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
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
About Wayline
Wayline is an AI front desk assistant purpose-built for real estate to answer calls and messages 24/7. It’s like an always-on property manager that can convert leads and resolve issues better than any human, day or night. Our AI can be setup in as little as 24 hours and works seamlessly with existing phone/management software. Uniquely, our AI knowledge base is domain-specific to learn and handle the most complex real estate workflows. For property operators, Wayline instantly replaces robo-menus and call centers, while centralizing and scaling back-office teams.
