Note
I’m not looking for a new role at this time. As of May 2025, I will be focusing full time on writing a book.
But if you want to know what I’ve been doing…
Jessica M. Roy (Leaf)
Summary
Collaborative leader with 25+ years in tech, working at the intersection of people, process, and technology. Passionate about improving processes and enabling high-performing teams by drawing from Agile, DevOps, systems thinking, Lean Development, and servant leadership practices.
Work Experience
MassMutual (Boston), 2019-2025
Application Architect, 2022-2025
Led two cross-IT, interdisciplinary working groups: the SDLC Governance Council and the Observability Working Group. Collaborating with Governance & Risk to simplify and modernize the SDLC practice and update SDLC standards and controls. Developed an implementation plan for the DevOps Observability Strategy, in partnership with Enterprise Architecture. Also co-managed AWS cloud migrations of ~20 digital web applications, working with SRE to clarify requirements and translate them into actionable steps.
- Developed an assessment tool and coordinated assessment of 50+ teams across IT to evaluate our SDLC practice. Analyzed the results and developed action plans in alignment with our strategic goals.
- Coached and mentored developers on new technology and practices, CICD, architecture, and career development.
- Established a community to connect and support developers and dev teams across divisions and tech stacks. Currently at 200+ participants, it is used multiple times per week for collaboration and information sharing.
- Built a 300+ page Confluence site sharing knowledge and tools for developers.
- Completed training for Certified Secure Software Lifecycle Professional (CSSLP) certification.
Technical Lead, 2020-2022
Technical oversight for a new customer portal, taking it from concept and empty repository, to on-time initial deployment, to production support and ongoing development. Worked with a cross-functional Agile team to clarify requirements, design, and testing needs; prioritize technical, security, and infrastructure work; and develop a resilient application architecture.
- Mentored developers and answered technical questions for teams across IT.
- Established an onboarding process for new developers.
- Created a REST API framework and peer-reviewed all front end code in GitHub.
- Created extensive technical documentation in Confluence and architecture diagrams in LucidChart.
- Integrated authentication, logging, monitoring, and observability, and evaluated third-party technology.
Full Stack Developer, 2019-2020
Developed a customer portal in React, NodeJS, and TypeScript, working with a cross-functional Agile team to clarify design, requirements, and testing needs.
- Migrated applications to Kubernetes and coached other developers through the process.
- Peer reviewed code, mentoring developers, creating documentation.
- Worked with other teams to prepare the application for initial production deployment. Deployed ahead of schedule.
- Evaluated third party products. Implemented and used logging and observability tools.
- Suggested and implemented process improvements (Git rebase, ES Lint).
- Interviewed developer candidates and represented MassMutual at recruitment activities.
MEDITECH (Westwood, MA), 2003-2019
Lead Development Programmer, 2010-2019
Developed a greenfield web application, including front end development and REST APIs; also developed complex functionality for a medication management application. Collaborated with cross-functional Agile teams to plan, clarify requirements, anticipate challenges, improve processes, and build stakeholder relationships.
- Helped three teams transition to Agile development using Scrum, Git, Subversion, and Jira.
- Conducted 200+ code reviews in Bitbucket and Crucible.
- Documented and improved processes at the group and company levels.
- Mentored other programmers and taught classes.
- Coordinated an art gallery show and taught classes as a volunteer for the art program.
Senior Programmer/Analyst, 2003-2010
Worked with customer service and development teams to debug and fix hospital pharmacy software. Developed tools to improve the code delivery process. Wrote a 300+ page internal knowledge repository. Mentored other programmers and taught classes.
RCN (formerly UltraNet; Marlborough, MA), 1996-2001
Network Engineer, 1999-2001
Technical Support Representative, 1996-1998
Education and Certification
PMI Agile Certified Practitioner (PMI-ACP) – Project Management Institute – credential ID 4067720
Master of Science in Software Development – Boston University
Certificate in Computer Science – University of Massachusetts, Boston
Certificate in UNIX and C – Worcester Polytechnic Institute
Bachelor of Arts – Wesleyan University
Speaking
Enterprise Technology Leadership Summit, Las Vegas – August 2024
“Taming the Monster: Leading Big Change as an Individual Contributor”
Tech Ladies – virtual, May 2024
“Taming the Monster: Leading Big Change as an Individual Contributor”
Inclusive Tech Hub, Boston – virtual, January 2023
“Troubleshooting While Panicking”
MassMutual, Boston – virtual (private), 2022
“Tech Stack Overview” – explaining our tech stack to new recruiters and developers