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Billy MacDonald has had a varied work experience, starting in 2005 as a student and Sports Media Assistant at Saint Anselm College. In 2009, they became an Account Executive and Marketing Assistant at The Discovery Communications Group, where they presented on social media panels and workshops and conducted hands-on classes for small to medium sized business owners. In 2010, they co-founded Siphon Marketing, a marketing agency that provided SEO, PPC, and website design services. In the same year, they joined HubSpot as a Manager, Customer Success, and then as a Senior Manager, Customer Success. In 2017, they achieved 101% of customer retention goal as Director of Customer Success, SMB. In 2018, they returned to Databox as Director of Customer Success. In 2020, they became the Vice President of Customer Success and Director of Sales at Databox, and Director of Support at Klaviyo.

Billy MacDonald attended Saint Anselm College from 2005 to 2009, where they earned a Bachelor of Arts in International Business. In May 2015, they obtained an Intelligent.ly Exchange Program certification from Intelligent.ly.