<h2><strong>Head of Technology & Product</strong></h2>
<p><strong>Extenteam | US or Europe, remote </strong></p>
<h3><strong>About Extenteam</strong></h3>
<p>Extenteam 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.</p>
<p>We are bootstrapped, profitable with no outside capital.</p>
<p>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.</p>
<h3><strong>Why this role exists</strong></h3>
<p>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.</p>
<p>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.</p>
<p>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.</p>
<h3><strong>Non-negotiables</strong></h3>
<p>Three things. If you do not have all three, this is not the right role.</p>
<ol>
<li><strong> You come from the STR industry.</strong> 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.</li>
<li><strong> Engineering background.</strong> 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.</li>
<li><strong> Scrappy.</strong> Small team, no product org beneath you, no analysts. You will be hands-on daily.</li>
</ol>
<h3><strong>Who you are</strong></h3>
<p>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.</p>
<p>You want ownership rather than process. You are joining a company with a real product, real revenue, and real problems, not a blank page.</p>
<h3><strong>What you will own</strong></h3>
<p><strong>Product direction</strong></p>
<ul>
<li>Roadmap and prioritization</li>
<li>North stars and the metrics that define them, including resolving how we measure automation against actual resolution quality</li>
<li>Discovery. Understanding what property managers and customers need, then defining and prioritizing the right problems</li>
<li>Delivery. Staying meaningfully ahead of engineering so work is scoped before it reaches the team</li>
</ul>
<p><strong>Engineering organization</strong></p>
<ul>
<li>Pod structure across the team</li>
<li>A formal performance framework</li>
<li>Decisions on performance</li>
</ul>
<p><strong>Cross-functional</strong></p>
<ul>
<li>The bridge between engineering and the rest of the business, so pressure reaches the team as business context rather than personal criticism</li>
<li>Partnership with Shared Services and Customer Success on what actually needs building, rather than absorbing requests reactively</li>
</ul>
<h3><strong>What this role is not</strong></h3>
<ul>
<li>Not a process role. We are not looking for someone to install a framework and run ceremonies</li>
<li>Not a pure people manager. You are close to the work and technical enough to be credible with engineers</li>
<li>Not a role where the roadmap is handed to you. You own it</li>
<li>Not a role for someone whose industry knowledge is adjacent. Hotels, long-term rental, or general SaaS is not the same as STR</li>
</ul>
<h3><strong>Required experience</strong></h3>
<ul>
<li>10+ years across product and engineering, with time owning both</li>
<li>Directly managed product managers, engineers, or both</li>
<li>Short-term rental, vacation rental, or property management experience</li>
<li>Track record of restructuring a team and improving how it delivers</li>
<li>Experience shipping AI or automation products where coverage and quality trade off against each other</li>
</ul>
<h3><strong>Strongly preferred</strong></h3>
<ul>
<li>Experience at a competitor or adjacent platform in the STR space</li>
<li>Experience building for internal operational users as well as external customers</li>
</ul>
<h3><strong>Location and working hours</strong></h3>
<ul>
<li>US or Europe, remote.</li>
<li>Quarterly in-person meetings, which may be in the US or Europe.</li>
</ul>
<h3><strong>Compensation</strong></h3>
<ul>
<li>Base compensation is determined by location and experience.</li>
<li>Equity is included.</li>
</ul>
