Chief Operating Officer

Chief Operating Officer

Founding Executive Team · Orlando, FL · Full-time · On-site

About Trezly

Trezly is rebuilding real estate from the infrastructure up. The industry runs on a dozen disconnected tools, one login per task, and AI bolted onto legacy systems that can't see the deal. We replaced all of it with one unified platform, a single data layer, and Otto, our proprietary conversational, voice-enabled AI running on our own dedicated NVIDIA H200 GPU clusters, hardware we own outright. One platform serves everyone in the transaction: agents, buyers, sellers, tenants, owners, hosts. Patent-pending, UX-obsessed, and built to become the operating system the entire industry runs on.

We're not iterating on real estate software. We're replacing it. This is a rare chance to build a category-defining company from the executive level.

The Role

We're hiring our Chief Operating Officer as a founding member of the executive team, reporting directly to the CEO and serving as a true second-in-command. This is one of the most consequential hires in the company's history.

Today the CEO carries product, technology, and operations at once. Your job is to own how Trezly runs, so the CEO can focus on product vision, capital, and the strategic partnerships that scale the company. You'll build the process, rhythm, and accountability that turn a fast-moving founder-led company into a disciplined, repeatable execution machine, without ever slowing it down. You'll help shape the org, the culture, and the operating foundation that a category leader is built on.

Key Responsibilities

• Own day-to-day operations, budgeting, and cross-functional execution across the entire company.
• Build and run the operating rhythm: OKRs, weekly leadership syncs, and a consistent reporting cadence.
• Oversee project management, people operations, and administrative functions in close partnership with HR.
• Partner with the CEO on hiring, org design, vendor and partner management, and long-range planning.
• Own operational KPIs and deliver clean, consistent reporting to the board and investors.
• Install the systems and accountability that keep quality and speed high as the company scales.
• Help build and lead the executive team and the culture underneath it.

Who You Are

• 8 to 15+ years of senior operating experience, including startup or scale-up environments.
• A proven builder who has taken a company from founder-led to structured, repeatable execution without losing pace.
• A real estate, proptech, or adjacent-industry background, you understand the transaction, the players, and where the industry is going.
• Comfortable as a true #2 to the CEO: high ownership, low ego, decisive under pressure.
• Strong across operations, finance and budgeting, org design, and cross-functional leadership.
• A prior COO or equivalent executive title is a strong plus.
• Driven by building something genuinely category-defining, not by holding a title.