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Reg Calcagno has a diverse range of work experience in various organizations. In 2010, they co-owned and served as the President of Lansing Derby Vixens, LLC until 2013. In 2013, they worked as the One Capital Region Campaign Lead Field Organizer at Unity Michigan, where they successfully built support for comprehensive nondiscrimination ordinances in three Lansing Area Townships.

From 2014 to 2015, Reg worked as an Associate at Badlands Strategies. In 2015, they served as the Public Education Campaign Director at Michigan for Marriage, overseeing all aspects of a statewide advocacy campaign.

Starting in 2016, Reg held multiple roles at the ACLU, including Trans Justice Campaign Advocacy and Policy Strategist until 2020, and State Advocacy Strategist until 2019. Reg developed political strategies, traveled to targeted states, built relationships, and executed tactics with local and national partners to advance state campaigns.

In 2016, they also worked as a Lead Field Manager at Freedom for All Americans, developing field and recruitment plans to decrease discrimination and increase support for nondiscrimination protections.

From 2020 to 2021, Reg worked as the Senior Director of Government Affairs at The Lesbian, Gay, Bisexual and Transgender Community Center. In 2021, they became the Regional Field Director at Freedom for All Americans.

In 2022, Reg worked as an Adjunct Faculty at Smith College School for Social Work, co-designing and teaching a graduate-level course on research methods for social change. Currently, they are the Deputy National Campaign Director at the Human Rights Campaign.

Reg Calcagno attended Skidmore College from 1999 to 2003, where they earned a Bachelor of Arts degree in Government and Women's Studies. Later, from 2005 to 2008, Reg studied at the University of Illinois Chicago School of Law, obtaining a Juris Doctor degree.