Headwater Strategies, LLC was born from Dylan O’Connor’s decade of on-the-ground advocacy in Washington state. From the halls of the State Legislature in Olympia to local governments, public agencies, and communities across the state, Dylan maintains positive and productive working relationships with leaders at every level of government.
Dylan founded Headwater Strategies with a clear vision: to help organizations and leaders turn their priorities into meaningful progress. That vision is deeply shaped by his commitment to progressive issues and his belief that strong advocacy can help people live happier, healthier, safer, and more prosperous lives.
Through years of professional advocacy, coalition-building, and partnership with some of the most talented public policy leaders Washington has to offer, Headwater Strategies brings the experience, relationships, and strategic insight clients need to navigate government, influence policy, and achieve their goals.
About Dylan O'Connor
Dylan O’Connor is the founder of Headwater Strategies, LLC and brings more than a decade of experience leading advocacy efforts across Washington state and beyond. His work spans a wide range of issue areas, including public safety, labor rights, victim and survivor protections, anti-hate legislation, child care and early learning, gun violence prevention, and other policies focused on improving the lives of communities across the State.
Dylan has spearheaded legislative campaigns, built effective coalitions, and helped guide major policy efforts from concept to passage. With a strong track record in lobbying, grassroots organizing, public affairs, and strategic communications, he helps clients cut through complexity, build momentum, and influence decision-makers at every level of government.
Before entering state and local advocacy, Dylan attended music school in Los Angeles and later moved to Seattle, where he graduated from the University of Washington with a B.A. in International Relations. He began his career in the international human rights arena, supporting grassroots movements and pro-democracy efforts challenging authoritarian regimes across three continents. That early work shaped his belief in the power of organized people, clear strategy, and persistent advocacy to create meaningful change.
Dylan lives in Seattle with his wife, Kaya. They are expecting their first child in August 2026.
Why Clients Choose
This work is about more than policy wins, it is about people. It is about making communities safer, families stronger, workers more secure, and futures more possible. Headwater Strategies partners with clients who are trying to solve real problems and improve real lives, bringing not only strategy, experience, and relationships, but a deep belief in the causes we help advance.
We care about the communities behind every bill, budget request, campaign, and policy goal. That is why we approach advocacy with purpose, integrity, and urgency helping clients turn their values into action and their vision for a better world into measurable progress.