Michigan · Remote

James Ramsey III

Technology Executive | CTO | Board Advisor

Senior technology leader with 25+ years building and scaling companies. CTO who has driven $750K+ in annual savings through automation, led enterprise cloud migrations, navigated two successful acquisitions, and served on four boards. I don't just set strategy—I execute it.

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Overview Leadership Engineering DevOps Resume
25+
Years in Technology
$750K+
Annual Cost Savings Delivered
7+
Companies Founded or Led
4
Board Positions Held

About Me

I build companies and the technology that powers them. Over 25 years I've founded, scaled, and sold technology businesses—from a one-person ISP in 1996 to a 3,000-server hosting operation acquired in 2010. Today I serve as CTO for a private wellness and technology holding company, where I've driven $750K+ in annual savings through custom automation, led a full AWS cloud migration, and oversee the infrastructure behind 50+ active production websites.

Throughout my career I've built and led distributed teams across multiple time zones, managed cross-functional groups of engineers, data scientists, and operations staff, and worked at every level—from mentoring junior developers to advising boards and collaborating with C-suite executives. I believe great technology starts with great people, and I've made hiring, mentoring, and team culture a priority at every company I've led.

What sets me apart: I'm both the developer and the business person. I personally architect and ship the platform behind a private wellness portfolio — 30+ websites, multiple mobile apps, and a Node 24 / Fastify API — while also owning IT operations, automation strategy, and the financials that come with running a real business. Hundreds of thousands of lines of production code shipped over the years, alongside boardroom and P&L experience. Deep engineering and real business operation, in one person.

Featured Work

A handful of the things I've shipped, scaled, or sold — picked because they show how I work, not just where I worked.

  1. GRO Networking Platform

    Board Member & Lead Architect

    2025 – Present

    A full-stack platform for a professional networking organization — chapter operations, membership management, event scheduling, and revenue share. Modernizes a legacy paper-and-spreadsheet workflow into a single multi-tenant system.

    • Architected from scratch as a board-led digital transformation
    • Multi-tenant chapter model with delegated admin and revenue-share accounting
    • Mobile-first PWA so chapter leaders can run meetings from their phones
    ReactFastifyPrismaPostgreSQLStripe ConnectCapacitor / Ionic

  2. FarmFlight (Drone + ML for Agriculture)

    CTO & Board Member

    2020 – 2024

    An agtech startup using autonomous drones and computer-vision crop analysis to give growers data-driven decision support. Led R&D, owned the technical roadmap, and ran startup operations from HR through fundraising.

    • Shipped drone telemetry + ML crop-health analysis pipeline
    • Owned governance, fundraising strategy, and product roadmap as board member
    • Built and ran a cross-functional team of engineers and data scientists
    PythonTensorFlowComputer VisionAWSReact

  3. DJRamware → Acquired by Zoyar Inc.

    Founder & Lead Developer

    1996 – 2010 (Acquired)

    Built and grew a hosting and managed-services company from a one-person ISP in 1996 into a 3,000-VPS / 150-bare-metal operation serving global clients. Acquired by Zoyar Inc. in 2010; stayed on through integration as Senior Director of Technology.

    • Founder-to-exit story: scaled from solo to acquisition over 14 years
    • 3,000+ VPS and 150+ physical servers under management at peak
    • Integrated post-acquisition operations and stayed on as Senior Director
    LinuxKVMProxmoxVMwareBGPDatacenter Operations

Areas of Expertise

Business Systems & Automation

Stripe Billing Integration, Revenue Share Models, CRM, HR & Payroll Automation, Python Process Automation, Financial Administration

Infrastructure & IT Operations

Enterprise IT, 3,000+ VPS Management, Proxmox, VMware, Unraid, AWS Cloud Migrations, Disaster Recovery, High Availability

IT Operations & Management

Active Directory & LDAP Administration, Microsoft 365 & Google Workspace Admin, Endpoint & Patch Management, Change Management, ITIL Practices, Vendor & License Management, Help Desk Operations

Product Development & Strategy

SaaS Product Architecture, Multi-Tenant Design, MVP to Production, Agile & Scrum, Digital Transformation, User Research

Security & Email Authentication

DMARC, SPF, DKIM, BIMI, MTA-STS, JWT, TOTP/2FA, RBAC, HIPAA Compliance, PCI DSS, Rate Limiting, OWASP

Software Architecture

Scalable System Design, Event-Driven Architecture (SQS, SSE), Microservices, Config-Driven Platforms, API Gateway Patterns, Monorepo Strategies

Team Building & People Leadership

Distributed & Cross-Timezone Teams, Hiring & Talent Development, Performance Management, Executive Stakeholder Communication, Mentoring, Cross-Functional Collaboration

Career History

CTO, Private Wellness & Technology Company (Confidential)

June 2015 – Present 11 years and 1 month

As Chief Technology Officer at a private US-based wellness and technology holding company, I lead all technology — both as architect and as the hands-on developer who writes the code. The company operates a wellness portfolio of 30+ consumer websites, multiple Ionic / Angular mobile apps, and a modern Node 24 / Fastify platform API, and I personally ship the platform behind it. My automation tooling has driven $750K+ in annual savings, and I led the company-wide migration from on-prem hardware to AWS, modernizing scalability, security, and disaster recovery along the way.

Hands-On Architect & Developer: Personally architect, ship, and operate the company's wellness platform — 30+ websites, multiple mobile apps, and a Node 24 / Fastify API — combining the role of CTO with the role of working engineer who still pushes production code.
Technology Leadership & Strategy: Spearheaded the technological vision and strategy for the company, driving innovation and ensuring that technology investments align with business priorities.
Automation & Cost Savings: Led the design and development of automation tools that reduced operational costs by over $750,000 annually, optimizing business processes and improving efficiency.
IT Operations Management: Directed IT operations, overseeing the company's infrastructure, cloud services, and software systems to ensure high availability, reliability, and security.
Cross-Departmental Collaboration: Worked closely with other departments to ensure that IT solutions were tailored to meet their specific needs, enhancing productivity and delivering value across the organization.
Technology Procurement & Vendor Management: Managed relationships with external technology vendors, negotiating contracts and ensuring that all software and hardware solutions were cost-effective and aligned with company requirements.
Team Leadership & Development: Built and led a high-performing technical team, providing mentorship and fostering a collaborative environment that encouraged innovation and professional growth.
Risk Management & Compliance: Ensured compliance with data protection regulations and industry standards, managing risk through strategic planning and the implementation of robust security protocols.
Cloud Migration: Led the successful migration from physical hardware to the AWS Cloud, improving scalability, performance, and disaster recovery capabilities.
Infrastructure & System Optimization: Improved the performance, scalability, and security of internal systems and databases, enabling the company to handle increasing volumes of data and traffic without compromising reliability.

CTO, FarmFlight Inc.

August 2020 – January 2024 3 years and 5 months

As the Chief Technology Officer and a member of the Board of Directors at FarmFlight, I led the technological vision and strategic direction for a company revolutionizing agricultural practices with advanced drone systems and machine learning software. I played a key role in driving technological innovation and R&D, while also managing startup operations, including HR, payroll, and financial oversight, ensuring smooth operations during the company's growth.

Leadership & Strategy: Directed a cross-functional team of engineers, data scientists, and IT professionals, fostering a culture of innovation that drives growth and modernizes agricultural operations.
Product Innovation: Oversaw the development and deployment of software solutions that optimize farming operations and empower data-driven decision-making for clients.
Board Participation & Strategic Planning: Contributed to corporate governance, aligning technological initiatives with business goals, and driving strategy alongside fellow board members.
Startup Operations: Managed HR, payroll, and internal operations, ensuring smooth workflows during FarmFlight's early stages, optimizing team performance, and supporting financial sustainability.
Collaborative Initiatives: Built and nurtured key partnerships with industry leaders, investors, and stakeholders to expand market presence and strengthen technological capabilities.
Research & Development: Led R&D efforts to incorporate cutting-edge technologies, maintaining a competitive edge in the agtech industry.
Operational Management: Ensured the security and robustness of the technology infrastructure, supporting drone operations and data analysis for reliable service delivery.

Director and Founder - Hideout Networks

October 2012 – December 2022 10 years and 2 months

At Hideout Networks, I focused on providing seamless IT operations for professionals such as doctors and lawyers, who need reliable systems but struggle with the cost and complexity of maintaining an in-house IT team. I founded the company to offer comprehensive Managed IT Services designed to minimize downtime and optimize productivity. Through automation and efficient process management, we provided scalable, reliable, and cost-effective IT solutions that helped our clients operate at peak performance.

Leadership & Strategy: Founded and led the company's strategic vision, overseeing business development, marketing, and operations to drive growth and ensure sustainability.
Client Relationship Management: Established long-term client relationships by providing exceptional service delivery and support, ensuring client satisfaction and retention.
Industry Expertise: Worked with various industries including healthcare, law, and finance, tailoring IT solutions to meet their unique needs.
Operational Excellence: Managed day-to-day operations, including strategic oversight of IT infrastructure and technology solutions for clients.
Team Leadership: Led a team of IT professionals, fostering a collaborative environment to deliver best-in-class IT services.
Acquisition of Zoyar Inc: Led the acquisition of Zoyar Inc. in 2020, successfully integrating their technology and operations into Hideout Networks, expanding our service offerings and strengthening our market position.
Managed IT Services: Delivered comprehensive managed IT services, including proactive management of systems, networks, and infrastructure to minimize downtime and optimize productivity.
Process Automation: Focused on automation and process management, ensuring efficient workflows that allowed clients to concentrate on their core business functions.

Senior Director of Technology & Development, ZoyAR Inc.

August 2010 – August 2020 10 years

As Senior Director of Technology & Development, I led IT operations and development teams, overseeing large-scale infrastructure with more than 3,000 VPS (Virtual Private Servers) and 150+ physical servers. I managed dedicated hosting, server co-location, and 24/7 operations to ensure continuous uptime, high performance, and scalability for clients worldwide.

Leadership & Strategy: Led a cross-functional team of IT professionals, engineers, and support staff, ensuring efficient operation of complex infrastructure and technical systems.
Team Management & Training: Managed and mentored a diverse team of developers, providing training, technical expertise, and performance guidance to ensure optimal team effectiveness.
Client Support & Technical Leadership: Delivered high-level technical support for clients, troubleshooting complex system issues, and ensuring that service-level agreements (SLAs) were consistently met.
Infrastructure Management: Managed the deployment and maintenance of more than 3,000 VPS and 150+ physical servers, overseeing both dedicated hosting and server co-location services.
24/7 Operations & Uptime: Ensured continuous uptime and high-performance operations for global clients, implementing monitoring tools and proactive maintenance strategies.
System Optimization & Security: Directed the optimization of server configurations and the implementation of enhanced security protocols to ensure a secure and reliable IT environment.
Disaster Recovery & Performance: Spearheaded disaster recovery initiatives, ensuring business continuity and the stability of mission-critical applications in the event of system outages.

Founder / Lead Developer, DJRamware (Acquired by Zoyar Inc. in 2010)

March 1996 – September 2010 14 years and 6 months

Founded DJRamware in 1996, positioning the company as a leading provider of professional internet services, including web hosting, server co-location, dedicated servers, internet access, and server management. I successfully developed and expanded a diverse client base, ranging from individual end-users to small businesses and large global enterprises.

Leadership & Strategy: Founded and led the company's strategic vision, overseeing all aspects of business development, marketing, and operations to ensure growth and sustainability.
Client Relationship Management: Established long-term relationships with clients through exceptional service delivery and technical support, ensuring high customer satisfaction and retention.
Acquisition & Growth: Successfully navigated the company's acquisition by Zoyar Inc. in 2010, maintaining operational excellence and client trust throughout the transition.
Team Building & HR: Managed recruitment, training, and performance of technical staff, fostering a high-performing, client-focused team to meet the evolving demands of the business.
Financial Oversight: Directed budgeting, forecasting, and financial operations, ensuring profitability and resource allocation for sustained growth during DJRamware's expansion.
Product & Service Development: Developed and provided a diverse range of internet services, including web hosting, server co-location, and managed services, catering to both small and large-scale clients.
Infrastructure Management: Built and maintained the underlying IT infrastructure, scaling the business from a small operation to supporting large enterprise customers with high-demand server solutions.
Technical Leadership: Led the development and implementation of innovative IT solutions, including server management tools and hosting environments, optimizing performance, reliability, and security.

Director of Site Development, People Media, Inc. (A Match.com Company)

May 2007 – November 2009 2 years and 6 months

As Director of Site Development at People Media, Inc. — formed when American Capital acquired Zencon Technologies in 2007 and operated it as People Media — I led web operations across a portfolio of 25+ vertically focused online communities, primarily in the dating industry, including BlackPeopleMeet.com, SeniorPeopleMeet.com, and LoveAndSeek.com, serving more than 255,000 paid subscribers. I continued in the same role through the company's 2009 sale to Match.com, retained as a leader through both transitions.

Team Leadership & Management: Managed a team of developers with full hiring, performance, and termination authority, recruiting and developing talent across a distributed team.
Operations Leadership: Served on the operations leadership team, driving site strategy, changes, and priorities across a 25+ site portfolio serving more than 255,000 paid subscribers.
Feature Planning & Code Quality: Owned feature planning and prioritization and led code reviews to maintain quality across the web properties.
Stakeholder Collaboration: Partnered with executives and business stakeholders to translate business needs into technical direction.
Operational Accountability: Held operational accountability for uptime, incident response, capacity planning, and release decisions in a 24/7 environment.
Retained Through Acquisitions: Retained through two acquisitions — American Capital, then Match.com — as a trusted member of management.

Director of Site Development, Zencon Technologies

February 2002 – May 2007 5 years and 3 months

As Director of Site Development at Zencon Technologies, I built and led the web development function and team, establishing the technical foundation behind the company's online platforms. I was hired in 2002 and led site development through Zencon's 2007 acquisition by American Capital, which operated the business as People Media, Inc. — staying on in the same role through the transition.

Team Leadership: Led and managed a development team, with responsibility for hiring and day-to-day technical leadership.
Technical Standards & Code Quality: Led feature planning, code reviews, and technical standards for the development team.
Site Development & Operations: Owned site development and web operations across the company's online properties.
Internal Tooling: Built and maintained internal tools for site structure, content management, and third-party integrations.
Monitoring & Scalability: Established monitoring, upgrade, and capacity-planning practices as the business scaled.
Technology Stack: Worked across ColdFusion, MSSQL, JavaScript, SOAP, online payment integration, and form processing.

Board & Advisory Positions

Helping companies define technology strategy, navigate growth, and reach their next stage.

GRO Networking

Board of Directors

Jan 2025 – Present

Serving on the Board of Directors for a professional networking organization. Guiding technology strategy, platform development, and growth initiatives. Driving the digital transformation of chapter operations, membership management, and revenue systems.

FarmFlight Inc.

Board of Directors & CTO

Aug 2020 – Jan 2024

Served as a Board Member and CTO for an agricultural technology startup. Guided technology strategy, R&D direction, and product roadmap. Helped shape company governance, fundraising strategy, and market positioning while leading the engineering team building drone and machine learning solutions.

Cuemby

Advisory Board Member

Jun 2020 – Aug 2020

Advised a cloud-native platform company on infrastructure strategy, DevOps practices, and go-to-market technology positioning. Provided guidance on Kubernetes adoption and multi-cloud architecture patterns.

CionSystems

Advisory Board Member

Jun 2020 – Aug 2020

Advised an identity and access management company on product strategy, enterprise security compliance (HIPAA, PCI), and scaling IAM solutions for regulated industries.

Industry Experience

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Agriculture Technology

Drone systems, machine learning crop analysis, and data-driven farm management platforms.

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Healthcare Practices

Doctor's Offices, Physical Therapy Clinics, Pain Management Centers, Dental Practices, Chiropractic Offices, and more.

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Legal Services

Law Firms, Corporate Legal Departments

Let's Build Something Together

Collaboration creates innovation. Let's build something extraordinary together!

Get in touch (602) 962-7079