William W. Chapman II (Bill)

Buffalo, NY

US Citizen | Veteran | Security Clearance: TS Eligible (Tier 5)

LinkedIn GitHub

Professional Summary

Transformational engineering leader who has built, scaled, and led multidisciplinary teams across software engineering, data science, and technical program management. Expert in managing large, globally distributed engineering teams and guiding executives through digital transformation across startups, Fortune 1000 consultancies, and large federal agencies.

I have steered organizations through every major paradigm shift in modern computing, from web-based startups and the transition to mobile, to the migration from bare-metal to cloud-native containerized platforms. Most recently, I have led technical strategy for large-scale government institutions, architecting the delivery patterns required to integrate AI into mission-critical public services.

As a hands-on technologist, I bring deep experience with AI and machine learning, including extensive use of large language models such as Claude and Copilot, deploying and embedding local LLMs, building custom agents, and enhancing agentic workflows with MCP and RAG implementations. I have helped expand adoption of AI tools across product, engineering, and design teams while maintaining the infrastructure layer, including GPU servers, to support these capabilities.

As a consulting engineer for significant portions of my career, I bring deep domain expertise across banking and finance, healthcare, automotive manufacturing, and retail services.

As a technical product owner across multiple startups I co-founded and within large organizations, I have extensive experience bringing MVPs to market, iterating on product-market fit, and maintaining complex day-two technology stacks. Product ownership has been a thread through nearly every role in my career, giving me a rare perspective that bridges engineering execution with business strategy.

Professional Experience

US Department of Veterans Affairs

Director of Engineering (Supervisory IT Program Manager) Jan 2024 – Present
  • Provide technical servant leadership for 50+ cross-functional product lines comprising thousands of engineers building and maintaining the services behind VA.gov.
  • Championed adoption of AI and agentic workflows across the agency, leading workshops and guiding developers, product owners, and designers through this paradigm shift.
  • Own engineering excellence for the VA's digital front door, setting standards, practices, and quality bars across all teams.
  • Drive engineering vision and software delivery excellence for the VA.gov Platform, the foundation for all Veteran-facing digital services.
  • Serve as Acting CTO as necessary, engaging with technical concerns from line-level engineering to senior executive leadership.
  • Mentor teams to deliver through measurement and goal-setting with frameworks like OKR and DORA.

The White House: US Digital Service

Digital Service Expert April 2022 – Jan 2024
  • Led Platform Services and Site Reliability Engineering (SRE) for the Department of Veterans Affairs, establishing guidelines for incident management, customer support, and golden signal tracking.
  • Oversaw a live migration of the entire VA.gov platform from legacy VMs to containerized services with zero downtime for millions of Veterans.
  • Served as Engineering Advisor for the "Facing Financial Shock" discovery sprint to improve cross-agency federal data sharing.
  • Built a data exploration tool as a Data Scientist to assist states in allocating funding using Census and ACS data.
  • Consulted with government executives and Congress on major public policies and technical legislation including Cloud Services and AI Policy.
  • Shaped the technical hiring and talent acquisition strategy for the Executive Office of the President.

Independent Health (via 28 Protons LLC)

Enterprise Solutions Architect July 2020 – April 2022
  • Led technical migration to Adobe Experience Manager, modernizing the organization's digital customer engagement.
  • Designed and delivered a distributed event-driven system for real-time membership tracking.
  • Drove legacy modernization by migrating mainframe workloads onto OpenShift container platforms.
  • Architected identity management solutions and HL7 FHIR integrations to meet federal healthcare interoperability regulations.

Stark & Wayne LLC (Acquired by Qarik Group)

VP of Engineering Jan 2018 – Jan 2020
  • Led a globally distributed cloud consultancy of programmers, architects, and SREs.
  • Managed and mentored a team of technical directors responsible for delivery across the firm's major portfolios.
  • Led technical engagements with C-suite executives and key stakeholders at Fortune 2000 clients.
  • Drove the sales engineering function, providing technical strategy and solution design to close enterprise deals.

Stark & Wayne LLC

Director of Engineering Jan 2016 – Jan 2018
  • Provided strategic planning and architectural direction to executive management across the Global Fortune 2000.
  • Managed a portfolio of large-scale platform engineering and digital transformation engagements.
  • Led Platform Dojos as a primary partner of Pivotal (acquired by VMware), teaching Agile methods and guiding enterprise clients through cloud and platform adoption.
  • Trained and mentored Platform, Cloud, Site Reliability, and DevOps Engineers.

Stark & Wayne LLC

Platform and Infrastructure Architect March 2014 – Jan 2016
  • Designed a chaos engineering resiliency framework to test infrastructure and containerized services at scale for a major European telecommunications firm.
  • Consulted across the Fortune 500 with organizations adopting cloud and platform technologies.
  • Built and automated a cloud/platform hardware lab environment for infrastructure automation (PXE Boot, OpenStack, iDRAC).

Risk Watch Systems

Fractional CTO Sep 2012 – May 2017
  • Provided hands-on technical implementation and executive advisement to modernize a 30-year-old desktop application into a cloud-based SaaS platform.
  • Architected and delivered the migration of the primary product onto web and mobile platforms for lifecycle tracking and compliance management of medical and lifesaving equipment.
  • Designed machine learning solutions to predict equipment failure and analyze regulatory compliance across managed device fleets.
  • Guided executive leadership through cloud and mobile computing strategy, driving the successful transition from legacy architecture to a modern, scalable delivery model.

Liaison International

Software Development Manager / Architect Aug 2009 – Sept 2013
  • Built a high-performing DevOps and application development team from the ground up, contributing to a successful acquisition by Warburg Pincus.
  • Served as primary architect for WebAdmit, the company's flagship SaaS product.
  • Designed and scaled the platform to support tens of thousands of applicants using real-time ETL and data warehousing.

Division By Zero LLC

Consultant / Partner July 2007 – Jan 2016
  • Co-founded a consultancy specializing in web and server technologies, web application development and deployment, legacy integration, and general technical consulting.
  • Planned, implemented, and developed projects spanning a wide array of industries for domestic and international clients.
  • Managed data center infrastructure including racking, SAN storage, PXE boot provisioning, and hardware redundancy across 8 racks.

Engine Yard Inc.

Application Deployment Engineer April 2008 – Sept 2009
  • Maintained daily technical interaction with startups worldwide, deploying, maintaining, and scaling applications primarily on the Ruby on Rails stack.
  • Served as the first consultant many clients interacted with; responsible for initial deployment and application scaling for businesses that grew to become household names.
  • Part of the first managed service for Ruby on Rails applications, working within a globally distributed team of infrastructure and application service experts.

Object Insight Inc.

Senior Software Developer Nov 2007 – May 2008
  • Brought on to help this startup reach MVP; continued the relationship post-employment via Division By Zero consulting.
  • Managed a team of remote developers, contributing architecture, management, and development efforts to the flagship project.

Surplus Stock Exchange

Partner May 2006 – Jan 2008
  • Co-founded and secured funding for a product serving the automotive manufacturing industry.
  • Architected and delivered a platform for categorization and redistribution of carbide tooling and manufacturing equipment.

Medical Records Online Inc.

Technical Co-Founder May 2002 – March 2006
  • Co-founded a company specializing in online medical records management.
  • Served as VP of Engineering, directing the delivery of the primary product.
  • Early innovator in healthcare interoperability and personal health record management.

WCTS Consulting

Owner May 2000 – May 2005
  • Founded a consultancy delivering network administration, custom software development, IT consulting, and workflow optimization to government and non-profit organizations.
  • Managed hardware infrastructure, IT operations, and technical training for clients.

Military Experience

US Marine Corps Reserves

Rifle Squad Leader / Marksmanship Instructor
  • Served as Infantry Radioman and Rifleman; demonstrated leadership and technical proficiency in high-pressure environments.

Education

  • M.A. Mathematics, SUNY Buffalo Teaching Assistant, Graduate Research Assistant, Graduate Research Scholarship
  • B.S. Mathematics, SUNY College Buffalo NSF Scholarship
  • A.S. Computer Science, Erie Community College
  • Management Certificate, SUNY Buffalo

Community Involvement

  • Advisory Board Member, PACM Buffalo State College
  • Co-Organizer, Nickel City Ruby Conference
  • Co-Founder, WNY Ruby Users Group