Head of Operations, Shared Services (US)

Extenteam Careers•Miami, FL

6d•$137,000•Remote

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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
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

Benefits

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
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%)
Remote-first with Miami roots: Work remotely with a talented team, with occasional in-person time at our Downtown Miami office.

Stand Out From the Crowd

Upload your resume and get instant feedback on how well it matches this job.

Upload and Match Resume