Remote Progressive Technology Systems Jobs in Florida

This is a remote position.

Sell2Rent is a fast-growing residential real estate platform specializing in sale-leaseback transactions. We help homeowners unlock their home equity without moving, while connecting properties with single-family rental investors. We operate in 30+ states and have closed 200+ transactions.

Technology is a key driver of our growth. We’ve built a proprietary operating platform, AI agents for lead qualification and outreach, an investor-matching layer, and a lead engine that supports our sales process.

We’re looking for a Chief Technology Officer (CTO) who sees technology as a growth and revenue engine — not just an engineering function. You’ll work closely with Sales, and Marketing, to use AI, automation, data, and product to generate more qualified leads, improve conversion, accelerate the sales cycle, and close more transactions.

You’ll inherit real, revenue-generating technology, a talented team, and the opportunity to create the technology strategy that will help Sell2Rent scale faster and sell more.

If you’re excited about using technology to drive measurable business results, this is your opportunity to make a major impact.

Technology strategy. You set the direction: architecture, build-vs-buy, which platforms we standardize on, where AI is a genuine advantage and where it's a distraction. You'll be the person in the room who knows what's actually possible and what it costs.

The engineering organization. You lead a distributed team of roughly ten across engineering and data, all of them in Latin America. You'll grow it, structure it, and set the bar. 

Scaling the platform. Our twelve-month mandate is to ship the roadmap and scale what we've built — completing the migration off legacy systems, hardening the platform, and getting to a place where the business can grow transaction volume without engineering becoming the bottleneck.

The AI layer. Agents handle a meaningful share of our qualification, outreach, and internal operations today. Deciding how far that goes — and building it so it's a durable advantage rather than a demo — is one of the most interesting problems here.

Resilience and continuity. Security, access governance, vendor management, monitoring, documentation, and the discipline that ensures no single person is ever again the only one who knows how something works. We've learned this lesson the expensive way and we're not repeating it.

Executive partnership. You sit on the Executive Committee. You'll work directly with the CEO and the sales, marketing, and operations leaders — translating what the business needs into what gets built, and telling us honestly when what we're asking for is a bad idea.

• 15+ years in technology, with progressive leadership responsibility and time as a CTO, VP of Engineering, or Head of Technology.
  

• You've scaled a team and a system before. Not just managed one — took something from working-but-fragile to reliable-at-volume, and grew the org that did it.
  

• You are technical enough to be trusted, but your job is not to write the code. You should be able to read our architecture, challenge a design decision, and evaluate a vendor on the merits. We have engineers to build. We need someone who can direct them and know when the answer is wrong.
  

• Real depth in AI-driven architecture, cloud infrastructure (we run on GCP), APIs, integrations, and data. Depth, not enthusiasm — you can tell us what LLM-based agents actually break on in production.
  

• You find blind spots. Much of the value in your first six months is telling us what we don't know we're missing — in our architecture, our tooling, our security posture, and our process.
  

• You lead people well. Our team is remote, distributed, and international. Keeping engineers motivated, growing, and clear on what matters is a large part of this job.
  

• Startup-fluent. You're comfortable with ambiguity, limited resources, and making decisions before all the information arrives.
  

• Business-minded. You can connect a technical investment to revenue and defend it to a CEO who will ask.
  

Helpful, not required: real estate, proptech, or fintech experience; running a US-based company with a LatAm engineering team; Spanish.

Our CEO owns product direction and will continue to for the foreseeable future, working closely with the commercial leadership team. You own technology, architecture, and execution. You'll have real influence on what we build and strong input on sequencing — but the product roadmap is not yours to set, and we're not planning to hand it over.

We're stating this plainly because the previous version of this role blended both, and the wrong expectation here makes an otherwise great partnership fail. If owning a product is what you're looking for in your next role, this isn't it.

What success looks like

By 90 days — you know where every system, credential, vendor, and dependency lives, and so does someone besides you. You've told us the three things about our architecture that worry you most. The team knows who they report to, what they're building, and why it matters.

By 6 months — the platform migration is on a credible path, engineering has a real operating cadence, and technology decisions are being made deliberately rather than reactively. You've made at least one hire that raises the bar.

By 12 months — we've shipped the roadmap, the platform handles significantly more volume without more people, and our AI capability is a genuine competitive advantage rather than a set of internal tools. Nothing critical depends on any single individual, including you.

• Location: Remote, with meaningful overlap with US Eastern and Latin America.