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Jonathan Woolley has a diverse work experience spanning over several industries. Jonathan began their career in 2006 as an Event Supervisor at Richards Events, where they organized and prepared for major events. In 2009, they joined the AYSO Soccer Program as a Coach, creating practices for both beginner and experienced players and leading the team to the post-season playoffs.

In 2010, Jonathan served as a Front Office Administrator and Referee at the San Diego Indoor Soccer Centre, managing player waivers, maintaining databases, and officiating matches for various age groups.

From 2011 to 2012, they worked as a Marketing Consultant at Dominion Enterprises, acquiring new business, building customer relations, and presenting online marketing solutions to real estate agents nationwide.

Jonathan also gained experience as a High School Soccer Coach at Patrick Henry High School, where they were responsible for all aspects of the boys' JV soccer team from tryouts to games, and as a Marketing Consultant at Homes Media Solutions, where they acquired new business and presented marketing solutions to real estate agents.

In 2012, they became an Energy Services Specialist at San Diego Gas & Electric, providing energy efficiency and conservation tools to customers.

At Carling Communications, starting in 2014, Jonathan held the roles of Project Manager and eventually Project Management Lead, overseeing project timelines, coordinating workflows, and ensuring client goals were met.

Jonathan is currently employed at Heller Agency as the Senior Director of Operations, a role they assumed in August 2022. Prior to this, they served as the Director of Project Management from January 2021 to August 2022.

Jonathan Woolley earned a Bachelor's Degree in Psychology from Notre Dame de Namur University, where they attended from 2005 to 2009.