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.
About the Role
Extenteam seeks an innovative and organized Head of Operations to lead cross-functional teams across finance, customer success, talent, product and data, drive growth, and enhance operational efficiency.
Reporting directly to the Founder, this role involves building, improving, and maintaining scalable operational processes to ensure a solid foundation for continued growth.
Key Responsibilities:
Oversee day-to-day operations of the business, ensuring targets are met or exceeded.(Re)define and establish KPIs and performance metrics for operations and leadership teams to drive accountability and success.(Re)develop and optimize scalable processes and systems to enhance efficiency and support growth.Provide regular updates to leadership, emphasizing operational performance, key insights, and growth opportunities.Lead high-priority projects, ensuring alignment with corporate goals and timely execution.Prepare detailed reports and analyses to support data-driven decision-making.Oversee the implementation of operational improvements to meet strategic growth objectives.Foster a collaborative, high-performance culture aligned with the company's values and objectives.Manage and enhance remote work technologies to boost team productivity and connectivity.Take initiative, execute with excellence, embrace continuous learning, and consistently strive for improvement.Requirements:
Proven Experience: A minimum of 6–8 years in management consulting, senior operations, or leadership roles, ideally in financial services, private equity, or tech/SaaS environments.
Demonstrated success in scaling organizations, such as growing revenue from $10M to $50M ARR, while implementing effective operational strategies.
Experience driving transformative initiatives, such as transitioning from a services-based to a product-based model, or from a sales-led to a product-led growth strategy.
Expertise in financial modeling, data validation, and analysis, with advanced proficiency in Excel and exposure to tools like QuickBooks Online, HubSpot, ATS platforms, and project management tools such as ClickUp.Analytical Skills: Strong analytical background with experience working with large data sets, extracting insights, and building dashboards using no-code integrations.
Expertise in data-driven decision-making, including the use of financial analysis to evaluate ROI and optimize operational efficiency.Financial Acumen: Deep understanding of financial principles, including forecasting, budgeting, and internal auditing, to support strategic decision-making and operational improvements.Strategic Thinker: Ability to develop and execute long-term strategies that align with organizational goals and adapt to the dynamic nature of the role, which evolves approximately every 6 months.
Strong process-driven mindset with exceptional attention to detail, ensuring scalable and efficient operational practices.Leadership: Proven ability to build, lead and inspire globally distributed teams, bringing out the best in diverse talent across multiple time zones and cultures.
Track record of fostering collaboration and building high-performing teams in fast-paced, remote working environments.
Proactive problem solver who thrives in ambiguity, takes initiative, and effectively addresses complex challenges with minimal guidance.Exceptional Communication: Excellent organizational, verbal, and written communication skills, with the ability to align cross-functional teams and engage stakeholders at all levels effectively.
Hands-on experience implementing innovative tools to enhance team collaboration and ensure seamless execution.Adaptability: Comfortable operating in a high-growth, fast-paced environment with changing priorities.
Flexibility to work across time zones and manage remote team dynamics effectively.Additional Requirements: Willingness to spend 2–4 weeks with the founder in Miami or Europe during the onboarding period.
Flexibility to travel up to 30% of the time within the U.S. and EU.Salary will be determined based on experience and geographic location.Competitive base salary with eligibility for an annual cash bonus.Flexible work schedule and generous vacation policy.Remote work opportunities with occasional travel requirements.Apply for this job* indicates a required field
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