Jonathan Watkins

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About Jonathan Watkins

Jonathan Watkins is a seasoned technology advisor with experience working with more than 150 of the nation’s leading telecom suppliers. As an advisory partner for UPSTACK, Jonathan works with business owners and C-suite executives to design and implement customized communication and collaboration solutions.

Jonathan joined UPSTACK after serving more than 20 years as a founding partner and Vice President of Digital Planet Communications, a single-source agency specializing in UCaaS, CCaaS, SD-WAN, security, and traditional voice and internet solutions.

Jonathan started his career in telecommunications with McLeod USA. After four years of selling communications to businesses, he realized there was an opportunity to provide vendor-agnostic technology consulting and joined his partners in launching Digital Planet.

Jonathan’s decades of experience working with a range of services and service providers enable him to tailor solutions to increase customer experience and shareholder value. With extensive knowledge of the ins and outs of managed service models and the importance of expert delivery and support, Jonathan and the Digital Planet team have retained many customers for more than 20 years.

Jonathan has a bachelor’s degree in marketing and speech communications from St. Cloud State University. In his spare time, he’s an avid outdoorsman, hockey fan and professional photographer with a gig for the Minnesota Hockey Magazine.


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Angie Tocco | UPSTACK Advisor

St. Paul, MN

Jonathan Watkins