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Jeff Whiteside

My Journey So Far

I’ve spent more than twenty years leading engineering across SaaS, marketplace, and regulated platforms. Along the way, I’ve learned more than I ever expected—from hard work, missteps, great teams, strong mentors, and leaders who challenged me to grow.

What follows are a few of the chapters that shaped how I lead, build teams, and think about engineering today.

  1. CommandLink

    May 2024 – June 2026

    Vice President, Software Engineering & Products

    Remote

    Scaled an engineering organization from 25 to 60+ while growing seven SaaS products. Modernized the platform, strengthened engineering practices, and introduced AI-enabled workflows that improved productivity and quality.

    Scale & Organization

    25 → 60+

    Scaled engineering and product from 25 to 60+ across seven SaaS products, supporting expanding product lines and business growth. Built distributed teams across North America, Latin America, and the Philippines while strengthening the leadership structure and operating model needed to scale.

    AI Enablement

    Engineering + Product

    Led practical AI adoption across both engineering workflows and customer-facing products. Introduced AI-assisted development and code review while building shared service capabilities to support features such as summarization, routing, content generation, and voice workflows

    Platform Modernization

    Legacy → Modern

    Modernized a legacy MVC/PHP platform toward React-based experiences, a Data API layer, and independently deployable microservices. Reduced coupling and created a more scalable foundation for new products and AI-enabled capabilities.

    What I Learned

    Scale changes the job of the leader. What works at 30 people will not work at 60, and what works at 60 will not work at 100. Operational rigor, clear standards and playbooks, strong leaders, and consistent follow-through have to be built before growth makes them urgent. The biggest lesson for me was learning to evolve my own leadership as quickly as the organization was evolving.

  2. Ritchie Bros. / Xcira

    August 2015 – May 2024

    Vice President, Software Development & Infrastructure

    Tampa, FL

    Led technology for a global, multi-industry auction platform spanning automotive, livestock, bloodstock, heavy construction, and fine art. Supported both live and timed auctions, including high-profile events such as the Elton John Estate auction, while modernizing the platform, scaling distributed teams, and navigating acquisition-driven growth.

    Marketplace & Product Scale

    Multi-Industry Platform

    Expanded a shared auction platform across automotive, livestock, bloodstock, heavy construction, and fine art. Supported live weekly auctions, timed auctions, and major global events across multiple customer segments and operating models.

    Platform Modernization

    On-Prem → AWS

    Modernized the platform from on-prem infrastructure and legacy PHP front ends toward AWS, React, and Java-based services. Built a new automotive Auction Management System to replace the legacy desktop product and supported broader platform modernization across web and backend systems.

    Organization & Scale

    15 → 30+

    Scaled the engineering organization while building teams across North America and India, managing project-based contractor partners, and maintaining delivery continuity through acquisition, distributed growth, and the shift from co-located work to remote during COVID.

    What I Learned

    Complex platforms can evolve without losing customer trust. The key is understanding which parts must remain stable, which can change, and how to sequence modernization so the business can keep operating while the technology underneath it evolves.

  3. Wolters Kluwer TeamMate

    January 2013 – August 2015

    Enterprise Agile Coach & Release Manager

    Bolivia (Remote)

    Stepped outside traditional engineering leadership to focus on how large organizations build and deliver software. Evolved SDLC using Agile practices across client-server and modern SaaS products in regulated environments.

    Delivery Improvement

    Monthly → Biweekly

    Improved release cadence from monthly to bi-weekly and increased predictability through Agile and lean flow practices.

    Quality & Compliance

    Build Quality In

    Built QA, automation, and release gates that improved quality, compliance, and audit readiness across enterprise products.

    Agile Leadership

    Enterprise Agile

    Coached teams and leaders in Agile, change management, and continuous improvement across distributed organizations.

    What I Learned

    Process change only works when people understand the why and have support to adopt new ways of working.

  4. Gearworks / Xora

    June 2004 – January 2013

    Senior Engineer, Architect, Director of Engineering

    St. Paul, MN

    Grew from senior backend Java engineer and architect into my first people-leadership role while helping build mobile workforce SaaS before smartphones were mainstream. I worked primarily on the backend services that powered location tracking, data capture, routing, alerts, and field operations, while also contributing to Java MIDP mobile development. I was later promoted to Director of Software Development, built our first offshore team in Belarus, and helped lead the company through acquisition, growth, modernization, and a zero-downtime database migration.

    Product & Technology

    Early Mobile SaaS

    Helped build an early mobile workforce SaaS platform before smartphones were mainstream. I was primarily a backend Java engineer, building services for location tracking, data capture, routing, alerts, and field operations, while also contributing to Java MIDP mobile development. The platform also supported BREW clients and was white-labeled for major wireless carriers.

    Leadership Growth

    Engineer → Director

    Progressed from key hands-on engineer and architect into Director of Software Development, taking on increasing responsibility for people, architecture, delivery, and product outcomes.

    Scale & Transformation

    Built & Modernized

    Established the company’s first offshore engineering team in Belarus, navigated acquisition and growth, and led major platform modernization and database migration work with zero downtime.

    What I Learned

    Leadership changes when the work stops being only about what you can build yourself. My transition from engineer to leader taught me that technical judgment still matters, but the bigger impact comes from building capable teams, creating trust across distance, and helping people succeed through change.

Earlier in My Career

Building the Foundation

Before moving into engineering leadership, I spent several years building enterprise, education testing, and healthcare software—and teaching Java. Those roles put me close to users, production systems, requirements, and the day-to-day realities of software engineering. They gave me the technical foundation and customer-centered mindset that still shape how I lead today.

Healthcare Technology

RxHub

Software Engineer

2001 – 2004


Built Java-based healthcare integration software connecting hospitals, clinics, pharmacies, and pharmacy benefit managers. Worked on real-time eligibility, formulary, patient history, and electronic prescribing workflows where interoperability, reliability, and accurate information mattered.


Java • Healthcare • Integrations

Teaching

Programix

Java Instructor

2000 - 2002


Taught Java programming at the community-college level while working as a software engineer. Teaching strengthened my ability to break down complex ideas, communicate clearly, and help others develop their own understanding.


Java • Teaching • Communication

Consulting & Collaboration

Coherent Solutions / HealthNexis

Software Engineer / Consultant

2000 – 2001


Worked on healthcare supply-chain software, contributing to requirements analysis, use cases, software design, and delivery. The experience reinforced the importance of understanding the business problem, collaborating across disciplines, and translating customer needs into software.


Requirements • Design • Collaboration

Testing & Assessment Technology

Thomson Prometric

Software Engineer

1998 – 2000


Built software for internet-based, high-stakes testing before cloud infrastructure was commonplace. Used a combination of UDP and HTTP to support real-time testing for exams like FAA private pilot. Gained deep insight into networks, reliability, requirements management, and the psychometrics behind testing and assessment.


Distributed Systems • Testing • Requirements

Enterprise Software

GE Capital / Cargill

Consultant – Support Engineer

1997 – 1998


My first professional software engineering role. Worked directly with Cargill grain elevator operators to understand software issues, resolve problems, and incorporate fixes back into the platform. Working in Smalltalk gave me a strong foundation in object-oriented design, patterns, and engineering practices I still use today.


Smalltalk • Customer Support • Software Design • Enterprise Patterns

The Foundation That Stayed With Me

Software engineering starts with understanding.

Those early roles taught me that strong engineering is about much more than writing code. It starts with understanding the customer, the user, the requirements, and the environment in which the software has to work.

They also gave me a foundation in software design, patterns, distributed systems, integrations, and disciplined engineering practices. Most importantly, they taught me to expect change, to learn from users and production systems, collaborate closely, and adapt the software as our understanding of the problem improves.

Education, Credentials & Research

The education, credentials, and research that helped shape how I think about technology, leadership, and continuous improvement.

Education

University of Tampa logo

University of Tampa

Master of Business Administration

Published Research

Understanding the Leadership of Remote Work - Journal of Business and Educational Leadership


University of Wisconsin–Eau Claire logo

University of Wisconsin–Eau Claire

Bachelor of Science

Computer Science & Management Information Systems

President

Association for Computing Machinery (ACM) Student Chapter

Current Credentials

Project Management Institute logo

PMI Agile Certified Practitioner

Project Management Institute

2024


Scrum Alliance logo

Certified ScrumMaster® (CSM®)

Scrum Alliance

2007 - Renewed/Current

Earlier Credentials

Amazon Web Services logo

AWS Certified Cloud Practitioner

Amazon Web Services

2022-2025


SAFe® Program Consultant (SPC)

Scaled Agile

2013


Sun Certified Java Developer

Sun Microsystems

2001