Randy Chong

VP of Software Engineering

Serious Development

Mar 2026 - Jul 2026 (5 months)

- Instituted technical documentation culture to mitigate knowledge silos. - Established technical architectural oversight to promote increased maintainability, scalability, and secure operations. - Built and configured AWS infrastructure to support projects in the absence of a Technical Operations Engineer on staff. - Hired additional Software Engineers and Interns to increase development capacity. - Provided technical leadership for the Software Engineering department via managing Project Managers, Engineers, and Interns across 3 teams with a total of 23 staff geographically distributed across the US, Guatemala, Brazil, Bosnia, Italy, Poland, and Ukraine.

VP of Engineering

Healthcarecom

May 2024 - Oct 2025 (1 year 6 months)

- Facilitating technical architecture discussions with constructive critical debate to achieve consensus of development approaches consisting of the best ideas voiced by many Engineers. - Mentoring Engineering Leaders through one-on-one guidance and all Engineers through performing Tech Talks, conducting Tech Talk watch parties, and moderating discussion forums. - Leading staff and stakeholders through agile transformations and agile rebirths in order to position teams to practice continuous self-improvement and maximize their ability to provide value to the business, clients, and consumers. - Downsized Core Engineering’s staff budget by 30% in 2024 Q3 and still facilitated $24+M revenue (+12% YoY) for 2024, +31% margin YoY, and 300+% in

Executive Director of Engineering

Healthcarecom

Aug 2023 - May 2024 (10 months)

- Established test automation infrastructure and expertise to transition away from manual testing. - Increased efficiency by orders of magnitude through re-architecting the CI pipeline to minimize the development feedback cycle; tightening the developer feedback loop cycle time from ~1 day to less than 2 hours. - Grew the Partner Services Engineering roster to 1 lead, 17 engineers, and 3 DevSecOps through a mix of hiring domestic FTE’s via postings & my personal network, off-shore contractors, near-shore contractors, and client-sourced contractors.

Director of Engineering

Healthcarecom

Mar 2022 - Jul 2023 (1 year 5 months)

- Boosted the performance of the Partner Services Engineering platform by driving the refactoring of poor architecture. - Grew the Partner Services Engineering roster from 1 lead and 9 engineers to 1 technical architect, 1 lead, 15 engineers, and 1 DevSecOps through a mix of hiring domestic FTE’s via postings & my personal network and expanding contractor sourcing to Latin America.

J

Director of Engineering

JAROOP

Jul 2021 - Mar 2022 (9 months)

- Reformed a disorganized underperforming engineering department by streamlining processes, executing an agile transformation, injecting engineering experience via technical architect hire, lifting infrastructure work from the developers via DevSecOps hires, hiring top talent, empowering engineers with ownership of what they build while keeping them accountable for their commitments, establishing a full-stack culture, and instituting software development industry best-practices. - Improved client relations from weekly explanations for late deliveries to all deliveries on-time and great satisfaction; providing a large contributing factor for Healthcare.com’s acquisition of Jaroop consulting in 2022 Q1.

Senior Development Manager

Worldpay

Apr 2019 - Jul 2021 (2 years 4 months)

- Owned the server farm and build pipeline utilized by 20+ teams responsible for development of a highly-available, high-volume payment processing platform that generates ~$300-million annual revenue. - Modernized the development pipeline from building a single monolithic platform to supporting the builds of many components and microservices. - Hired, mentored, and grew a scrum team of 11 engineers in addition to 5 matrixed reports.

Software Engineering Manager

Welltok Inc

Oct 2017 - Apr 2019 (1 year 7 months)

Senior Software Engineering Manager, Product Technology

Decision Resources Group

Jul 2016 - Jan 2017 (7 months)

Software Engineering Manager, UI Team

Decision Resources Group

Jun 2014 - Jun 2016 (2 years 1 month)

Software Engineer

Decision Resources Group

Aug 2009 - May 2014 (4 years 10 months)

Software Development Engineer

Courion Corporation

Feb 2007 - Jul 2009 (2 years 6 months)

Senior Application Engineer

OpenService Inc

Aug 2004 - Feb 2007 (2 years 7 months)

Contractor

LeapFrogRx Inc

Jun 2003 - Aug 2004 (1 year 3 months)

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