Founder Story


I have always been drawn to the same basic question: how do things work, and how could they work better?

That question first led me to MIT, where I studied Mechanical Engineering and developed a rigorous, systems-based approach to problem solving. As an engineer and consultant, I worked on complex technical projects in fields including medical devices and biotechnology, where success depended not only on good technical work, but on clear communication between people with different expertise, priorities, and constraints.

Over time, I realized that many of the hardest problems were not purely technical; they were operational. Teams had the right people and good intentions, but their workflows were unclear. Information lived in too many places. Decisions stalled. Projects moved forward, but too slowly due to unnecessary friction.

That realization led me deeper into healthcare systems and operations. I earned a Master of Science in Healthcare Management from Northeastern University in 2023, focused on digital transformation in healthcare, and gained firsthand experience inside primary care settings. Seeing the daily realities of healthcare operations reinforced what I had already learned as an engineer: good systems matter. No matter the industry, the way work is structured directly affects the people doing the work and the people being served.

I founded Oak Root Operations to help organizations build better systems: strong, practical, and designed to last. The name reflects the kind of support I aim to provide. Oak is valued for its durability, versatility, and longevity, while roots speak to foundations that go deeper than surface-level fixes.

Every organization operates differently, but every successful organization relies on clear systems, effective communication, and intentional execution. Oak Root Operations provides customized operational support that helps businesses improve efficiency, strengthen processes, and confidently navigate growth.

Simon Wilkes

Fractional COO & Operations Leadership

Process Development & Workflow Optimization

Project Management & Service Coordination