Josh Earle

Founder & operator building an AI-native B2B product: Josh co‑founded Outlit (2024) and leads the company as CEO, focusing on applying generative and historical-deal AI to automate proposal creation, pricing, and contract review to help revenue teams close better deals faster. ycombinator+1

Early-stage startup experience and accelerator track record: Josh has worked through multiple startup programs and early-stage teams (including Techstars and Y Combinator W25 with Outlit), giving him hands-on founder experience in fundraising, product iteration, and go‑to‑market for AI enterprise products. obj+1

Product design background applied to enterprise workflows: Prior to founding Outlit he worked as a product designer (listed as Product Designer at Enghouse, 2023–2024) and has ~6+ years designing SaaS products—background that informs Outlit’s product-first approach to automating deal work. linkedin+1

Ottawa roots and a move to San Francisco: Josh and his cofounder met at Carleton University and launched from Ottawa before relocating to the San Francisco Bay Area to participate in Y Combinator and scale Outlit. obj