Chief Revenue Officer
Founding Executive Team · Orlando, FL · Full-time · Hybrid (on-site temporary at onset)
Own the revenue engine for a platform rebuilding an entire industry.
Trezly is the AI-native operating system for real estate. The industry runs on a dozen disconnected tools, a different login for every step, and AI bolted onto legacy systems that never see the deal. We replaced all of it: one unified platform, a single data layer, and Otto, our proprietary conversational, voice-enabled AI running on NVIDIA H200 GPU clusters we own outright. Because we own the inference, Otto works directly with customer data for search, pricing, drafting, screening, and negotiation, with no per-token markup and no rate limits, and customer data is never sold or shared with any MLS, portal, or trade association.
One platform serves everyone in the transaction: agents, buyers, sellers, renters, owners, STR hosts, guests, property managers, and investors. Patent-pending, data-sovereign, and built to become the system the whole industry runs on. We are heading into a national launch and a multi-state rollout, and we need the executive who turns that platform into revenue.
The Role
The Chief Revenue Officer is a founding member of the executive team, reporting to the CEO, and owns the entire commercial engine end to end. You will define and execute the go-to-market strategy, build and scale the sales and revenue organization, and align marketing, sales, and customer success behind one set of growth objectives.
What makes this seat different from a typical CRO role is the surface area. Trezly monetizes across multiple revenue engines and distinct customer types on a single platform, and you own all of it:
- Resale brokerage revenue, agent-side and consumer-side
- Long-term rental and property management, serving landlords, owners, and the 100 to 500 door property manager
- Vacation rental and short-term rental, a host-acquisition wedge with guest-side monetization that competes directly with the OTAs
- Trezly Title and the affiliated-services revenue that rides the same transaction
Your job is to build a coherent revenue motion across all of these, not four disconnected ones, and to make the go-to-market machine run in concert with the platform underneath it.
What you will own:
- End-to-end revenue strategy across every line: resale, long-term rental and PM, vacation rental, and affiliated services
- The go-to-market plan for a phased, multi-state rollout across licensed markets
- Building and scaling the sales organization, sales operations, comp design, and performance frameworks
- Lead generation and demand across agent, consumer, host, owner, and property-manager segments
- Pipeline, forecasting, revenue targets, and clean board-level reporting
- Pricing and packaging, in partnership with product leadership, across all revenue engines
- Alignment of marketing, sales, and customer success around shared KPIs and retention
- Partnering with the executive team on budgeting, forecasting, and performance
- A data-informed, ethical, customer-centric growth approach consistent with Trezly's data-sovereignty commitments
Who you are
- A proven revenue leader who has built and scaled a commercial organization from an early stage, not just inherited and managed one
- Deep, hands-on go-to-market experience: you have designed and executed the strategy and carried it through to predictable, measurable revenue
- Strong across sales, sales operations, demand generation, and customer success, with the ability to align all of them behind shared targets
- Fluent in using data and analytics for forecasting, pipeline management, and decisions in a fast-moving, technology-driven environment
- Experienced building and mentoring high-performing commercial teams
- Comfortable owning multiple revenue lines and customer segments at once, rather than a single product motion
- Background in SaaS, AI-powered products, or real estate technology strongly preferred; experience in a regulated industry is a plus
- Excellent communication, negotiation, and stakeholder skills, with a track record presenting at the executive and board level
- Driven by building something genuinely category-defining, not by the title on the door
For years you have watched real estate promise to modernize and never deliver, new tools bolted onto the same broken practices, none of it solving the problem underneath. You know the industry can do better by the agents, professionals, and brokerages who run on it. This is your chance to be the one who builds it.
