Head of Operations

About Us
We’re Extenteam, a dynamic company revolutionizing the short term vacation rental industry. Our proven business model has generated consistent revenue, and we are now expanding from a professional services model to a scalable tech-based subscription-first model.

As a scaling stage startup, we aim to grow our Monthly Recurring Revenue (MRR) to double our revenue by January 2026 by providing an AI assisted SaaS platform that works for all short term rental businesses regardless of their size.

Extenteam is on a mission to streamline and support vacation rental businesses by providing top-notch solutions, including guest communication and property management support.

We generate revenue through two primary streams:

• Dedicated Team Members: Providing trained overseas talent with a recurring premium model, replacing one-time recruitment fees.
• Tailwind - SaaS Platform: A guest communication Software blended with our shared services team, supporting smaller operators typically with less than 50 units - helping Extenteam increase profitability while growing our product market fit and expanding TAM and service levels.

Extenteam is a small but mighty team of 50 consisting of Sales, Partner Success, Marketing, HR & Recruiting, Engineering, Product and Admin (IT, Data etc). We are spread out across the world but we have hubs in Miami, LA, Medellin, and actively expanding into Europe. Our 50 people core team is supported by 400+ DTMs (dedicated team members) that are servicing our customers.

Our Values:

• Commitment to Excellence: Continuously raising the bar and setting new standards in guest communications and service delivery. 
• Exceptional Collaboration: Thriving in a fast-paced, high-performance environment built on clear communication and teamwork. 
• Unified Purpose: Aligning behind a shared mission to drive success with an intense focus. One shared consciousness. 
• Data-Driven Decision-Making: Prioritizing data and results over emotions when making objective, professional decisions. 
• Emphasis on Details: Details matter at every level. Leaders are expected to have a deep understanding of the specifics and adopt a hands-on management style.

Our Leadership Philosophy

Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture.

To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link. Understanding this mindset will provide valuable context for how we operate and what we value in our team members. 

 

Head of Operations / Chief of Staff 

Location: Hybrid — New York

Reporting to: Founder & CEO

We're looking for a true operator — someone who’s scaled companies from $10M to $100M+ from the inside. Hands-on. Sleeves rolled up. Solving for complexity, inefficiency, and growth bottlenecks in real time.

This is not a strategist role.

This is not for consultants or managers who sit on the sidelines.

If you’ve lived through the warzone of scale and built the ops machine from the ground up, this is the role for you.

 

About the Role

As Head of Operations, you’ll lead and evolve our operational backbone — overseeing HR, Accounting, Finance, Customer Success, Product Operations, and internal systems. You'll work cross-functionally to ensure we scale with clarity, efficiency, and precision.

You’ll be a key member of the executive team, driving operational excellence across all departments, designing systems that unlock scale, and helping us transition from a services-led company to a product-first business with SaaS-level performance.

 

About Us

We’re Extenteam, a fast-growing company revolutionizing the short-term vacation rental industry. Our proven business model has generated consistent revenue, and we’re now expanding from a professional services model to a scalable, tech-enabled subscription platform.

We’re a tight-knit team of 50, spanning Sales, Partner Success, Marketing, HR & Recruiting, Engineering, Product, and Admin. We operate globally, with hubs in Miami, LA, Medellín, and expanding quickly into Europe. Our core team is backed by 400+ Dedicated Team Members (DTMs) supporting our clients.

Our goal is to double revenue by January 2026 through Tailwind — our new AI-assisted SaaS platform that supports operators of all sizes with guest communication, operational efficiency, and integrated services.

 

How We Work

Our leadership philosophy is inspired by “founder mode,” as championed by Airbnb’s Brian Chesky. That means:

• Being hands-on and visionary
• Staying close to product and customers
• Solving problems directly and creatively
• Working with urgency and ownership

We value proactive leadership, accountability, and radical collaboration. This role is for someone who thrives in that kind of environment.

 

MUST-HAVE REQUIREMENTS — DO NOT APPLY UNLESS YOU CHECK ALL

🚀 Experience Scaling

• Played a hands-on operational leadership role in a SaaS or professional services company that grew from $10M to $100M+ in revenue (or $10M to $50M ARR).
• Built systems, teams, and processes — not from theory, but by doing.
• Has 6–8+ years in senior operations roles ideally in tech, financial services, or private equity.
• Drove transformational growth — such as transitioning from a services-based to a product-based model, or from sales-led to product-led growth.

 

🔧 Operational Excellence

• Deep understanding of operational failure points and how to proactively solve them.
• Able to map processes visually, find inefficiencies fast, and design/implement scalable workflows.
• Comfortable connecting tools and platforms (even without direct API work), with a strong systems-thinking mindset.
• Knowledge with tools like HubSpot, Notion, Slack, Greenhouse and project management tools like ClickUp.

 

📊 Data-Driven Leadership

• Built KPI dashboards and performance tracking systems across functions.
• Used data to drive team accountability, growth, and improvement.
• Strong analytical skills with experience working with large datasets, performing ROI analysis, and building dashboards via no-code tools.
• Advanced proficiency in Excel, with expertise in financial modeling, budgeting, and forecasting.( We have a financial controller, but we want this role to be data driven)

 

🧠 Strategic + Tactical

• Thinks holistically across all operations (HR, CS, Finance Ops, Product, etc.).
• Balances strategic foresight with tactical execution. Gets in the weeds when needed.
• Process-first mindset with high attention to detail, and adaptability in fast-changing environments — understands the role may evolve every 6 months.

 

🤝 People Management & Culture

• Hired and fired in HR and CS functions.
• Led multi-layered, globally distributed teams with clarity and accountability across time zones and cultures.
• Understands how to motivate, coach, and retain top talent in remote, high-performance environments.

 

💬 Clear Communicator & True Collaborator

• Communicates clearly and directly — with the CEO, clients, partners, and team.
• Builds strong relationships across departments and at the leadership table.
• Can challenge and align with the founder constructively, always putting the company first.
• Strong written and verbal communication skills, with a track record of aligning stakeholders and driving execution.

 

🌍 Adaptability & Commitment

• Comfortable operating in a high-growth, fast-paced environment with changing priorities.
• Flexibility to work across time zones and manage remote team dynamics.
• Willingness to spend 2–4 weeks onboarding in-person with the founder (US or Europe).
• This position is a hybrid role - This role follows a flexible hybrid model. To collaborate closely with the founder and other key stakeholders, you’ll join us on-site every other week (or several days each week, if preferred). We don’t enforce a rigid policy, but regular in-person time is important to the founder and is considered essential for your success in the role.

 

Who You Are

• You act like an owner, not an employee.
• You move quickly, see around corners, and sweat the details.
• You’re humble, direct, and deeply competent.
• You don’t look for credit — you look for outcomes.
• You’ve been in the arena, and you want to do it again — this time, even better.

 

Why Join Us

We're building something ambitious and complex, and we need a strong operator to build a world-class operational engine.

You’ll have a seat at the table, real influence, and the chance to do the best operational work of your career.

If this sounds like your kind of challenge — we want to hear from you.