The Team

Josh Gillespie

Chief Executive Consigliere

18 years in enterprise B2B sales. Spent a decade at PandaDoc as the top individual revenue producer, helping scale the company from $0 to $92M ARR. Over $25M in lifetime ARR closed personally, with an additional $5M as Director of Enterprise Sales.

Based in San Francisco, Josh advises early-stage startup founders on go-to-market strategy, AI-native sales infrastructure, and go-to-network execution—partnering with them from first customer to first million in ARR.

His practice operates at the intersection of high-touch selling and AI-augmented GTM—helping founders codify their competitive advantage into systems that scale without premature headcount.

Zen Lenon

Chief Revenue Consigliere

Over $350M in influenced revenue across enterprise and mid-market sales. The first representative to close $1M at Yelp, where she ranked #1 among 900 worldwide reps for four consecutive years. Subsequently scaled enterprise partnerships at PandaDoc and served as the first Account Executive hired at Lokalise in the US, achieving 200–416% quota attainment.

Currently serves as Strategic Merchant Lead at DoorDash, maintaining 206–392% quarterly attainment. Clients and partners include HBO Max, GoPro, Toyota, Amgen, Lucid Motors, and the Washington Post.

Michael Cortez

Chief Strategy Consigliere

A rare combination of enterprise sales leadership, cybersecurity domain expertise, and legal acumen. UCLA graduate with a JD from Loyola Law School and an active California bar license. Built a distinguished career selling complex security solutions at CrowdStrike, AlienVault, Proficio, and Verizon Business.

Previously held enterprise analytics roles at ThoughtSpot prior to its unicorn valuation and led sales and business development at Sequoia-backed Prismo Systems. San Francisco native.