Head of Operations, Tailwind

This is not your typical job description. My name is Ari, founder of Extenteam. I entered the short term rental industry by mistake while studying Industrial Engineering at USC 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.

Tailwind is redefining guest communication and the day to day operations of vacation rental operators. 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 are building a new team that has an ownership mindset, values execution, and takes pride in doing excellent work with urgency. If you are someone who pushes for automation, understands patterns in how people work, avoids solving problems by adding headcount, and is committed to improving processes through data, we want to speak with you.

This role is the Head of Tailwind Operations. You will manage a team across time zones, partner directly with upper management, and act as the systems architect responsible for translating operational chaos into scalable, tech enabled frameworks.

You will design the structure, build the processes, and implement the solutions with full ownership. If you enjoy diagnosing complex problems, building structured systems, and executing quickly, this role is ideal. This is consulting meets operations with the authority to implement what you design.

Record a short one minute video explaining why you want to be part of Extenteam.Below are the standard parts of the job description.

• Own all Tailwind operations
• Create scalable frameworks for service delivery, accuracy, and efficiency
• Partner with Product and Engineering on automation and roadmap decisions
• Develop strategies to reduce partner churn and expand service offerings
• Design operational models for future SaaS features

• Prioritize automation across all areas of operations to reduce manual work and increase efficiency
• Lead the design and implementation of automation initiatives with Product and Engineering
• Rebuild metrics for calls, SLAs, queue performance, and accuracy to support automation and real time monitoring
• Oversee the performance, structure, and outcomes of a 24/7 multi time zone operation
• Manage the team responsible for designing workflows, decision trees, and escalation paths that support automation
• Work with internal teams to standardize and improve all partner knowledge bases to enable automated use of information
• Oversee partner onboarding and ensure processes are automation ready from day one

• Work with Finance on cost modeling and unit economics
• Provide operational input to Product and Engineering
• Partner with Sales on pricing, service tiers, and scaling plans
• Build systems that give Partner Success real time insights, predictive alerts, and automated recommendations to improve partner outcomes
• Manage technology vendors to ensure tools, systems, and integrations improve internal efficiency and reduce manual work

A centralized framework that pulls Airbnb and Vrbo reviews through integrations through an API, organizes them in Airtable, surfaces sentiment and response needs, and routes each review to the correct workflow. This includes automated detection of new reviews, review classification, templated response suggestions, and partner-level visibility.

1. Guest Upsell System V1

A structured upsell framework that prompts Tailwind agents to proactively reach out to guests with revenue-generating offers such as early check-in, late checkout, mid-stay cleans, stay extensions, parking passes, pet packages, or premium amenities. This system includes automated triggers, standardized messaging, partner rules, and conversion tracking to drive measurable revenue impact.

1. Pre-Stay Task Automation Engine

A system that reads reservation and check in data from PMS platforms and automatically triggers operational tasks 24 or 48 hours before check in. These tasks include functions such as turning on pool heat, verifying guest identities, registering guests with community or HOA portals, collecting required documentation, and pre-authorizing deposits or fees. The engine can either complete these tasks automatically or route them to the correct Tailwind agent when human action is required, depending on partner specific rules.

• 5+ years at a top consulting firm or in a high-growth company or startup in a systems-focused strategic operations role
• Experience managing or improving service operations
• Proven ability to build systems and processes from the ground up
• Hands-on experience designing automation-ready workflows, knowledge bases, or decision trees in partnership with Product and Engineering.
• Experience working cross-functionally with Product, Engineering, Finance, and Sales to drive operational efficiency, automation, and cost improvements.
• Experience with vendor management, internal tools, or integrations that improve operational efficiency.
• Comfort working with data, dashboards, and analytics tools to create visibility and guide decisions.

Preferred Experience

• Experience leading or scaling a 24/7, multi-time-zone service operation.
• Strong familiarity with operational metrics such as SLAs, accuracy, utilization, queue performance, and service delivery KPIs.
• Background with operational automation, AI-enabled tooling, workflow orchestration, or system integrations.

Systems Thinker You understand how all parts of an operation connect and design structures that work at scale efficiently and predictably..

Execution Focused You move ideas into production quickly and consistently deliver measureable results.

Technically Fluent You understand how systems integrate and can work directly with engineering and product teams.

High Velocity You thrive in fast-paced environments, iterate quickly, and maintain momentum without sacrificing quality.

Strong Communicator You convey information clearly and influence cross-functional teams to bring clarity to complex problems.

Ambiguity Crusher You bring clarity to messy, unclear, or incomplete situations and create order that others can follow.