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Jamie Hodge Chaplin began their career in 2003 as a Housekeeper at Northern Colorado Medical Hospital. Jamie then worked as a Manager and Bartender at Kenny's Steakhouse from 2004 to 2005. After that, they served as a Server at Rock Bottom Brewery from 2005 to 2008.

In 2008, Jamie joined MercuryFit as a Representative for the Company Wellness Committee and worked there until 2012. Jamie also held multiple roles at Vantiv Integrated Payments (formerly Mercury) from 2008 to 2016, including Sales Executive, Business Development/Partner Development, Merchant Sales Executive, and Sales Operations Trainer.

Jamie later worked as an Integrated Solutions Specialist at CardConnect in 2017 and as a Channel Solutions Engineer at Vantiv Integrated Payments from 2017 to 2018. From 2018 to 2020, Jamie was the Leader of Partnership Development at Worldpay from FIS.

Currently, Jamie is employed at Olo. Jamie started in 2020 as a Regional Business Manager and now serves as the Director of Sales Engineering for Olo Pay, where they collaborate with various teams to deliver comprehensive solutions to clients and streamline sales processes.

Jamie Hodge Chaplin attended the University of Northern Colorado from 2002 to 2007, where they obtained both a BA and a BS degree in Criminal Justice. In May 2023, Jamie obtained a certification in MEDDPICC by SalesHood from an institution called olo.