John C. Derrick

John C. Derrick

Fractional CTO | The Full-Stack CTO

I bring CEO, COO, and CMO experience to the CTO chair. You hire a technologist. You get an executive team — one that cuts your costs and scales your operations.

Irmo, South Carolina | Contact Victoria

Professional Summary

Seasoned digital publishing entrepreneur with nearly two decades of experience in web development, AI integration, marketing, and SEO/AIO. Founder of multiple successful online properties including HawaiiGuide.com (one of the largest independently-owned Hawaii travel resources on the web, trusted by up to 15 million annual visitors — built entirely from South Carolina), PROnetworks Technology (serving 20+ million people globally), GuideofUS.com, and GardenandBloom.com.

I have a track record of identifying major technology shifts early: I founded my first startup (PROnetworks) to coincide with the Windows XP launch in 2001, championed responsive web design adoption in 2011 when it was still emerging, and positioned HawaiiGuide for post-pandemic "revenge travel" before that term existed. While I didn't predict the AI revolution initially, I recognized its significance immediately and pivoted my entire business model within months of ChatGPT's release. This pattern of early adoption and rapid adaptation has consistently kept my projects ahead of market trends.

Expert in building dynamic, interactive web applications with AI-powered features, agentic workflows, operational architecture, and digital marketplace strategies. I specialize in designing systems where AI agents handle repetitive cognitive tasks, freeing teams to focus on high-value work. Proven track record of building systems that allow small teams to achieve enterprise-level results through automation, strategic tooling, and cognitive scaling. At my entrepreneurial peak, I managed a global remote team of 55 people across a dozen countries.

In response to the AI revolution, I didn't just adapt my existing web properties — I also launched GroveTop Studio, a physical products business that demonstrates strategic diversification in an AI-dominated marketplace. I help clients think beyond simply "adding AI" to their current model, sometimes guiding them toward creating AI-proof revenue streams entirely.

I'm a daily practitioner of multiple AI platforms (Claude/Claude Code, ChatGPT, Gemini, Manus, and others), with hands-on understanding of each model's strengths, limitations, and optimal use cases. I don't sell AI theory — I build with these tools daily and know which one solves which problem. Additionally, I bring deep expertise in email marketing systems (200K+ subscribers built across multiple properties), affiliate marketing monetization (partnerships with CJ/Expedia, FareHarbor, and vertical-specific networks), and JavaScript-based marketing automation that actually converts.

Services I Offer

Fractional CTO — The Full-Stack CTO

Strategic technical leadership for small teams (1-10 people) navigating AI adoption, system architecture decisions, and technology roadmaps. I bring 25+ years of hands-on experience without the full-time executive overhead. Because I've held CEO, COO, and CMO roles, I don't just fix your tech stack — I fix the business problems hiding behind it. I improve your marketing tracking (CMO hat) through automation (CTO hat). I streamline your operations (COO hat) by building the right systems (CTO hat). You hire a CTO. You get an executive team.

AI Strategy & Agentic Workflow Design

Design systems where AI agents handle repetitive cognitive tasks, freeing your team to focus on high-value work. From content generation to operational automation, I help you identify where AI adds real value — and where it doesn't.

Business Process Automation

Eliminate manual bottlenecks in content production, operations, and internal workflows. I build custom automation systems that multiply productivity without adding headcount.

Legacy System Modernization

Refactor dated architectures (ExpressionEngine, early PHP, outdated CMSs) into modern, AI-integrated workflows without losing SEO equity or breaking existing functionality. I've migrated systems serving millions of users while maintaining uptime and search rankings.

Web Platform Development & Modernization

Full-stack web application development with modern front-end/backend technologies. From interactive travel platforms to e-commerce systems, I build solutions that scale.

Technical Architecture & Systems Optimization

Design operational architecture that allows small teams to achieve enterprise-level results. Strategic tooling, cognitive scaling, and infrastructure that actually works.

SEO & Content Systems Strategy

Execution-focused SEO strategy based on building platforms that serve 15M+ annual visitors. Not theory — practical systems that drive organic traffic and sustainable revenue.

Email Marketing & Automation Systems

Build and optimize email marketing systems that convert. 200K+ subscribers built across multiple properties, with expertise in segmentation, behavioral automation, JavaScript-based workflows, and AI-enhanced personalization at scale.

Affiliate Marketing & Monetization Strategy

Revenue optimization through strategic affiliate partnerships. Experience managing relationships with major networks (CJ/Expedia, FareHarbor) and vertical-specific partners. I build monetization systems that align with user experience, not disrupt it.

RAG & Custom AI Chat Systems

Build production RAG (Retrieval-Augmented Generation) implementations that understand your content and convert visitors. I've built tour concierge tools suggesting FareHarbor experiences and brand-aligned chatbots representing websites in AI responses. Experience with CustomGPT.ai and modern RAG architectures for customer service, content discovery, and monetization.

Who This Is For

  • Small businesses (1–10 employees) needing enterprise-level systems without enterprise budgets
  • Founders feeling operational or technical bottlenecks who need strategic guidance, not just execution
  • Teams overwhelmed by AI tools but unsure what's actually worth implementing vs. what's just hype
  • Businesses needing practical systems built by someone who's actually operated them at scale, not consultants selling theory

Ready to See Pricing?

View transparent pricing across all engagement tiers - from strategic advisory to custom platform builds.

View Engagement Tiers & Rates →

Core Competencies

AI Integration & Agentic Workflows
Web Application Development
Artificial Intelligence (AI) & LLMs
SEO & Content Strategy
Digital Marketing & Analytics
Email Marketing & Automation
Affiliate Marketing & Monetization
Systems Architecture
Team Leadership & Operations
Product Management
Responsive Web Design
CSS, HTML5 & Web Standards
E-Commerce & Marketplaces
Full-Stack Development

Impact & Results

23+

Years Leading HawaiiGuide

20M+

People Served via PROnetworks

15M

Annual Visitors to HawaiiGuide

3M+

DualBootPRO Downloads

200K+

Email Subscribers Built

Professional Experience

Founder / Editor-in-Chief / CTO

HawaiiGuide.com · Full-time
May 2002 - Present · 23+ years
Hawaii / South Carolina

HawaiiGuide.com (Hawaii-Guide.com) is one of the largest independently-owned Hawaii travel resources on the web, trusted by up to 15 million visitors researching their dream trip to the islands. As reported by SEMRush and SimilarWeb, our platform continues to be a leading source for those planning where to go, what to do, and where to stay across the Hawaiian Islands.

Founded in 2002 and evolving ever since, HawaiiGuide has grown from a traditional content site into a dynamic, interactive web application — designed and engineered in-house. We integrate custom-built web services, AI-powered concierge recommendations, interactive itinerary planning, and affiliate-based tour suggestions — all while remaining user-friendly and mobile-responsive. I lead the full-stack web application development, using my background in publishing, design, SEO, and modern front-end/backend technologies to continuously improve the user experience and functionality.

During the pandemic, I positioned the platform for what would become known as "revenge travel" — preparing infrastructure and content for the surge in Hawaii tourism demand before that trend had a name. This strategic positioning contributed to our record traffic growth in 2021-2023.

At the heart of HawaiiGuide is a strong commitment to mālama pono — to care for the land ('āina) and sea (kai). Our goal is to encourage thoughtful, respectful tourism while helping people make meaningful connections with the islands and their culture. For us, Hawai'i isn't just a destination — it's a relationship.

Skills: Web Application Development, Artificial Intelligence (AI), SEO, Content Strategy, Front-End Development, Digital Marketing

Director of Development / Vice President, Operations

DuBose Web Group
Jul 2010 - Aug 2014 · 4 yrs 2 mos
Columbia, South Carolina Metropolitan Area

Director of Development (Jul 2010 - Nov 2013) | VP of Operations (Nov 2013 - Aug 2014)

With a strong background of over 15 years in web development and web strategy, I joined DuBose Web Group in Columbia, SC initially as Director of Web Development, where I was responsible for setting the vision of our development team, maintaining the high quality of customer care we've become recognized for, and ensuring timely delivery of reputable products and services to our diverse array of clients. I specialized in the use of ExpressionEngine CMS.

In 2011, I was an early champion of responsive web design when the approach was still emerging in the industry. I advocated heavily for the company to adopt responsive design practices, positioning our clients ahead of the mobile-first curve that would soon dominate web development.

In November 2013, I was promoted to Vice President of Operations while continuing to handle development responsibilities. During this period, I effectively wore both hats - leading the creative team, executing the company's strategic plan and initiatives, while also providing hands-on development support to our junior developer who needed significant mentorship.

Skills: Front-End Development, ExpressionEngine CMS, Team Leadership, Web Strategy

Principal Software Engineer

DualBootPRO
Jun 2006 - Sep 2011 · 5 yrs 4 mos
Columbia, South Carolina Metropolitan Area

In late 2008, a small group of PROnetworks' team members and I set out to formally solve a new set of complications related to Microsoft's latest Windows product, Windows Vista. Our initial software project work began in mid-2006, during the height of PROnetworks success. We originally entitled our software application VistaBootPRO (VBP), but when we officially launched commercial operations in December 2008, we changed the name to DualBootPRO (DBP) to more accurately reflect the name.

VBP and DBP both were highly successful software applications where VBP would tally over 3-million free downloads prior to commercial sales beginning in 2008. The software was featured and reviewed in several technology magazines and online publications including 'PC World,' 'ZDNet,' 'PC Magazine,' 'CNet,' and even was highly recommended by Microsoft's own professionals in their 'TechNet' Magazine.

Founder

PROnetworks Technology
May 2001 - Dec 2010 · 9 yrs 8 mos
Worldwide

When 'Windows XP' was released by Microsoft in the fall of 2001, I would go on to found my first formal startup, PROnetworks Technology. From the fall of that year until the winter of 2008, I devoted the majority of my spare time outside of my day job to what remains arguably my most prominent and extensively valuable company to date. Over the course of an eight year period, the growing web site provided support-related services to at least 20 million people; that tally calculated using conservative metrics.

This global-visitor statistics was eventually confirmed using Google Analytics over a two-year window from 2006-2008, in which over 12.2 million of the aforementioned visitor total would use the site alone. At its peak in 2006, the company had a combined remote workforce of 55 total volunteers and contractors located throughout the world in over a dozen countries globally.

Director of Web Content

SCETV
Jun 2007 - Jun 2010 · 3 yrs 1 mo
Columbia, South Carolina Metropolitan Area

I was responsible for overseeing all of the web content, design, and analytic data for the agency. During my tenure, I was a leader in advocating for the agency's transition from Dreamweaver-based static development to a modern Content Management System approach. This shift modernized our web operations and significantly improved workflow efficiency across the department's 30+ websites.

Notable Achievement: Received the President's Award (Dec 2008) for outstanding contributions to the organization

Information Resource Consultant

SC Department of Transportation
May 2001 - Jun 2007 · 6 yrs 2 mos

I oversaw a portion of the Highway Maintenance Management System, which tracked resources and maintenance projects for the SCDOT. I also was the web designer for the Director of Maintenance Office.

Education

Bachelor of Science (BS), Geography

University of South Carolina
1999 - 2004

Activities and Societies: Gamma Theta Upsilon - Kappa Psi Chapter, Vice President of Geography Club, NOAA Grant Research Assistant

I also have a strong background in Computer and Civil Engineering. I originally planned to major in engineering before deciding the natural sciences were more to my liking.

Key Coursework: Internet Publishing, Web Development, GIS Systems, Digital Cartography, Remote Sensing, and Data Analysis

Licenses & Certifications

Hawaii Destination Expert

Hawaii Visitors & Convention Bureau
Issued Jul 2020

Official certification recognizing expertise in Hawaiian travel destinations and tourism

Island of Hawaii Specialist

Hawaii Visitors & Convention Bureau
Issued Jul 2020

Specialized certification for the Island of Hawaii (Big Island) tourism expertise

Eagle Scout

Boy Scouts of America
Issued Dec 1996 · Earned at Age 16

Highest rank in Boy Scouts, demonstrating leadership, service, and outdoor skills. This early achievement established a lifelong foundation of discipline and commitment to service.

President's Award

SC Educational Television (SCETV)
Issued Dec 2008

Recognition for outstanding contributions to the organization

Publications

Hana Highway - Mile by Mile

Published via HawaiiGuide.com · 8th Edition

Comprehensive guide to one of Hawaii's most scenic drives. In continuous production since 2004 and updated regularly, now in its 8th Edition.

Volunteering

Sergeant & Volunteer

Irmo Police Department Explorer Post
Community Service & Law Enforcement Training

Served as Sergeant in the Irmo Police Department Explorer Post, contributing over 100 hours per month to community service, law enforcement training, and public safety initiatives. This experience instilled lasting principles of discipline, leadership, and service to community.

Adopt a Highway

Boy Scouts of America
Environment

Participated in environmental stewardship through the Adopt a Highway program, maintaining roadway cleanliness and promoting community service

Work Philosophy & Environment

"Effectiveness is the measurement of truth."

This principle guides everything I build. My work blends high-tech innovation (AI/web development) with high-touch intentionality (thoughtful design, user experience, environmental awareness). I believe the best systems emerge from clarity of purpose and elimination of noise.

Optimized for Deep Work

I work from Oak Haven, a purpose-built small home on my 35-acre property in Irmo, South Carolina. After a strategic year of downsizing and gaining clarity, I designed this workspace specifically to eliminate distractions and maximize focus. This intentional minimalist environment enables me to deliver enterprise-scale solutions with exceptional efficiency.

The result? HawaiiGuide.com reaching 15 million annual visitors, built from rural South Carolina. PROnetworks serving 20+ million people globally with a lean, distributed team. AI-powered workflows that multiply productivity without sacrificing quality. The environment matters — and I've optimized mine for maximum output.

Grounded Innovation

My background in Geography isn't just academic — it shapes how I approach systems thinking. From GIS and data analysis to land stewardship and environmental awareness, I bring a holistic perspective to technology projects. I build solutions that are both technically sophisticated and deeply practical, because I understand that effective systems must work with reality, not against it.

Autonomy & Partnership

I'd rather work 90 hours a week for myself than 90 hours for someone else. After years of building teams and leading operations at companies like DuBose Web Group, I realized my highest value comes from entrepreneurial autonomy. I genuinely enjoy helping people solve complex problems — I just prefer doing it on my own terms, in partnership with my wife Victoria.

This philosophy shapes how I work with clients: I bring the same intensity and commitment I apply to my own ventures, but with clear boundaries and Victoria managing coordination so I can stay focused on delivering exceptional results.

Solo Practitioner, AI-Amplified

This website you're reading? I built it using Claude Code and agentic AI workflows — the same systems I teach. I don't hand projects off to a team. I don't delegate technical work to junior developers. I AM the team (with Victoria handling client coordination and project intake).

If a project requires more resources than I can personally provide, I'll tell you upfront and help you find the right partner. I don't take on work above my capacity level and pretend otherwise. Honest feedback, clear boundaries, no bait-and-switch about who's actually doing the work. When you hire me, you get me — not an account manager who farms your project out to whoever's available.

Ready to Work Together?

Whether you need a Fractional CTO, AI integration, or systems architecture, I'm here to help turn your business challenges into systematic solutions.

Victoria is my business partner and wife. She handles client coordination and project intake so I can focus on delivering exceptional results. We've built multiple successful ventures together, and she ensures every project gets the attention it deserves.

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