The Company
Stakeholders VR is building the best vacation rental company in the world. We launched May 1, 2026 by acquiring 18 property management brands across five regions, resulting in roughly 4,700 homes under management and about one million guest stays a year. We support the entrepreneurial operators and communities that manage some of the most valuable assets their owners will ever hold.
Our model combines local expertise with the scale and efficiency of a national operation. Local brands keep their identity. Founders stay as equity partners. Our Mission Control team builds the technology, tools, and shared infrastructure that independent operators cannot build alone. A shared AI service layer will improve revenue, marketing, finance, and operations across the full portfolio, all in service of world-class hospitality for our guests.
The executive team includes veterans from ResortQuest, Compass, Bridgewater, Overmoon, Wheelhouse, Inhabitat, Grand Welcome, and Lerer Hippeau.
If you want to build a defining brand in travel and hospitality, back the entrepreneurs who make it run, and use AI to power the whole thing, come build with us.
The Role
This is a player-coach seat with massive impact potential. You sell owners directly and develop ways to bring in more pipeline (realtor referral networks etc) while you build, manage, and mentor the team that sells alongside you. You own the function end to end and report to the CMO.
You start by managing your first team member and writing the plan to grow the team from there. The shape of that team is yours to design as the portfolio scales, including the move toward regional sellers working their own regional markets over time.
Mentorship here runs on two levels. There is the team you hire and grow directly. And there are growth-minded people already sitting inside the PMCs in the field, who have the instinct for this work and need someone to develop it. You do both.
You will also read the portfolio like an operator. You analyze each PMC's owner-acquisition motion, find where the upside is, and put effort and resources against the highest-impact areas rather than spreading them evenly.
What You'll Own
- The owner-acquisition motion across the portfolio. You run the outreach, the relationships, the agreements, and the follow-through after onboarding. Selling and handoff/partnership with the PM teams is critical to build a well rounded growth motion to reduces churn.
- Lead Generation. You partner with the CMO and marketing team to contribute to the strategy of lead generation, referrals, and partnerships that feed the pipeline.
- A voice in M&A. As we look at new PMCs, you assess each target's owner motion, channel mix, and growth upside. Once a deal closes, you own owner-growth integration, and every onboarding sets the standard for the next one.
- Owner retention and loyalty across the portfolio. Churn is a big contributor of EBITDA loss across the portfolio and you will have a stake in helping to reduce this number. Every owner we retain compounds over time and builds positive word of mouth for future pipeline.
- The growth tech stack. You will partner with the marketing and M&A team on the technology to run the team. We leverage HubSpot today with plans to build a custom AI CRM in 2026. The ESP, attribution, lead routing, and the rest of the stack are decisions we make together.
- An AI-native motion from day one. We are building this way from the start, not bolting it on later. Your daily workflow and team planning assumes AI is part of how you operate the department.
Who We Are Looking For
- An operator ready to own a function. You have led people and run a pipeline yourself, and you are ready to step fully into leadership. This is real ownership of a function from the ground up, and we are looking for someone who is excited to build from the ground up and knows how a world class sales team operates.
- Pattern recognition for multi-brand or franchise worlds. The strongest backgrounds come from real estate, hospitality, marketplaces, or vertical software with distributed operators. Connection to the realtor community is especially relevant, given how large an impact a successful agent referral program can have on the owner pipeline.
- A network you can hire from. The best person here brings a bench of strong BD talent around the country and can recruit their own team, not just run their own pipeline. As we move toward regional selling, that network becomes how we staff it.
- Inside sales and BD muscle. You have carried a number and managed others carrying theirs. You understand comp design, ramp curves, and pipeline math from having lived them.
- AI fluency in practice, not in theory. You have shipped real programs that lean on tools like Claude, ChatGPT, Clay, HubSpot, and Gong, and you can tell the difference between a useful workflow and a demo.
- Comfortable in a PE rhythm. Board reporting, tranche timelines, and EBITDA accountability are part of the work, not friction to manage around.
Compensation
Compensation is competitive with senior growth roles at early-stage companies: a competitive base plus a commission structure, a performance bonus tied to growth metrics, and potential profits interest in the holding company.
- Base - Competitive, set to the level and experience you bring
- Commission - Structured against the owner-acquisition motion you run
- Bonus - Performance bonus tied to growth metrics with an EBITDA gate
- Equity - Potential profits interest in the holding company
Why Now?
The function is greenfield and the portfolio is about to grow. Whoever takes this seat sets the operating system, the stack, the team, and the culture before any of it has precedent. For the right operator, this is where you own a function for the first time and write the playbook that fuels every future acquisition.