Head of Technology & Product (US or Europe, remote)

Head of Technology & Product

The company | US or Europe, remote

About the company

The company is an AI-driven operations platform for short-term rental property managers. We handle guest communication and daily workflows for over 80,000 properties through a proprietary platform that combines AI automation with human-in-the-loop oversight. We are headquartered in Miami.

We are bootstrapped, profitable with no outside capital.

We are hiring a Head of Technology & Product to own what we build, why we build it, and how the team is organized to build it.

Why this role exists

We have a working product, real revenue, and a team that ships well when the problem is clearly defined. What we do not have is a single owner sitting across product and engineering.

Today we are running two roadmaps with one team. We are building a standalone SaaS product while also supporting a live Shared Services operation, and those two pull in different directions daily. Deciding what wins, and when, needs someone whose job that is.

The same is true of how the team is organized. As we grow past our current size, pod structure, ownership, and a proper performance framework all need a dedicated owner rather than being handled alongside everything else.

Non-negotiables

Three things. If you do not have all three, this is not the right role.

• You come from the STR industry. Short-term rental, vacation rental, or property management. You know what a reservation alteration is, how OTA compliance actually works, and what a property manager loses sleep over. You have opinions about Guesty versus Hostaway versus Breezeway. This is the single most important requirement and we will not compromise on it.

• Engineering background. You have written production code and led engineers. You can judge a technical trade-off without deferring to someone else, and engineers take you seriously because you have done the work.

• Scrappy. Small team, no product org beneath you, no analysts. You will be hands-on daily.

Who you are

You have owned a product roadmap and the team that delivered against it. You have made calls on what does not get built. You have restructured a team because the old shape was wrong, and you have had a conversation with someone who was not performing.

You want ownership rather than process. You are joining a company with a real product, real revenue, and real problems, not a blank page.

What you will own

Product direction

• Roadmap and prioritization

• North stars and the metrics that define them, including resolving how we measure automation against actual resolution quality

• Discovery. Understanding what property managers and customers need, then defining and prioritizing the right problems

• Delivery. Staying meaningfully ahead of engineering so work is scoped before it reaches the team

Engineering organization

• Pod structure across the team

• A formal performance framework

• Decisions on performance

Cross-functional

• The bridge between engineering and the rest of the business, so pressure reaches the team as business context rather than personal criticism

• Partnership with Shared Services and Customer Success on what actually needs building, rather than absorbing requests reactively

What this role is not

• Not a process role. We are not looking for someone to install a framework and run ceremonies

• Not a pure people manager. You are close to the work and technical enough to be credible with engineers

• Not a role where the roadmap is handed to you. You own it

• Not a role for someone whose industry knowledge is adjacent. Hotels, long-term rental, or general SaaS is not the same as STR

Required experience

• 10+ years across product and engineering, with time owning both

• Directly managed product managers, engineers, or both

• Short-term rental, vacation rental, or property management experience

• Track record of restructuring a team and improving how it delivers

• Experience shipping AI or automation products where coverage and quality trade off against each other

Strongly preferred

• Experience at a competitor or adjacent platform in the STR space

• Experience building for internal operational users as well as external customers

Location and working hours

• US or Europe, remote.

• Quarterly in-person meetings, which may be in the US or Europe.

Compensation

• Base compensation is determined by location and experience.

• Equity is included.