Head of Operations, Shared Services (US)

Head of Shared Services Operations

About the Role

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 focused on the wrong things and instead of executing, we spent too much time strategizing.

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 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.

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 not primarily about managing a team. A dedicated Customer Support Lead will oversee day-to-day agent performance, SLA monitoring, and team operations. Your mandate is to operate one level above by building the systems, automation frameworks, and revenue-generating structures that make Tailwind's shared services business scalable, defensible, and profitable.

What You'll Own

Strategic Leadership

• Own the strategic direction of Tailwind shared services operations

• Create scalable frameworks for service delivery, accuracy, and efficiency

• Partner with Product and Engineering on automation priorities and roadmap decisions

• Design operational models for future SaaS features and service tiers

• Develop strategies to reduce partner churn and expand service offerings

• Identify and build new revenue streams including upsell programs and scalable partner-facing products

• Work with Sales and Finance to build pricing frameworks, capacity models, and business cases for new offerings

Operational Excellence

• Prioritize automation across 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

• Oversee the outcomes of a 24/7 multi-time-zone operation with the Customer Support Lead

• Manage the team designing workflows, decision trees, and escalation paths

• Standardize and improve partner knowledge bases to support automation

• Ensure partner onboarding processes are automation-ready from day one

Cross-Functional Work

• Work with Finance on cost modeling, unit economics, and revenue contribution

• 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 and predictive alerts

• Manage technology vendors and ensure systems improve internal efficiency

Examples of Systems This Role Will Build

Review Management System

A centralized framework that pulls Airbnb and Vrbo reviews through API integrations, organizes them in Airtable, analyzes sentiment, and routes reviews to the correct workflow with templated response suggestions and partner visibility.

Guest Upsell System

A structured upsell framework that prompts Tailwind agents to offer early check-in, late checkout, mid-stay cleans, stay extensions, parking passes, pet packages, and premium amenities. The system includes automated triggers, standardized messaging, partner rules, and conversion tracking.

Pre-Stay Task Automation Engine

A system that reads reservation and check-in data from PMS platforms and triggers operational tasks 24 or 48 hours before check-in. Examples include pool heat activation, guest verification, HOA registration, document collection, and deposit pre-authorization.

Shared Services Revenue Reporting

A framework that tracks revenue generated through shared services operations including upsell conversion rates, service adoption, partner ROI, and automation-driven revenue.

Who You Are

Required

• 5+ years at a top consulting firm or high-growth company in a strategic operations role

• Experience improving or managing service operations

• Proven ability to build systems and processes from the ground up

• Experience designing automation-ready workflows or decision trees

• Experience working cross-functionally with Product, Engineering, Finance, and Sales

• Experience with vendor management and operational tooling

• Comfortable working with data, dashboards, and analytics tools

• Ability to build new revenue streams or commercial programs inside operations

This role is remote. Occasional travel to our Miami office will be expected.

Preferred Experience

• Experience leading or scaling a 24/7 multi-time-zone operation

• Familiarity with SLAs, utilization, queue performance, and service KPIs

• Experience with automation, AI tooling, or workflow orchestration

• Experience designing upsell systems, pricing models, or partner success frameworks

Key Attributes

Systems Thinker

You understand how complex operations connect and design structures that scale.

Execution Focused

You move ideas into production quickly and deliver measurable results.

Revenue Oriented

You connect operational improvements directly to revenue growth.

Technically Fluent

You understand how systems integrate and collaborate effectively with product and engineering teams.

High Velocity

You thrive in fast-paced environments and maintain momentum.

Strong Communicator

You bring clarity to complex problems and influence cross-functional teams.

Ambiguity Crusher

You bring structure to messy or unclear situations

Why Join Extenteam

• Build from the ground up and shape shared services operations

• Work directly with senior leadership including the founder

• Own revenue-generating programs within operations

• High autonomy and ownership

• Opportunity to build and lead a team as we scale

• Competitive compensation: $137,000 base + 20% bonus + equity (0.25% to 0.75%)

• Remote-first company with Miami roots

Interview Process

Intro call with Founder (30 min)

Hiring manager interview (60 min)

Case study or take-home assignment

Team interviews

Reference checks and offer

We move quickly for the right candidate.