Head of Operations, Shared Services

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: 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, develop, and own new revenue streams for the shared services business, including new service categories, upsell programs, and partner-facing products that can scale without proportional headcount growth.
• Work with Sales and Finance to build pricing frameworks, capacity models, and business cases for new offerings that directly contribute to company revenue targets.

Operational Excellence

• 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 in close partnership with the Customer Support Lead, who owns day-to-day agent performance management.
• 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

Cross-Functional Work

• Work with Finance on cost modeling, unit economics, and revenue contribution from shared services.
• 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
• This role will work closely with the Head of Operations and Chief of Staff as those functions are built out. Exact boundaries and coordination models will evolve based on organizational design, but this role owns the shared services layer and is expected to operate with a high degree of autonomy and cross-functional influence.

 

Examples of High-Impact Systems This Role Will Build

1. Review Management System V1

A centralized framework that pulls Airbnb and Vrbo reviews through API integrations, 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.

2. 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.

This person will also be responsible for designing and launching net-new upsell and monetization programs beyond the initial V1 framework, identifying opportunities to generate incremental revenue for both Tailwind and its property management partners.

3. 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.

4. Shared Services Revenue Reporting

A framework for tracking and reporting the direct revenue contribution of shared services operations, including upsell conversion rates, new service adoption, partner-level ROI, and incremental revenue generated through automation. This creates internal visibility and positions Tailwind shared services as a profit center, not just a cost center.

 

Who You Are

Required

• 5+ years at a top consulting firm or in a high-growth company 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
• Demonstrated ability to identify and build new revenue streams or commercial programs within an operations context.
• Must be within commutable distance of Miami, Florida or be willing to relocate

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
• Experience designing or scaling commercial programs such as upsell systems, pricing models, or partner success frameworks that tie operational performance directly to revenue.

Key Attributes

• 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 measurable results
• Revenue Oriented - You understand that operational excellence without commercial impact is incomplete. You look for leverage points where automation and process improvements translate into measurable revenue growth for the business.
• 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

 

Why Join Extenteam

• Build from the ground up: Shape shared services operations systems and processes. This is your chance to leave a mark
• Executive visibility: Report directly to senior leadership and collaborate with the whole leadership team including the Founder and CEO
• Revenue ownership: You will not just optimize costs. You will be accountable for growing the commercial output of the shared services function and building programs that directly impact the company's top line.
• Ownership and autonomy: We trust you to own your domain and make bold decisions
• Growth trajectory: As we scale, you will build and lead a team
• Competitive compensation: $137,000 base + 20% performance bonus + equity (0.25%-0.75%)
• Miami-based team: Work alongside a talented, in-office team 4 days/week in Downtown Miami

 

Our 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. You can expect to complete the process within 2-3 weeks.

Record a short one-minute video explaining why you want to be part of Extenteam and how you think about building revenue-generating operational systems.