WildRaven Advisory
Technical Due Diligence for AI & Complex Software 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.
Schedule a CallFor 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
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 & complex software when $5–$50M is on the line.
One advisor. Brutally honest findings. A clear "proceed / renegotiate / fix / kill" plan – not a deck full of frameworks.
Discovery Call
15-minute complimentary call to understand your situation, determine fit, and assign the right tier (Standard or Complex).
ComplimentaryDeep Technical Review
Access to architecture docs, codebase samples, vendor contracts, and key team members. I personally review everything – no junior analysts.
Days 1–5Written Technical Reality Assessment
Current-state analysis, critical risks, cost and time to fix, and a 90-day de-risking plan with a clear recommendation: proceed, renegotiate, fix, or kill.
Days 5–6Executive Briefing
60-minute walkthrough with Q&A. Decision framework for your deal team and operators, plus recommended next steps.
Day 7Fee: From $7,500 (Standard) · $12,500+ (Complex)
Guarantee: If you don't feel you received senior-level guidance worth at least 10× the fee, I refund you.
Services
Services Built for Real Problems
Direct access to Gerard — no junior associates, no handoffs. Every engagement is personally led.
Technical Due Diligence
From $7,500
Know what's real before you write the check.
Independent, technology-agnostic evaluation of a target company's technical assets, AI capabilities, architecture, and team. I give investors and acquirers the ground truth — what actually works, what's smoke, and what it will really cost to scale.
Desired Outcome
Written report for your board or deal team delivered within 48–72 hours. Team presentation available for an additional fee.
What's Included
- Deep architecture & AI/ML capability assessment
- Vendor stack & platform dependency risk analysis
- Scalability, technical debt & total cost of ownership
- Written report for board / investor consumption
- Optional: live presentation to deal team
Delivered in 48–72 hours · Price determined by project scale & complexity · Starts with a complimentary 15-minute discovery call
Schedule a Discovery CallThe "Rescue" Sprint
$5,000 flat
Your project is on fire. I find out why and hand you a recovery 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 1–2 weeks: a written report with root cause, honest assessment, and a prioritized plan to fix it, pivot, or kill it.
What's Included
- Rapid current-state assessment
- Root cause & vendor misrepresentation analysis
- Architecture & technical debt review
- Prioritized recovery roadmap
- Written report & executive briefing
1–2 week engagement · Starts with a complimentary 15-minute discovery call
Schedule a Discovery CallElite Advisory
$500/hr
On-demand senior technical counsel — I represent you, not a vendor.
You get 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
2-hour minimum · Starts with a complimentary 15-minute discovery call
Schedule a Discovery CallFractional CTO
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
10-hour monthly minimum · 3-month minimum commitment · Starts with a complimentary 15-minute discovery call
Schedule a Discovery Call
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
Resources
Resources
Frameworks, checklists, and thought leadership from 25+ years of systems architecture.
The 48-Hour Technical Reality Assessment
Our signature methodology for rapid technical clarity.
Contact for details5 Signs Your AI Initiative Is Failing
And what to do about it — before it's too late.
Contact for detailsTechnical Due Diligence Checklist
The investor's guide to evaluating AI investments.
Contact for detailsThe Fractional CTO Advantage
Senior technical leadership without the full-time cost.
Contact for detailsContact
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.
Book Your 15-Minute Discovery CallOr reach out directly