Winning Connections is an elections consulting firm that caters to Democratic and left-of-center politicians, organizations, and causes, primarily by organizing phone drives, patch-through calls, and robo-texting to potential voters or politicians. Winning Connections works on environmentalist policy, gaming, gun control, immigration policy, abortion advocacy, healthcare, education, and labor policy.
According to its website, Winning Connections has served three presidential nominees, 25 sitting U.S. Senators, and hundreds of Congressional, state legislative, and mayoral candidates. 
As of December 2020, Winning Connections’ non-profit clients includes over a dozen left-of-center advocacy groups and unions. These include labor unions, such as the Service Employees International Union (SEIU); the AFL-CIO; the American Federation of State, County and Municipal Employees; and the International Brotherhood of Electrical Workers. Winning Connections also consults for a number of left-of-center grantmaking organizations, including Pew Charitable Trusts and the Open Society Foundations. Winning Connections has also consulted for environmentalist groups, including the Sierra Club, the National Wildlife Federation, the Environmental Defense Fund, and the League of Conservation Voters Action Fund. 
Outside of these issue areas, Winning Connections has consulted for left-of-center nonprofit clients including Everytown for Gun Safety, the American Civil Liberties Union (ACLU), Planned Parenthood, Human Rights Campaign, and Moms Demand Action for Gun Sense. 
Winning Connections also serves corporate clients like MGM Grand and Anheuser-Busch. 
Elected Officials and Candidates
The Winning Connections website lists 36 elected officials and candidates at the local and federal levels that have received its services. All 36 are Democrats. Notable clients include former Democratic presidential candidate Hillary Clinton, former President Barack Obama, former Secretary of State John Kerry, former Vice President Al Gore, U.S. Representative Charlie Christ (D-FL), former gubernatorial candidate Tom Barrett (D-WI), U.S. Senator Cory Booker (D-NJ), U.S. Senator Tammy Baldwin (D-WI), former U.S. Senator Al Franken (D-MN), and U.S. Senator Bob Menendez (D-NJ). 
State Democratic Parties
Winning Connections has consulted with nine state-level Democratic parties and eight Democratic state caucuses. 
Winning Connections has consulted on dozens of ballot measure campaigns throughout the United States including the successful 2016 Campaign to Regulate Marijuana Like Alcohol in Maine, the successful 2018 Voters Not Politicians redistricting initiative in Michigan, the failed 2016 carbon tax initiative in Washington, the failed 2016 One Percent Sales Tax increase in Oklahoma, and the successful 2012 Gaming Expansion question in Maryland. 
Winning Connections founder and president John Jameson worked for numerous Democratic elected officials and candidates prior to founding the organization. In 1984, Jameson was the Virginia campaign director for Walter Mondale’s failed presidential campaign. In 1985, he was the campaign manager for Mary Sue Terry (D-VA)’s successful run for attorney general in Virginia. In 1986, Jameson was a campaign manager for the successful re-election of former U.S. Senator Fritz Hollings (D-SC). In 1987, he was the southern political director for former Vice President Al Gore’s first failed presidential run. From 1995-1996, Jameson was chief of staff for U.S. Representative Karen McCarthy (D-MO). 
Winning Connections vice president Mark Schauer was a U.S. Representative from Michigan from 2009-2011. In 2014, he ran for governor of Michigan against incumbent Gov. Rick Snyder (R-MI) and was defeated. In 2015, with the support of the Democratic Legislative Campaign Committee, Schauer founded Advantage 2020, which targeted Republican redistricting to try to elect a Democratic majority in state assemblies across the country. 
Special advisor Robin Winston runs the Winston/Terrel Group, a lobbying firm that supports left-of-center causes. Winston worked for the Louisville board of aldermen on behalf of then-Lieutenant Governor Frank O’Bannon (D-IN) and then worked as deputy director of his successful gubernatorial campaign in 1996. Afterward, Winston became the political director of the Democratic Party of Indiana, where he later worked as its head. In 2016, Winston co-founded ProgressiveThoughtsMatter, a nonprofit voter mobilization group which targets racial minorities. For the 2020 Democratic National Convention, Winston was selected to be a member of the rules committee.