Agent Operations Lead

Introduction

This is not your typical job description. My name is Ari, founder of Extenteam. I got into the short term rental industry by mistake while I was getting my undergraduate degree in Industrial Engineering at USC in California back in 2009.

After running short term rental management companies for more than a decade, I started Extenteam, a staffing and proptech company that helps short term rental operators. We grew to a team of 430 people and more than 10MM ARR, but we also became complacent. We became stagnant. We focused on the wrong things and instead of executing we spent too much time strategizing.

The people we had were great people, but not the right people for the type of company I want Extenteam to be. Everything changed at our South of France offsite in October 2025.

We decided that while our dedicated team member unit remains relevant in the hospitality and real estate industry, the future of the short term rental industry will be shaped by AI and automation. This is where Tailwind comes in. 

Our mission is to help our existing client base of 300 property management companies become more efficient and automate their operational processes using our Tailwind platform.

We want a new team that has an ownership mindset, values execution, and takes pride in doing excellent work with urgency. If you are a person who pushes for automation, understands patterns in how people work, avoids solving problems by adding more headcount, and is committed to improving processes through data, we want to speak with you.

This role will report to the Head of Tailwind Operations. You will manage a team across different time zones and locations.

Record a short one minute video explaining why you want to be part of Extenteam.

Below are the standard parts of the job description.

Role Overview

Tailwind is Extenteam’s automation and guest communication service built specifically for the short term rental industry. It helps property management companies streamline their operations by centralizing guest messaging, automating repeatable tasks, and improving response times across all communication channels. Tailwind reduces manual work and increases efficiency so operators can scale without adding unnecessary labor.

The Team Operations Lead plays a critical role in ensuring daily performance, operational consistency, and scalable systems. You will manage the frontline team, own scheduling and forecasting, and build a performance driven environment grounded in data, structure, and automation.

Key Responsibilities

Day to Day Team Operations

• Oversee daily agent performance and ensure SLA compliance across all shifts.
• Manage adherence, attendance, and scheduling for the 24/7 team.
• Maintain a weekly break schedule that balances coverage and team well being.
• Handle shift swaps and last minute coverage adjustments.
• Verify agent setup compliance including monitors, internet stability, and required tools.
• Maintain consistency across all shifts, teams, and time zones.
• Identify operational patterns in workflows and use these insights to drive automation rather than solving issues through additional staffing.

Workforce Forecasting and Scheduling

• Build schedules based on forecasted reservation and message volume.
• Analyze volume trends using tools such as PowerBi to improve schedule efficiency.
• Develop predictive staffing models that determine when new hires are actually needed and prevent overstaffing.
• Collaborate with engineering and automations to connect data sources and improve forecasting reliability.
• Adjust schedules proactively for seasonal peaks and partner onboarding activity.

Performance Visibility and Accountability

• Own the Performance Management Framework including verbal, written, final warning, and PIP processes.
• Improve visibility of agent performance metrics through a live leaderboard.
• Work with the automation team to ensure accuracy of dashboards and remove manual processes.
• Create bonus systems tied directly to performance data.
• Deliver weekly operational reports covering SLA, adherence, forecast accuracy, and automation opportunities.

Collaboration and Leadership

• Work closely with the Head of Operations to build scalable operational systems.
• Coordinate with Partner Success to ensure service quality meets expectations.
• Promote a culture that values performance, transparency, and data driven decision making.
• Lead the team by identifying their challenges, understanding how they work, and guiding them toward automation first solutions.

Who You Are Required Experience:

• Five or more years of experience in service operations or hospitality.
• Generalist profile with experience supporting international or fast growing companies.
• Proven track record optimizing back office tasks and operational processes.
• Able to analyze how people work, understand workflow patterns, and identify challenges through data.
• Someone who pushes teams to automate instead of adding people to solve operational bottlenecks.
• Highly tech savvy with hands on experience using workforce management and automation tools.
• Strong ownership mindset, urgency, and follow through.
• Experience managing multicultural and remote teams.

  Familiarity with AI driven routing, tagging, and performance analytics tools.