As Winterbrook Planning approaches its 25th anniversary on June 1st, we’re proud to recognize another major milestone: Jesse Winterowd’s 30th year with the company.

Jesse began his planning career with Winterowd Planning while earning his Master of Urban and Regional Planning from Portland State University. When Winterowd Planning transitioned into Winterbrook Planning in 2001, Jesse continued helping shape the firm’s future—growing from technical analyst and project manager into Managing Principal.

Over the past three decades, Jesse has helped lead complex planning and permitting efforts for communities and clients across Oregon. His work has included long-range planning, housing initiatives, infrastructure projects, public facilities, environmental permitting, and development strategy. Along the way, he has also helped modernize Winterbrook’s operations, strengthen employee development, and expand the firm’s regional reach.

As Managing Principal, Jesse plays a leadership role across all Winterbrook Planning projects, including these recent highlights:

• • • Columbia Memorial Hospital expansion planning in Astoria, helping advance long-term healthcare resiliency and emergency preparedness for the region.
    • Winterbrook’s growing portfolio of DLCD-funded housing projects across Oregon (throughout the 2023-2025 and the ongoing 2025-2027 funding cycles), supporting communities with housing capacity analyses, development code updates, and housing production strategies.
    • The CORE3 emergency preparedness and training facility near Redmond, a multi-agency project designed to support emergency coordination and continuity of governance during major disaster events.

Jesse’s leadership, experience, and commitment to problem-solving have helped define Winterbrook Planning for decades.

As we celebrate 25 years as Winterbrook Planning, we’re grateful for Jesse’s continued dedication and the lasting impact he has had on the firm, our clients, and communities across Oregon.