Founding GTM Lead at Wayline

We're building the AI-powered resolution layer for property management, automating communications across voice, chat, SMS, and email for an industry that manages over 40 million rental units in the U.S. Wayline is backed by Y Combinator and top-tier venture investors with a large seed round to fuel growth. The founding team are experienced proptech operators who previously led teams at WeWork and WeLive, and bring deep knowledge of how property management companies actually operate. We're looking for a founding GTM Lead to own every channel that puts Wayline in front of the right property management companies. This is not a narrow demand-gen or SDR-manager role. You'll build our entire go-to-market engine from outbound and content to partnerships and events, working directly with the CEO. You should be the kind of person who has already built sequences with AI, automated research workflows, and used LLMs to move faster than a team twice your size. Have 5 to 10 years of experience in B2B GTM, growth, or demand generation, ideally at a seed-to-Series B startup where you built the function rather than inheriting it Have some experience, interest, or exposure to property management, pr