Miles Sisk

Political strategist and writer. Founder of Cascading Strategies, Chicago.

Miles Sisk

Miles Alexander Sisk
Founder, Cascading Strategies
Chicago, Illinois

Built by someone who has done the work.

I started Cascading Strategies in 2019 because the organizations doing the most important work usually have the least strategic support. The county board candidate running against the party chair. The nonprofit tracking bills in three states with a staff of four. The coalition trying to reach a million voters on a fraction of what a congressional campaign spends on television.

My background is field organizing, campaign management, and paid media. I've worked with candidates and organizations across the country: city council and county board races in Oregon and Wisconsin, California Assembly and congressional campaigns, and national advocacy with In This Together America and EarthX. That range taught me two things. The fundamentals of reaching people don't change with the size of the audience. And the organizations with the tightest constraints tend to produce the most disciplined work, because they can't afford to waste a dollar.

Before politics, I worked in real estate finance and property management in Portland, and spent several years writing about how cities grow with the ReUrbanist Collaborative and Plan Design Xplore. That's why some of what you'll read here is about land, infrastructure, and neighborhoods rather than elections. The two subjects are closer than they look: both are about who gets to decide what gets built, and who has to live with it.

I work directly with every client. This isn't a firm where you meet the principal once and get handed off. When you work with Cascading Strategies, you work with me, and I bring in specialists when the engagement calls for it.

I hold a degree in Political Science from the University of Oregon and live in Chicago.

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