Resume to Retirement
Forty years is a long time to spend working. Long enough to build a career, change directions, learn a few things the hard way, meet some interesting people, and collect more than a few stories along the way. I have included all the links in chronological order of my journey and my resume. I hope you enjoy the ride.
how my working life really started
how I stumbled into a technology career
my move from warehouse work into computers
This isn’t a résumé in the traditional sense. I’m not looking for a job, trying to impress a recruiter, or polishing my credentials for the next opportunity. Those days are behind me. I’m retired now, and this is simply a record of the professional road I traveled, the work I did, and the experience I accumulated along the way.
my first job in computer operations
my move into DEC’s VMS engineering group
leaving DEC for the emerging cellular industry
my return to DEC as an independent contractor
Looking back at a career is a little like looking through an old photo album. You remember some moments clearly, wonder how others happened, and occasionally ask yourself what you were thinking. Jobs that once seemed like the most important thing in the world eventually become chapters in a much larger story. Some opened doors, some taught hard lessons, and others probably made more sense at the time than they do today.
my move from DEC to Fidelity Investments
my move from Fidelity Boston back to New Hampshire
my technical leadership role at Fidelity in Merrimack
So here it is: forty years of working life, recorded for the sake of remembering where I’ve been and what I did along the way. Not a sales pitch, not a request for a job, and certainly not a claim that I had everything figured out. Just my career history, a record of one man’s working life, and a reminder that the road from starting out to retirement is rarely a straight line.
my decision to leave technology and try running a business
what I learned from my year running Puckmasters
how an unexpected conversation opened the door to JPMorgan Chase
my interview and the start of my JPMorgan Chase career
moving to Florida without leaving my job
Resume
KEVIN WHOLLEY
Technology Operations Executive | Release & Change Management | Enterprise Governance | Production Risk Reduction | Financial Services (2T+ Transaction Systems)
EXECUTIVE SUMMARY
Technology operations executive with nearly 40 years of experience designing, building, and leading release management, change governance, and production deployment frameworks within large-scale enterprise environments.
Recognized for establishing structured release and change management processes where none existed, improving operational control, reducing production risk, and enabling coordinated technology delivery across global development, infrastructure, QA, and business organizations.
Extensive experience in financial services environments supporting mission-critical systems, including merchant services platforms processing approximately 2 trillion transactions annually.
Core expertise includes release governance, change control, deployment coordination, operational risk reduction, process design, executive reporting, and cross-functional technology alignment. Proven ability to stabilize fragmented environments and introduce scalable, repeatable operational discipline.
CORE COMPETENCIES
- Release Management Strategy & Execution
- Change Management Governance (ITIL-aligned)
- Production Deployment Coordination
- Operational Risk Identification & Mitigation
- Enterprise Process Design & Implementation
- Cross-Functional Technology Leadership
- Executive Reporting & Operational Metrics
- Global Team Coordination (Onshore / Offshore)
- Technology Operations Stabilization
- Stakeholder & Business Alignment
- Agile / Scrum / Waterfall Delivery Models
- Production Change Review & Approval Structures
TECHNICAL SKILLS
Platforms & Tools:
Jira, ServiceNow, Git, Jenkins, ClearCase, PVCS, Unix/Linux, AWS (Cloud Practitioner)
Data & Analytics:
Excel (Advanced), Google Analytics Certification
Programming & Scripting:
DCL, SQL, Shell Scripting, Python, Perl, JavaScript, C, HTML, CSS
PROFESSIONAL EXPERIENCE
JPMORGAN CHASE
Vice President – Release & Change Management, Merchant Services
2008 – 2025
Led enterprise release and change management operations supporting merchant services technology platforms processing approximately 2 trillion transactions annually across highly complex, distributed systems spanning cloud, legacy platforms, and multiple database technologies.
Managed release governance, change scheduling, deployment coordination, production risk assessment, and executive-level reporting across a global technology ecosystem involving 100+ applications and cross-functional teams.
Supervised 5 direct reports and coordinated with offshore teams in India and Singapore.
Key Contributions:
- Built and matured enterprise release and change management governance processes in a highly complex financial services environment.
- Established structured change scheduling and coordination practices that reduced production errors and improved deployment reliability.
- Introduced formal risk assessment processes for production changes and exception handling.
- Developed weekly and monthly executive reporting frameworks improving visibility into change activity and operational risk.
- Led enterprise change review meetings and cross-functional coordination across development, QA, infrastructure, and business units.
- Improved overall change efficiency and reduced production incidents through standardized governance and communication structures.
FIDELITY INVESTMENTS
Director – Release & Change Management
1996 – 2006
Directed release and change management functions supporting investment fund pricing systems and later HR/Payroll technology platforms.
Managed a team of 7 direct reports and led enterprise-wide process design and implementation initiatives.
Key Contributions:
- Designed and implemented formal release and change management processes across multiple enterprise platforms.
- Established governance documentation standards and operational release controls.
- Led implementation of ClearCase version control and defined branching strategies enabling parallel development.
- Improved coordination between development and operations teams through structured release processes.
- Enhanced deployment consistency and reduced operational ambiguity across business-critical systems.
PUCKMASTERS HOCKEY TRAINING
Owner & Operator
2006 – 2007
Founded and operated a full-service hockey training business serving 150+ clients, including facility development and program delivery.
Responsible for all aspects of business creation and operations, including facility buildout, sales, marketing, coaching programs, and client management.
Key Contributions:
- Built business from concept to full operational facility, including rink development.
- Delivered on-ice and off-ice training programs supported by coaching certification.
- Managed all sales, marketing, operations, and client acquisition activities.
- Scaled client base to 150+ athletes with a single coach structure.
DIGITAL EQUIPMENT CORPORATION
Release Coordinator (Former Computer Operations Trainee)
1986 – 1996
Entered organization through formal operations training program and transitioned into release coordination for VMS operating system environments.
Responsible for coordinating software installations and system releases across multiple hardware configurations in enterprise environments.
Key Contributions:
- Coordinated operating system deployments and production release installations.
- Supported complex multi-platform hardware and software environments.
- Developed foundational expertise in enterprise release coordination and production operations.
- Transitioned from operations training into release management responsibilities.
EDUCATION
Bachelor of Arts (BA), Psychology
Southern New Hampshire University – 2010
Associate Degree, Business
New Hampshire College (now Southern New Hampshire University)
CERTIFICATIONS
- AWS Certified Cloud Practitioner
- Google Analytics Certification
- USA Hockey Level 4 Coaching Certification
- Personal Training Certification
- ClearCase
PROFESSIONAL FOCUS (CONSULTING POSITIONING)
Available for consulting and advisory engagements focused on:
- Release and Change Management Transformation
- Production Risk Reduction & Operational Stabilization
- Deployment Governance Design
- Process Documentation & Operational Maturity Improvement
- Recovery of fragmented or inconsistent release environments
The end of the road
my decision to retire after more than 40 years of work
how my career journey brought me to retirement in Brazil
Have you followed an unexpected career path? What jobs, changes, or experiences shaped the person you became? Share your story in the comments.
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