Freelance Rental Property Jobs (NOW HIRING)

Wander's mission is to help people find their happy place by building the infrastructure to experience the world: beautifully designed homes, powerful technology, and 24/7 concierge support that turn a stay into something people remember.

WanderOS is Wander's operator-facing platform: an all-in-one system that helps property managers and vacation rental operators win more direct bookings. It combines a conversion-optimized booking website, automated guest lifecycle marketing, PMS integrations (11+ platforms), and AI-powered distribution, already used by 1,000+ property management companies across 10,000+ properties and responsible for $80M+ in bookings to date. WanderOS is central to Wander's growth strategy, and this hire will own turning that traction into a video presence the category hasn't seen before.

We're looking for a Video Content Creative Director to build WanderOS's video content function from the ground up: not just make videos, but build the machine that makes videos, the format bets, the production system, the talent, and the workflow that lets the team ship consistently instead of one-off. You'll set the creative vision for how WanderOS shows up on YouTube, LinkedIn, and social, and you'll own it end to end, from concept through distribution and performance.

• Define the video content strategy for WanderOS: the formats, series, and channels worth betting on to reach property managers and operators where they actually spend time
• Build the production system: process, tooling, and cadence that lets the team go from idea to published video fast and repeatably, not as a bespoke project every time
• Own end-to-end production (scripting, shooting, directing, and editing, or managing the freelancers/contractors who do) for everything from founder-led thought leadership to product demos, customer stories, and short-form social content
• Recruit and manage a bench of editors, shooters, and other creative contractors as volume scales, setting the creative bar and reviewing their work
• Partner with product marketing and sales to turn feature launches, customer wins, and industry expertise into video that supports the full funnel, from awareness through sales enablement
• Develop a consistent visual and narrative identity for WanderOS video content, distinct from (but complementary to) Wander's consumer brand
• Own distribution strategy across YouTube, LinkedIn, and other channels, and iterate the content strategy based on what's actually driving views, engagement, and pipeline
• Stay ahead of platform and format trends (including short-form and AI-assisted production tools) and bring new formats into the mix as they prove out

• 5+ years of video content or creative direction experience, with a portfolio that shows range across formats (long-form, short-form, talking-head, product/demo content)
• Proven experience building a content function or production system from scratch, not just executing inside an existing one
• Hands-on production skills: you can shoot and edit yourself, even if the long-term plan is to build a team around you
• Experience in B2B or SaaS content is a strong plus; comfort translating a technical or operationally complex product into video that a non-technical audience wants to watch
• A clear creative point of view, paired with the discipline to tie content decisions back to what's actually performing
• Experience managing freelance or contract creative talent
• Strong collaboration skills: this role sits at the intersection of marketing, sales, and product, and needs buy-in across all three

• Experience marketing to property managers, real estate operators, or other SMB/mid-market operators
• Familiarity with the vacation rental / short-term rental or proptech industry
• Experience building a YouTube channel or LinkedIn video presence from zero
• Motion graphics, animation, or AI-assisted video production experience

Join a team building the infrastructure behind some of the most beautiful stays in the country, and the software that powers the operators behind them. This is a rare chance to build a video function from a blank page, with real product traction behind you, direct access to leadership, and full creative ownership of how WanderOS looks and sounds on screen.