JOHN C. CHAPIN

SUMMARY

I help government agencies deliver mission-critical systems at scale by building high-performing engineering teams and modernizing legacy infrastructure. I have led web application development, DevOps, and SDLC management for 25+ years across healthcare, government, academic, and financial sectors, most recently managing 10 engineers who delivered Medicare.gov's Plan Finder, supporting 3.2M enrollments annually, 2.2M within the Annual Enrollment Period (Open Enrollment) with near-zero downtime. I drive technical strategy, team growth, and AI-assisted modernization on production systems serving millions of users across four federal agencies.

EXPERIENCE

Ad Hoc LLC – Senior Manager of Engineering – Philadelphia, PA (Remote)

Sep 2022 – Present (Promoted from Engineering Manager in February 2026)

• Lead a team of 10 engineers building Medicare.gov's Medicare Plan Finder, accountable for delivery, reliability, and security of the Medicare Coverage Tools (MCT) program, a compliance-heavy, national-scale system processing 3.2M beneficiary enrollments annually.
• Delivered 2.2M Medicare Part C and Part D enrollments during Open Enrollment 2025 with 99.9%+ uptime, including rapid recovery during the AWS US-East-1 outage through graceful degradation and incident playbook execution.
• Run quarterly game days to stress-test incident response across the team, building muscle memory for high-stakes outages and maintaining engagement in a fully remote engineering culture.
• Unblocked a 2-year dependency upgrade in 11 hours using AI-assisted development (GitHub Copilot), applying a compatibility-first strategy with code review and test coverage to de-risk.
• Automated CI/CD reliability analysis using Gemini and Claude APIs, cutting monthly effort by 75% (4 hours → 1 hour) and surfacing failure patterns to prioritize technical debt reduction.
• Led team training and prototyping to deliver Medicare.gov's first Provider Network discovery tool, evaluating FHIR APIs and data sources to de-risk scope before establishing external partnerships with CMS and health plans.
• Oversee modernization of MCT frontend and backend components to improve developer experience and security posture, addressing software rot and patching vulnerabilities rapidly.

Ad Hoc LLC – Staff Software Engineer – Philadelphia, PA (Remote)

Dec 2021 – Sep 2022

• Managed a team of five engineers within a multidisciplinary team of twelve and led sprint planning, biweekly practice management meetings, and agile ceremonies.
• Coordinated with 6+ VA platform teams to onboard their products and authored plugin development documentation, enabling engineers across the organization to extend Console UI.
• Improved team practices with GitHub and ZenHub; wrote RFCs and ADRs; and reported progress to platform teams, the product owner, and the Platform Crew Lead in the VA CTO’s Office.

Capital Technology Services – Software Development Consultant and Virtual CTO – Nashville, TN, and Philadelphia, PA

2014 – 2021

• Served as Lead Architect and CTO for a fintech startup delivering BSA/AML compliance data to financial institutions, including 3 of the top 5 U.S. asset managers. (Ruby on Rails, PostgreSQL, Heroku, AWS, GCP)
• Led development for Milligram Inc., a prescription pricing startup. (Rails, PostgreSQL, NIH NLM API)
• Built e-commerce tools for a medical retailer, integrated FedEx and Sage ERP. (Spree, Rails, AWS)
• Developed the front end for a top National Park Service site. (AngularJS, .NET SOAP web services)
• Developed sites for the University of Pennsylvania Carey Law School, and research software for neuroscience and autism studies at the University of Pennsylvania and Drexel University.

Bytes of Knowledge, Inc. – Software Development Manager – Nashville, TN

2012 – 2014

• Established Agile development practices, source control, issue tracking, and CI/CD pipelines across 100 projects and 8,000+ issues, standardizing delivery processes across the organization.
• Scaled the development team from 3 to 16 engineers in 2 years while managing delivery for clients including Peabody College, Logan's Roadhouse, Zander Insurance, and Caterpillar Financial.

Robert Half Technology – Consultant

2011 – 2012

• Developed Android, iPhone, and iPad applications for clients including Firestone Tire and Rubber Company.

Hooah Interactive Communications LLC – Senior Software Engineer – Nashville, TN

2010 – 2011

• Led delivery of a HIPAA-compliant health information exchange portal for the Army National Guard in 12 months, achieving 86% test coverage, DoD CAC authentication, and 300+ pages of documentation. (Zend Framework, PHP, SOAP)
• Contributed to the website for the $480 million Amway Center, an NBA venue, and built applications for the Army Reserve’s “Hero 2 Hired” program.

eGovernment Solutions LLC – Director of Software Development – Nashville, TN

2007 – 2009

• Led the team that built Nashville and Davidson County, TN’s first online vehicle registration system.

Base Systems, Inc. – Senior Developer – Nashville, TN

2005 – 2007

• Maintained Rails and Perl software for medical dictation and transcription on Linux, including HIPAA-compliant security.

Independent software consultant and network administrator – Nashville, TN

2003 – 2005

SKILLS

Engineering Leadership

Engineering Management, Agile, Scrum, SDLC, Budget Control, Technical Direction, Hiring & Team Building, Incident Response, RFC and ADR Practice

Cloud & DevOps

AWS, GCP, Heroku, CI/CD, Git, Infrastructure Reliability, Security Posture Management

Compliance & Standards

HIPAA, FHIR, BSA/AML, DoD CAC Auth, SOAP and REST Web Services

Development & Frameworks

Ruby on Rails, JavaScript, PHP, PostgreSQL, Zend Framework, AngularJS

AI-Assisted Engineering

GitHub Copilot, Claude API, Gemini API, Model Context Protocol, Agent Skills

EDUCATION AND CERTIFICATIONS

Bachelor of Engineering in Mechanical Engineering
Vanderbilt University, 2003

Certifications: Anthropic Claude API Suite (2026); Leading Teams: Developing as a Leader, University of Illinois Urbana-Champaign (2025)

VOLUNTEERING AND ADDITIONAL

• Code for Nashville: Established Nashville's Code for America brigade and grew it from 0 to 650 members in the first year.
• Nashville Software School and Vanderbilt Engineering Alumni Council: Mentored students and interviewed applicants.
• Private Pilot Certificate: Airplane Single Engine Land, Instrument Rated.