Overview
Jake McConkey serves as Chief Growth Officer at 5WPR[1][3]. McConkey's background includes experience in full-cycle sales across multiple technology sectors[2]. Previous roles include Chief Revenue Officer at Spilled Milk from October 2023 to August 2026[5], GTM Strategist at mezmRISE from June 2025 to August 2026[6], and Enterprise Account Executive positions at Toolio, Northstar, and Caroo between 2022 and 2025[8][9][10]. McConkey co-founded and served as CEO of Dripbox from 2019 to August 2026[7]. McConkey currently holds a Board Member position at Spilled Milk as of August 2026[4]. McConkey earned a Bachelor of Arts in Political Science and Government from Baldwin Wallace University between 2009 and 2013[11].
Profile introduction
CGO @ 5WPR I thrive in high-growth, ambiguous environments where speed, curiosity, and adaptability win. I’ve sold AI tools, HRTech, and consulting services—and love turning unknowns into closed-won. I have a particular affinity for leveraging relationship-management skills during complex sales cycles to give the product I'm selling the inside edge. Core Strengths: • Sales strategy | Tech stack optimization | Revenue consulting • Full-Cycle Sales | SaaS Startups | Consultative Selling • MEDDICC | Challenger Sale | Deal Structuring • Fortune 100 Clients | GTM Execution | Pipeline Development…
Career history
- Chief Growth OfficerAug 2026 to present5WPR
- Board MemberAug 2026 to presentSpilled Milk
- Chief Revenue OfficerOct 2023 to Aug 2026Spilled Milk
- GTM StrategistJun 2025 to Aug 2026mezmRISE
- Co-Founder and CEO2019 to Aug 2026Dripbox
- Enterprise Account ExecutiveMay 2024 to Apr 2025Toolio
- Enterprise Account Executive2023 to 2024Northstar
- Enterprise Account Executive2022 to 2023Caroo
Education
- Bachelor of Arts (B.A.), Political Science and Government2009 - 2013Baldwin Wallace University
This page shows public professional information only, each fact cited. Is this you? send a correction, or ask for removal within 24 hours, no questions asked.