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Keenan's work experience includes serving as the Chief Executive Officer at Noted Analytics since January 2023. Keenan previously held the position of CEO/President at A Sales Growth Company, where they utilized the Gap Selling methodology to solve revenue growth challenges for B2B companies worldwide. Keenan also worked as an Author, publishing books like "Gap Selling" in December 2018 and "Not Taught" in December 2015.

In addition to their executive roles, Keenan has a background in the ski industry, having worked as a Ski Instructor at Vail Resorts from an unknown start date until April 2019. Keenan has also contributed to Forbes as a weekly sales and revenue generation writer from May 2014 to February 2018. Before that, Keenan served as a Mentor at TechStars from May 2010 to February 2014.

Earlier in their career, Keenan founded and served as the CEO of Socially Booked from March 2010 to August 2011. Keenan also held the position of Vice President Sales Strategy and Operations at 2Wire from March 2010 to February 2011, and Vice President/Regional Sales Leader Emerging Service Providers at Avaya from August 2007 to March 2010.

Keenan's education history begins with attending The University of Chicago Booth School of Business from 2005 to 2006, where they pursued a degree in Management (CMI). Prior to that, they completed their Bachelor of Arts in Political Science at the University of Colorado Boulder, from 1992 to 1995.

Before their university education, Keenan attended Dennis Yarmouth H.S., though specific dates and degrees obtained are not provided in the given information.

In addition to their formal education, Keenan also holds a certification as a Level 2 Instructor from PSIA - AASI Professional Ski Instructors of America - American Association of Snowboard Instructors, however, the exact month and year of obtaining this certification are not mentioned.