Meet the Team

Meet the Team


As seasoned political and advocacy veterans, we understand how digital fits into a broader organizational strategy.

Jason Rosenbaum

Jason Rosenbaum

Jason has led some of the largest and most sophisticated digital programs and counseled hundreds of campaigns, advocacy and trade organizations on their media decisions. For more than a decade, he has lead teams that have raised more than $200 million, produced groundbreaking digital persuasion and mobilization creative and applied the most advanced research methodologies to advertising and marketing campaigns.

Prior to founding Seward Square, Jason led Digital Advertising for Hillary Clinton’s presidential campaign. He built and oversaw a 30-person team that executed a nine figure budget, the largest political digital advertising operation in history. The team was responsible for developing content, managing and negotiating media buys, and conducting research and testing for the campaign’s fundraising acquisition, voter persuasion and supporter mobilization efforts.

Jason also led Google’s Elections and Advocacy media department, and the digital departments for the Democratic Senatorial Campaign Committee, the Democratic Congressional Campaign Committee and American Association for Justice.

Craig McKinney

Craig McKinney

Craig is a strategic, multidisciplinary creative director who specializes in developing brand packages, integrated advertising campaigns and strategic communications across print and digital media.

He recently served as digital advertising creative director for Hillary Clinton’s presidential campaign. Prior to his work for Secretary Clinton, Craig was executive creative director for the international public relations agency, Burson-Marsteller, where he completed extensive work in both the entertainment and retail industries. His former clients include Accenture, Amazon, Bank of America, Microsoft, DELL, FedEx, Ford, and NBCUniversal.

Craig has won awards for original un-scripted digital programming, integrated print and digital campaigns, and mobile app creative. He holds a Bachelors of Fine Arts degree from the University of Iowa and currently resides in Venice Beach leading Seward Square Strategy’s California operation.

Tom Walton

Tom Walton

Since working on President Obama’s 2012 re-election campaign, Tom has built and managed digital media programs for dozens of Democratic campaigns, non-profits and ballot initiatives.

He has developed and implemented hundreds of successful programs for national political party committees and statewide organizations in more than 25 states. In 2016 he was recognized with a Pollie Award for his work on the Montana Gubernatorial race.

Tom graduated from the University of Northern Iowa where he studied anthropology and international affairs.

Madeline Groves

Madeline Groves

A Massachusetts native, Madeline brings research and voter contact experience from the political and technology sectors. She developed and executed research programs for a Boston based start-up and has brought those skills to media and voter persuasion and mobilization programs.

Madeline is a graduate of Dickinson College where she studied Spanish and Political Science. She is a vocal Patriots fan and sits in Seward Square Strategy’s Washington, DC office.

Kyle Jarrett

Kyle Jarett

Kyle leads Seward Square Strategy’s Pacific Northwest operation. He brings more than a decade of experience managing digital media and fundraising programs for political and advocacy organizations, including national party committees and dozens of U.S. House and Senate candidates.

He is a graduate of the University of Utah and resides in Portland, OR.

Kara Dailey

Kara Dailey

Kara has built numerous fundraising programs at the congressional, state and national levels that have raised millions of dollars online. Her work has helped grow revenue for Senator Doug Jones, Representative John Lewis, the Congressional Hispanic Caucus, Governor Roy Cooper, and Senator Michael Bennet’s presidential campaign.

Kara is from from Virginia Beach, Virginia and sits in Seward Square’s Washington, DC office.

Philip Trevisan

Philip Trevisan

A native of New Jersey, Philip brings both field and analytic experience to Seward Square Strategies. Previously, he worked at a predictive analytics firm developing online voter interest analytics tools.

Philip is a graduate of the University of St. Andrews in Scotland, where he studied International Relations and Modern History. He also founded an organization that mobilizes Democrats in the UK to engage in American politics.