Happy 29th work anniversary to our Managing Principal Jesse Winterowd!

Jesse joined Winterbrook Planning (known then as Winterowd Planning Services) in 1996, working as a planning technician to provide analysis and mapping support for long-range planning projects. Since then, he earned a Master of Urban and Regional Planning from Portland State University and has participated in and managed hundreds of projects for public and private clients. He has become a trusted leader, guiding long-range planning efforts, complex entitlements, and public engagement processes across Oregon. As an American Institute of Certified Planners (AICP) planner with Project Management Professional (PMP) certification, Jesse brings technical skill, project management, and collaborative leadership to every project.

As Principal in Charge, Jesse oversees all the work that comes in and out of our doors, but some of the highlights from Jesse’s last year show the breadth of his expertise and the scale of Winterbrook’s impact:

DLCD Planning Support Across Oregon

Jesse led a series of DLCD-funded planning initiatives supporting cities across the state. These include land inventories and growth planning in Tangent and Rainier, Housing Production Strategies in Sweet Home and Happy Valley, a buildable lands inventory and comprehensive plan audit in Dayton, and a Housing Capacity Analysis Update in Pendleton. These projects provide analysis and direction to help communities meet housing needs, update land use policies, and align with state planning goals.

CORE3 Facility in Redmond

Jesse guided land use entitlements for the Central Oregon Ready, Responsive, Resilient (CORE3) facility near Redmond. The 300-acre site will serve as a centralized emergency services training center and disaster coordination hub. The project involved coordination among 28 partner agencies, Central Oregon Intergovernmental Council (COIC), and a project team led by SERA Architects to prepare an initial package of ten land use applications across two jurisdictions, including an urban growth boundary amendment, master development plan, and comprehensive plan text amendment. Winterbrook continues work with a project team led by Hennebery Eddy Architects to facilitate the first phase of project improvements on the site.

Columbia Memorial Hospital Expansion in Astoria

Jesse worked with the City of Astoria, ZGF, and Columbia Memorial Hospital (CMH) to facilitate a major expansion and hospital master plan. The project required evaluating a complex web of comprehensive plan, area plan, and code overlays against current and long-term hospital campus needs and resiliency objectives. The resulting comprehensive plan and development code amendment package created a clear path for hospital development now and into the future, serving the community and region. Winterbrook continues work in Astoria with CMH, ZGF and Knot Studio to facilitate hospital improvements as needed.

Beyond project work, Jesse has helped shape Winterbrook’s business operations, mentorship culture, and statewide reach.

Congrats, Jesse, and thank you for all you do!