Founding GTM Lead

About the role

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.

Responsibilities

• Own full-channel execution and have personally run outbound, content, paid, partnerships, and events rather than just managing vendors who did
• Be AI-native and actively use Claude, ChatGPT, Perplexity, AI SDR platforms, and automation tools to research, write, personalize, and ship faster
• Be 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
• Ship quickly, iterate constantly, and hold yourself accountable to pipeline numbers
• Sell 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
• Speak credibly about AI, ML, or conversational AI products
• Have an existing network in property management or multifamily real estate
• Experience with CRM and sales automation stacks like HubSpot, Apollo, Clay, Instantly, or Salesforce
• Build and run targeted outbound campaigns to property management decision-makers using AI-augmented research and multi-channel sequencing
• Position Wayline as the category leader through case studies, blog posts, LinkedIn, webinars, and industry reports
• Develop partnerships with property management associations, technology partners, and ecosystem players
• Strategy and planning for high-ROI industry events like NAA, NMHC, and local PMC meetups as well as Wayline-hosted experiences
• Enablement of sales team with collateral, competitive battlecards, and demo frameworks
• Hire and lead a lean GTM team as results compound

Requirements

• 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
• 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
• Be AI-native and actively use Claude, ChatGPT, Perplexity, AI SDR platforms, and automation tools to research, write, personalize, and ship faster
• Be 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
• Ship quickly, iterate constantly, and hold yourself accountable to pipeline numbers
• 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

Benefits

• 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
• 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

Pay

$180K - $220K

Schedule

Full-time