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Maxwell Chalkin has a diverse work experience spanning various industries and roles. Maxwell currently holds the position of Chief Digital Officer and Senior Project Manager at MKP Communications Inc. since March 2020. Prior to this, they were a Senior Project Manager at the same company from March 2019 to March 2020.

From 2014 to 2019, Maxwell worked at Amalgamated Bank, where they held the role of FVP, Senior Marketing Manager from August 2018 to February 2019. Before that, they were a Marketing Manager from July 2014 to July 2018.

In 2013, they worked as a Legislative Aide at Sean Garballey, State Representative. In 2012, Maxwell served as a Campaign Manager for Timothy J. Toomey, Jr., Cambridge City Councillor and State Representative.

Maxwell'swork experience also includes roles at Tufts University as Silklab - Information Coordinator from February 2010 to September 2012, Boston.com as a TNGG contributor from September 2011 to April 2012, Hablo Americano as Founder and President from August 2010 to June 2011, and Legal Sea Foods as a Server and Bartender in 2010.

Maxwell began their career at MKP Communications Inc. as an Apprentice and Freelancer from 2004 to 2011. Maxwell also worked as an English Teacher/Camp Counselor at Colegio San Javier in 2009, teaching English to students and organizing activities at a summer camp.

Maxwell Chalkin attended Tufts University from 2006 to 2010, where they obtained a Bachelor's degree in Philosophy and Spanish. Maxwell also pursued a Bachelor's degree in Spanish Language and Literature and Philosophy during their time at Tufts University.