Reality Assessment™ — 7-day senior-level technical due diligence, from $7,500 (Standard) or $12,500+ (Complex).
- How To Start
- A complimentary 15-minute discovery call. Email [email protected] or call 310.570.0774.
What is technical due diligence, and when do I need it?
Technical due diligence is an independent review of a system's architecture, code, vendors, and delivery risk before capital is committed. You need it when you're about to sign a large AI, media, or software contract, when you're investing in or acquiring a technology company, or when an existing build is behind schedule and you can't get a straight answer about why.
How long does the WildRaven Technical Reality Assessment™ take?
Seven days. It starts with a complimentary 15-minute discovery call to determine fit and tier. Days 1–5 are the deep technical review of architecture docs, codebase samples, vendor contracts, and key team members. Days 5–6 produce the written Technical Reality Assessment. Day 7 is a 60-minute executive briefing with Q&A.
What does an engagement cost?
The Technical Reality Assessment starts at $7,500 (Standard) and $12,500+ (Complex). The AI / Vendor Reality Check™ is $5,000 over 3–5 days. Systems Rescue Sprints start at $15,000 over 2–4 weeks. Elite Advisory is $500 per hour with a 2-hour minimum. Fractional CTO engagements start at $5,000 per month with a 10-hour monthly minimum and 3-month commitment. If scope is materially larger, an adjusted fixed fee is agreed before proceeding.
Who actually does the work?
Gerard J.R. Keenan, personally. There are no junior analysts and no handoffs — every engagement is personally led. That is why scope is capped at 1 primary product or platform, up to 5 core services or components, up to 3 repos sampled, and up to 3 stakeholder interviews of 60 minutes each.
What do I receive at the end of an assessment?
A written Technical Reality Assessment covering current-state analysis, critical risks, time and cost to fix, and a 90-day de-risking outline — with a clear recommendation: proceed, renegotiate, fix, or kill. Not a generic slide deck or AI-generated "best practices."
Are you independent of the vendors you review?
Yes. WildRaven represents the client, not a vendor. In Gerard's words: "I work for you. Period." Findings are brutally honest, technology-agnostic, and delivered with real options rather than a sales pitch.
What kinds of systems do you assess?
AI and machine learning platforms, live and on-demand video and broadcast infrastructure, streaming and media delivery systems, and complex enterprise software. Prior delivery work includes systems for Stanford, Cisco, ESPN, NASA, Netflix, HBO, Amazon, the SEC, USAFA, and NetApp.
Is there a guarantee?
Yes. If you don't feel you received senior-level guidance worth at least what you paid, you will receive a full refund of your fee.
Do you also design and build — or only assess?
Both. Alongside due diligence and rescue work, WildRaven designs and builds AI systems and original AI characters — identity, voice, personality architecture, and guardrails — as a distinct Create practice. The two are kept honest by one rule: I never serve as the independent assessor of my own builds, so diligence clients always get unconflicted judgment.
Do you work remotely or on site?
Assessment engagements are remote, which is what keeps the 7-day timeline realistic. Full security auditing and performance lab testing are outside standard scope. Fractional CTO engagements embed Gerard in your organization as your technical decision-maker.
Contact
Ready to get the truth
about your technology?
Start with a complimentary 15-minute discovery call. No pitch, no pressure — just an honest conversation about your situation.
Or reach out directly