Founding GTM Lead

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.

You:

• 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, proptech, real estate, or adjacent vertical SaaS and are eager to go deep on the buyer, the sales cycle, and the ecosystem
• Own full-channel execution and have personally run outbound, content, paid, partnerships, and events rather than just managing vendors who did
• Are AI-native and actively use Claude, ChatGPT, Perplexity, AI SDR platforms, and automation tools to research, write, personalize, and ship faster
• Are technically fluent and comfortable with APIs, CRMs, data tools, and light scripting, whether that means setting up a Zapier flow, writing a SQL query, or evaluating a technical integration without hand-holding
• Make decisions with data, can build a funnel model in a spreadsheet, and know how to instrument attribution across channels
• Write exceptionally well, from cold emails to blog posts to board-ready GTM updates
• Think like an owner because in a 5-person company you will often be the first and only person doing something, and you thrive in that environment
• Can point to concrete results in past roles, whether that's pipeline you generated, revenue you influenced, or channels you built from zero to measurable traction
• Have real agency and don't wait to be told what to do. You identify the highest-leverage opportunity, move on it, and bring others along
• Ship quickly, iterate constantly, and hold yourself accountable to pipeline numbers

Bonus:

• Experience selling to property management companies like Greystar, Lincoln, Cushman, and mid-market operators
• Familiarity with property management platforms like AppFolio, Yardi, Buildium, and RealPage and how they integrate with third-party tools
• Background in AI, ML, or conversational AI products where you can speak credibly about how the technology works
• An existing network in property management or multifamily real estate
• Experience with CRM and sales automation stacks like HubSpot, Apollo, Clay, Instantly, or Salesforce

What You'll Work On:

• Full-funnel GTM strategy spanning outbound, inbound, content, paid, partnerships, events, and referrals
• Building and running targeted outbound campaigns to property management decision-makers using AI-augmented research and multi-channel sequencing
• Content and thought leadership that positions Wayline as the category leader through case studies, blog posts, LinkedIn, webinars, and industry reports
• Partnership development with property management associations, technology partners, and ecosystem players
• Event strategy including high-ROI industry events like NAA, NMHC, and local PMC meetups as well as Wayline-hosted experiences
• Sales enablement including collateral, competitive battlecards, and demo frameworks
• Hiring and leading a lean GTM team as results compound

Compensation:

Competitive base salary plus meaningful early-stage equity. This role includes on-target earnings tied to pipeline and revenue performance, so your upside scales directly with the results you deliver.

Our Office:

We have an awesome private office at the 44 Montgomery WeWork in San Francisco (Financial District)

We're an in-person company. We work together in the office during the week with hybrid flexibility.

About the Interview:

• 15 minute phone screen with CEO
• 1 hour GTM deep-dive where you walk us through a channel or campaign you built from scratch
• Take-home where you put together a 30-day GTM plan for Wayline
• Presentation of plan and meet the team
• Decision made within 48 hours