Keenan has spent his career as an enterprise software operator across many GTM functions. Most notably, he was part of the founding team at data analytics company Looker, where he spent 9 years building GTM strategy and teams. Looker was acquired by Google in 2020 for $2.6B.

Before joining K5 in 2023, Keenan founded Tokyo Black, an early-stage investment adviser. Tokyo Black made 80 investments across three funds. Keenan graduated from San Diego State University.