About Stayd

Stayd is a collective of vacation rental brands operating across multiple markets, with a strong foothold on Florida’s Space Coast. We are building the best-in-class, operationally excellent vacation rental management platform in the United States. We run lean, automate aggressively, and are obsessed with delivering world-class guest experiences and owner returns.

The Opportunity

The Chief Revenue Officer (CRO) owns every revenue lever across seven vacation rental brands inside the Stayd collective. You will set pricing strategy, build the forecasting engine the whole company runs on, and partner tightly with accounting to turn that forecast into budgets and financials the executive team can trust. This is a high-ownership, high-visibility seat — the person in it directly drives top-line performance across the portfolio.

This role is fully remote. Work from anywhere in the U.S. We run a distributed leadership team and give you the tools and trust to operate independently.

What You’ll Own

Forecasting: Build, maintain, and continuously refine revenue forecasts at both the company (portfolio) and unit level across all seven brands.
Revenue Management Oversight: Manage and hold accountable our third-party revenue management service, setting KPIs, reviewing performance, and adjusting strategy when results slip.
Financial Partnership: Partner with the accounting team to build monthly, quarterly, and annual financials and budgets that tie directly to revenue forecasts and unit performance.
Pricing Strategy: Drive ADR, occupancy, and RevPAR performance across all brands with a unified but brand-aware pricing strategy.
Reporting & Insights: Deliver clear, data-driven revenue reporting and insights to the CEO, brand leads, and homeowners.
New Revenue Streams: Identify ancillary and upsell revenue streams (fees, add-ons, partnerships) and build the playbooks to capture them.
Cross-functional Alignment: Work with operations and marketing to make sure pricing, distribution, and demand generation are pulling in the same direction.

What We’re Looking For

Experience: 3–5 years in a CRO, Director of Revenue Management, or similar senior revenue leadership role. Hospitality, hotel, or vacation rental experience strongly preferred but not required for the right operator.
Analytical Firepower: You live in spreadsheets and dashboards. You can build a unit-level forecast from scratch and defend every assumption in it.
Tech & AI-Driven Mindset: You don’t just tolerate technology — you seek it out. You use AI to multiply your output and you look for ways to automate any recurring task rather than hiring around it.
Financial Acumen: You’ve owned P&L or revenue numbers before. You know how to partner with accounting and turn forecasts into budgets people actually hit.
Vendor & Partner Management: You can set expectations with third-party partners, hold them to performance, and replace them when they don’t deliver.
Bias for Action: You move quickly, own outcomes, and don’t need hand-holding. You’d rather build a system once than do the same task twice.
Communication: You can explain a complex revenue picture to an owner, an ops manager, and a CEO — each in the language they understand.

Bonus Points

Direct experience with PMS platforms (Streamline, Track, Guesty, Hostaway, or similar) and channel managers (Airbnb, Vrbo, Booking.com).
Experience with revenue management tools such as PriceLabs, Wheelhouse, Beyond, or similar.
Hands-on experience using AI tools (ChatGPT, Claude, automation platforms) to accelerate forecasting, reporting, or analysis.
Experience working across multiple brands or a portfolio of properties rather than a single P&L.

Compensation & Benefits

Base Salary: $110,000
Performance Bonus: Up to $50,000, tied to revenue and portfolio performance metrics set annually with the CEO
Target OTE: Up to $160,000
Ownership: Direct seat at the leadership table with the CEO; your work drives the direction of the company
Tools: We give our team the tools, AI platforms, and automation infrastructure to do the best work of their careers

30 / 60 / 90 Day Plan

The first 90 days are structured around three phases: learn the business and stand up a baseline, build the forecasting engine and tighten the vendor, then drive measurable performance and prove the model. Each phase ends with a concrete deliverable back to the CEO.

Days 0–30: Learn the Business, Stand Up the Baseline
Days 31–60: Build the Forecast Engine and Tighten the Vendor
Days 61–90: Drive Performance and Prove the Model

How Success Is Measured at Day 90

Forecast accuracy within ±5% at the portfolio level.
RevPAR up measurably on the bottom-quartile units.
3rd-party RM vendor either performing to scorecard or replaced.
At least one ancillary revenue stream live and producing.
Weekly revenue reporting fully automated — zero manual rebuild.