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John C. Derrick | Fractional CTO | Irmo, South Carolina | 2026
I architect systems for businesses that need enterprise-scale results without enterprise-scale overhead.
23+ years of legacy knowledge meets modern AI execution. I've built platforms reaching 15M+ annual users and software with 3M+ downloads. Now, I apply that same systems thinking to help small teams leverage agentic AI for competitive advantage.
The Oak Haven Advantage: I work from a purpose-built environment on 35 acres in rural South Carolina, optimized for deep focus and high output. No office overhead. No organizational drag. Just strategic clarity and hands-on execution.
My philosophy: "Effectiveness is the measurement of truth." Everything I build is designed to deliver measurable results, not theoretical possibilities.
I'm a daily practitioner of multiple AI platforms (Claude/Claude Code, ChatGPT, Gemini, and others), bringing hands-on understanding of each model's strengths and limitations. Beyond AI, I offer deep expertise in email marketing (200K+ subscribers built), affiliate monetization (CJ/Expedia, FareHarbor partnerships), and JavaScript-based automation. I don't sell theory - I build with these tools every day.
Minimum engagement: 2 hours
Billing: 30-minute increments after initial session
A focused, fully async assessment of a single workflow or process. You send documentation of how it currently works — I send back a written analysis of what's broken, what to automate, and what to ignore.
Turnaround: 3-5 business days from submission
Format: Fully async — no calls required. Written in, written out.
Best for: Business owners who have a specific bottleneck they want evaluated before committing to a larger engagement
A fixed-scope, fixed-price diagnostic for one specific workflow or operational bottleneck. You know something isn't working — this tells you exactly what to fix first and where AI fits in.
Timeline: 5 business days from discovery call to delivery
Scope: One workflow or bottleneck — not the full business. Need the full picture? That's the AI Readiness Audit below.
Best for: Business owners who know they need AI but don't know where to start — this solves the blank-page problem and gives you a concrete plan to act on
A 10-day intensive analysis of your business operations and technical stack to identify high-ROI automation opportunities.
Timeline: 10 business days from kickoff to delivery
Best for: Businesses earning $500K-$5M annually who know they're leaving efficiency on the table but aren't sure where to start
Ongoing technical leadership without the full-time executive salary.
Contract terms: 3-month minimum, then month-to-month
Typical client profile: 5-15 person teams navigating growth, AI adoption, or technical transitions
Full-stack development, AI integration, and system modernization projects.
A brand-aligned AI chatbot that lives on your website, understands your content, and actually converts visitors. I handle the full build, deployment, and ongoing management — you get a working system without learning the underlying platform.
Setup timeline: 5-10 business days from kickoff to live deployment
Built on production experience: I've deployed RAG chatbots on my own properties — including a tour concierge on HawaiiGuide.com that suggests FareHarbor experiences and a brand-aligned assistant on this site. These aren't demos; they're revenue-generating systems I operate daily.
Best for: Content-driven businesses, e-commerce sites, and service businesses that want AI-powered customer engagement without building or managing it themselves
Moving beyond chatbots into autonomous business processes. I design systems where AI agents handle repetitive cognitive tasks - content generation, data analysis, operational automation - freeing your team for high-value work.
20+ years building and operating HawaiiGuide.com (15M annual visitors). I understand how to maintain search equity while modernizing systems, migrate content without losing rankings, and structure platforms for sustainable organic growth in an AI-first world.
Refactoring dated architectures (ExpressionEngine, early PHP, outdated CMSs) into modern, AI-integrated stacks without breaking existing functionality or losing SEO value. I've migrated systems serving millions of users while maintaining 99.9% uptime.
Design operational architecture that allows small teams to achieve enterprise-level results. Strategic tooling, cognitive scaling, infrastructure that actually works - not just impressive on paper.
200K+ subscribers built across multiple properties. Expert in segmentation, behavioral automation, JavaScript-based workflows, and AI-enhanced personalization. I build email systems that convert without feeling spammy.
Revenue optimization through strategic partnerships with major networks (CJ/Expedia, FareHarbor) and vertical-specific affiliates. I design monetization systems that align with user experience and maintain editorial integrity.
Daily hands-on experience with Claude/Claude Code, ChatGPT, Gemini, Manus, and emerging models. I don't sell AI theory - I use these tools daily and understand which model solves which problem. Real implementation experience, not consultant buzzwords.
Production RAG (Retrieval-Augmented Generation) implementations for customer service, content discovery, and monetization. Built tour concierge tools suggesting FareHarbor experiences and brand-aligned chatbots for website representation in AI responses. Experience with CustomGPT.ai and modern RAG architectures that actually convert visitors into customers.
All engagement begins with Victoria Derrick, my business partner and wife. She handles client coordination and project intake to ensure quality fit and proper scoping.
Contact:
Use the contact form to include your company name and project details
In your email, please include:
Victoria will respond within 1-2 business days to schedule discovery call or provide next steps.
Communication: Structured async updates (email/Slack), scheduled video calls (weekly or bi-weekly depending on engagement). I don't do "hop on a quick call" - all meetings are scheduled in advance with clear agendas.
Availability: Projects are scheduled in advance. Rush fees apply for expedited timelines (typically +25%).
Location: Fully remote. I work from Oak Haven in South Carolina. You can be anywhere.
Payment terms: Net 15 for hourly/retainer work. 50% deposit for project-based work. All major payment methods accepted.
Confidentiality: All client work covered under NDA. Your business operations and technical details remain private.
Solo Practitioner, AI-Amplified: I don't hand projects off to a team — I AM the team (with Victoria handling coordination). This website you're reading? Built with Claude Code and agentic AI workflows. The systems I sell are the systems I use daily. If a project requires more resources than I can provide, I'll tell you upfront. Honest feedback, clear capacity boundaries, no bait-and-switch about who does the work.
Contact Victoria to schedule a discovery call and explore how we can work together.
This rate sheet is current as of January 2026 and subject to change. Rates are locked for existing retainer clients through their contract term.
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