Michigan · Remote

James Ramsey III

DevOps Engineer | Cloud Architect | Infrastructure at Scale

Infrastructure specialist who has managed 3,000+ VPS, 150+ bare-metal servers, and led enterprise AWS migrations. Currently orchestrating 50+ production sites with Ansible + GitHub Actions and running modern deployment pipelines at scale.

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Overview Leadership Engineering DevOps Resume
3,000+
Servers Managed
25+
Years in Technology
$750K+
Annual Cost Savings Delivered
50+
Active Production Websites

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. 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

Cloud & DevOps

AWS (EC2, S3, RDS, Lambda, CloudFront, SQS), Docker, Ansible Playbooks, GitHub Actions, CI/CD Pipelines, Nginx, Cloudflare

Databases & Storage

PostgreSQL, MySQL, MSSQL, Prisma Migrations, Database Indexing, Historical Integrity Patterns, Multi-Tenant Schemas

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

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

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.
IT Operations Management: Directed IT operations, overseeing the company's infrastructure, cloud services, and software systems to ensure high availability, reliability, and security.
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.
Risk Management & Compliance: Ensured compliance with data protection regulations and industry standards, managing risk through strategic planning and the implementation of robust security protocols.
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.
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.

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.

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.
Operational Excellence: Managed day-to-day operations, including strategic oversight of IT infrastructure and technology solutions for clients.
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.
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.

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.

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.
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.
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.

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.

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.
Leadership & Strategy: Founded and led the company's strategic vision, overseeing all aspects of business development, marketing, and operations to ensure growth and sustainability.
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.
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.

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.

Operational Accountability: Held operational accountability for uptime, incident response, capacity planning, and release decisions in a 24/7 environment.
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.
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.

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

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.

Operational Management: Ensured the security and robustness of the technology infrastructure, supporting drone operations and data analysis for reliable service delivery.
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.

Board & Advisory Positions

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

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.

Tools & Technologies

CI/CD & Automation

GitHub ActionsJenkinsDocker ComposeTurborepoGradlePlaywrightSeleniumCypressVitestESLintPrettierHuskylint-stagednode-cron

Cloud & Infrastructure

AWS (EC2, S3, RDS, Lambda, CloudFront, SQS, Route 53)FirebaseDockerKubernetesAnsibleNginxCloudflareDigitalOceanUnraidProxmoxPM2Let's Encrypt

Databases & ORM

PostgreSQLMySQLMSSQLRedisSQLiteMongoDBPrismaSequelizeDynamoDB

Development Tools

GitGitHubPostmanJetBrains SuiteVS CodeClaude CodeDocker DesktopPrisma StudioChrome DevToolsFigmanpmpnpmSharpPDFKitMJMLHandlebars

IT Operations & Management

Active DirectoryLDAPGroup PolicyMicrosoft 365 AdminGoogle Workspace AdminEndpoint ManagementPatch ManagementMDM (Mobile Device Management)Change ManagementITIL PracticesHelp Desk / TicketingLicense & Vendor Management

Monitoring & Observability

GrafanaPrometheusCloudWatchELK StackSentryNew RelicUptimeRobotPM2 MonitoringPinoWinston

Networking & Systems Administration

TCP/IPDNSDHCPSSHTelnetFTP/SFTPHTTP/HTTPSSMTP/IMAPSNMPVPNVLANBGPFirewall ManagementLoad BalancingpingtraceroutenetstatiptablesWiresharkDatacenter Operations

Operating Systems & Virtualization

Linux (Ubuntu, CentOS, RHEL, Debian)Windows ServerVMware ESXiProxmox VEKVMUnraid OSTrueNAS

Security & Compliance

HIPAAPCI DSSDMARCSPFDKIMMTA-STSBIMISSL/TLSJWTOAuth 2.0IAMRBACOWASPCORSHelmet.jsRate LimitingHashiCorp VaultTOTP/2FAbcryptArgon2

Let's Build Something Together

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

Get in touch (602) 962-7079