Senior Lifecycle Marketing Manager

About

is revolutionizing the $100B+ short-term rental industry. We curate every aspect of the guest experience, from our smart homes to our intuitive booking platform. Our mission is to help people find their happy place, and our vision is to create the infrastructure for people to experience the world.

Senior Lifecycle Marketing Manager

OS

Want to build the retention engine behind one of hospitality tech's fastest-growing platforms? We're looking for a Senior Lifecycle Marketing Manager to join OS and own the entire customer journey for the property managers and vacation rental operators who run their business on us. If turning raw customer data into campaigns that actually move the needle gets you fired up, let's talk.

About OS

OS is 's platform for hospitality operators: a conversion-optimized website builder, automated guest marketing, AI-powered distribution, and one-click PMS integrations, all in one place. We're already powering property management companies across the country and helping operators unlock serious direct-booking revenue, and we're just getting started.

We're a small, high-craft team that moves fast and builds things we're proud of. Our mission: build the infrastructure that makes it effortless to feel at home anywhere, for hosts and guests alike.

The Role

As our Senior Lifecycle Marketing Manager, you'll own the customer journey end to end, from the second a property manager signs up through onboarding, activation, engagement, expansion, and retention. You'll build the automated campaigns, segmentation, and messaging that turn brand-new sign-ups into engaged, loyal, long-term customers. This role is highly cross-functional and refreshingly measurable: you'll partner closely with Product, Sales, Customer Success, and Growth Marketing, and your impact will show up in the numbers that matter most: activation rate, retention, expansion revenue, and churn.

What You'll Do

• Own lifecycle marketing strategy across the full OS customer journey: onboarding, activation, engagement, retention, expansion, and win-back.
• Build, launch, and continuously optimize automated email, in-app, and SMS campaigns using our marketing automation / CRM stack.
• Segment and personalize messaging based on customer behavior, product usage, and lifecycle stage.
• Partner with Product, Sales, and Customer Success to spot key lifecycle moments and build campaigns that drive activation and crush churn.
• Run sharp A/B tests across subject lines, content, timing, and channel to keep leveling up performance.
• Build and maintain dashboards for the KPIs that matter: activation rate, retention, net revenue retention, churn, and LTV.
• Collaborate on onboarding content and in-product messaging that gets property managers hooked on the features that matter most.
• Own and evolve the lifecycle marketing tech stack, including integrations between the CRM/ESP and product data.

What We're Looking For

• 5+ years in lifecycle, CRM, or retention marketing, ideally at a B2B SaaS company.
• Hands-on chops with a marketing automation / lifecycle platform (Customer.io, Braze, Iterable, HubSpot, or similar).
• Strong analytical instincts: you're comfortable pulling and interpreting data (SQL a plus) to segment audiences and prove impact.
• A track record of building campaigns that measurably moved activation, retention, or expansion metrics.
• Excellent, persuasive writing: you craft messaging that sounds human, not robotic.
• A self-starter who thrives in a fast-moving, high-craft team.

Nice to Haves

• Experience in proptech, hospitality, travel, or vacation rentals.
• Experience marketing to SMB or mid-market operators rather than consumers.
• Familiarity with property management systems (PMS) or similar operator-facing software.

Compensation

Market rate for a Series B startup and the Senior Lifecycle Marketing Manager title. Remote (United States).

Why

Join a small, high-craft team in building genuinely category-defining hospitality technology, with real traction already (10,000+ properties, $80M+ in bookings facilitated) and a huge runway still ahead.