Jesse Winterowd


  • Master of Urban and Regional Planning
    Portland State University
  • Bachelor of Arts
    Wesleyan University

Professional Memberships

  • American Planning Association
  • Project Management Institute

Professional Certifications

  • AICP
  • PMP

Interesting Facts:

  • Lived in Yemen and Spain
  • Speaks Spanish
  • Traveled to 5 continents

Jesse Winterowd, AICP, PMP is Managing Principal of Winterbrook Planning. He has over 27 years of planning and project management experience and specializes in leading public and private project teams through complex land use planning and permitting processes. He has worked with dozens of cities to prepare long-range planning analyses including urban growth boundary amendments, housing needs analyses, buildable lands inventories, development code amendments, and public facilities plans. He has prepared and implemented successful permitting approaches for scores of projects in the public and private sectors, including schools, colleges, correctional facilities, utility infrastructure, commercial, medical, industrial and residential buildings. He has also provided planning oversight and direction as a contract city planner for several jurisdictions over the last 20 years.  

“I’ve always been drawn to helping others and solving problems.”

Jesse grew up with land use planning as a constant background. His childhood memories include walking the halls of the Department of Land Conservation and Development in Salem, sitting through Planning Commission hearings in Springfield, and numerous discussions of regulatory constraints and solutions. After finishing his Bachelor of Arts at Wesleyan University, he moved back to the west coast and began his planning career providing technical analysis at Winterowd Planning while pursuing and earning his Master of Urban and Regional Planning from Portland State University.

Winterowd Planning transitioned to Winterbrook Planning in 2001, providing additional mentorship and training in environmental expertise with Tim Brooks. Jesse’s breadth of experience and responsibilities continued to evolve from providing technical analysis and GIS mapping support to preparing complete conditional use, environmental review, and master planning applications, to developing comprehensive planning approaches, project management, and advanced client solutions.

In addition to continuous project work and experience, Jesse pursued and earned additional planning (AICP) and project management (PMP) certifications. He saw opportunities to improve the company business model and spearheaded several management efficiency changes, implemented additional outreach and business development, modernized employee compensation and benefits, revised hiring and training protocols, and was brought on as a Managing Principal.

In his free time, Jesse enjoys playing tennis, hiking, volunteering, and exploring with his family everything that Oregon has to offer.

Representative Projects:

Island City, OR contract planning
Jesse has worked with Island City for over 20 years, providing long-range and current planning services. Among many projects, he is most proud of providing staff guidance leading Island City to approve its first workforce housing development and help address regional housing needs.

Under Armour Headquarters
Jesse prepared permitting and analysis for a consolidated application for a comprehensive plan map amendment, zone change and Type III Design Review to allow for expansion of Under Armour Corporation’s regional northwest headquarters in Portland, OR.

Portland Water Bureau (PWB)
Jesse has worked for over a decade assisting PWB with several complex land use permitting approvals in Portland, Multnomah County, and Clackamas County for critical elements of the water system that will help ensure clean, safe, and continuing water supply to about 1 million people in the Portland Metro region.