Head OF Operations

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 (Tailwind) that combines AI automation (Autopilot AI) with human-in-the-loop oversight. We are headquartered in Miami with our Shared Services team based in Manila. We are hiring a Head of Shared Services Operations to run our service operation and personally build the operational tooling that makes it scale. The Role This is a builder-operator role, not a manager-of-managers role. You will run the Shared Services operation across three sub-team, and you will personally ship the tools, dashboards, automations, and AI workflows that make the operation better every week. You are not a strategy advisor. You are not delegating work to an engineering team. You build it yourself. You report to the Head of Operations and work directly with our founder. What You Will Own The Shared Services operation across three sub-teams SLA delivery across text and voice channels Enterprise client relationships at the operational layer Daily ops, scheduling, QA, knowledge base, and client escalations Direct relationship with the Contact Center Manager and Team Leads What You Will Build You ship things. Personally. With your own hands. Examples of what you would build in your first 90 days: An anomaly detector that flags AI replies violating OTA platform rules (Airbnb, VRBO ToS) before they reach the guest A daily QA sampling tool that scores AI and agent responses against a rubric and routes failures back into the knowledge base A scheduling model that matches agent shifts to actual guest volume curves by hour and day A live operational dashboard pulling from our internal platform, Aircall, and HubSpot to give us SLA visibility we do not have today A prompt evaluation framework that tracks AI deflection accuracy and surfaces drift before it becomes a client complaint A capacity planning model that lets us run staffing scenarios with live formulas These are not feature requests sent to engineering. These are internal tools that you build because the operation needs them now. What This Role Is Not Not a strategy or PMO role. We do not have analysts or program managers backing you up Not a customer-facing platform engineering role. You are not shipping product code to clients Not a manager-of-managers role. You will be in the work daily, building, debugging, and shipping Not a "hire 20 people to fix this" role. Headcount is constrained by design Required Experience 5+ years of operations leadership at a tech-enabled service business Direct ownership of a customer-facing service operation with measurable SLA, CSAT, or cost metrics Short-term rental, hospitality, or property management operations AI or automation deployed in a live customer-facing operation, with hands-on diagnostic experience when it broke Experience leading distributed teams Required Technical Skills You must be hands-on with at least one of the following stacks, ideally several: Agentic coding tools used in production: Claude Code, Cursor, Replit Agent, or similar, not just for personal projects Workflow automation platforms: n8n, Zapier, Make, or Pipedream Scripting: Python or SQL at a working level, able to write and debug your own queries and scripts Prompt engineering: Designing, evaluating, and iterating on production AI agent prompts We will ask you to show us what you have built. We will ask you to defend the formulas and explain the architecture. If you have never shipped a working internal tool, this is not the right role. Strongly Preferred Direct experience with Guesty, Hostaway, OwnerRez, , or comparable platforms AI deployment in a guest-facing or customer-facing context Compensation $130,000 to $160,000 base plus equity, based on experience. Location US Remote. Quarterly travel to Miami headquarters required. #J-18808-Ljbffr