STAYD

Chief Revenue Officer Vacation Rental Collective Space Coast, Florida (Remote)

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.

Title

Chief Revenue Officer

Company

Stayd — Vacation Rental Collective

Reports To

CEO

Location

Remote

Employment Type

Full-time, Exempt

Base Salary

$110,000

Performance Bonus

Up to $50,000 (target $160,000 OTE)

Brands Overseen

7 vacation rental brands within the Stayd collective

The Opportunity

The Chief Revenue Officer 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

Goal: By day 30, you can speak intelligently about every brand, every unit, and where the money is actually coming from.

Pull 24 months of historicals at the unit level: ADR, occupancy, RevPAR, booking lead time, channel mix, cancellation rate, fees / ancillary. Dump it into one clean dataset. This becomes the source of truth.
Meet with the 3rd-party revenue management vendor. Get their current pricing logic, rulesets, reporting cadence, and KPIs in writing. Ask them point-blank how they’d grade their last 12 months of performance per brand.
Identify the 20 highest-revenue units and the 20 worst-performing units. Understand why each is where it is.

Day 30 Deliverable: A written “State of Revenue” brief to the CEO — where each brand stands, 3–5 immediate red flags, and what you’re going to do about them.

Days 31–60: Build the Forecast Engine and Tighten the Vendor

Goal: By day 60, there’s a unit-level forecast the whole company runs on, and the 3rd-party RM vendor has clear KPIs they’re being graded against.

Build the unit-level forecast model. Portfolio rolls up from units, not top-down. Every assumption (ADR, occupancy, seasonality, booking pace) is defensible and version-controlled.
Partner with accounting to tie the forecast directly to the budget and P&L. Monthly forecast cadence. No more “revenue says one thing, finance says another.”
Give the 3rd-party RM vendor a formal scorecard: ADR vs comp set, occupancy vs market, RevPAR index, pickup pace, and revenue vs forecast per brand. Monthly review, quarterly business review. Put them on notice that underperformance means replacement.
Start a pricing audit on the bottom 20 units. Obvious wins first — min-stay rules, orphan nights, LOS discounts, fee structures, channel parity issues.
Stand up a simple weekly revenue dashboard for CEO and brand leads: pace, pickup, on-the-books vs forecast, YoY.
Start mapping ancillary revenue opportunities (early check-in fees, mid-stay cleans, pet fees, experiences / partnerships). Pick the top 2–3 to pilot in Q2.

Day 60 Deliverable: Live unit-level forecast model, weekly revenue dashboard in production, and a formal vendor scorecard delivered to the 3rd-party RM partner with KPIs and review cadence locked in.

Days 61–90: Drive Performance and Prove the Model

Goal: By day 90, the forecast is trusted, RevPAR is measurably moving, and at least one new revenue stream is live.

Lock in the forecasting cadence: monthly forecast, weekly pace review, quarterly budget reset. This is the rhythm the company runs on.
Either the 3rd-party RM vendor is hitting their scorecard or you’ve got a replacement plan in motion. Don’t let this drag — bad pricing compounds.
Launch 1–2 ancillary revenue streams across the portfolio. Measure incremental dollars per stay.
Drive a unified pricing strategy across the 7 brands — unified methodology, brand-specific execution. Kill any inconsistency in fee structures that’s hurting conversion.
Start pushing on the automation layer. Any report, reconciliation, or data pull done more than twice — automate it.

Day 90 Deliverable: Q2 / Q3 forecast with confidence intervals, vendor status and recommendation, ancillary revenue pilot results, and a 12-month revenue plan with targets per brand — presented to the CEO.

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.

Stayd Collective

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