Description
automation
workflow design
metrics
real-time insights
cost modeling
vendor management
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.
You will design the structure, build the processes, and implement the solutions with full ownership. If you enjoy diagnosing complex problems, building structured systems, and executing quickly, this role is ideal. This is consulting meets operations with the authority to implement what you design.
You will manage a team across time zones, partner directly with upper management, and act as the systems architect responsible for translating operational chaos into scalable, tech enabled frameworks.
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.
Record a short one minute video explaining why you want to be part of Extenteam.
A centralized framework that pulls Airbnb and Vrbo reviews through integrations through an API, 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.
- Create scalable frameworks for service delivery, accuracy, and efficiency
- Partner with Product and Engineering on automation and roadmap decisions
- Design operational models for future SaaS features
- Build from the ground up: Shape shared services operations systems and processes—this is your chance to leave a mark
- Provide operational input to Product and Engineering
- Own all Tailwind operations
- Partner with Sales on pricing, service tiers, and scaling plans
- 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
- Oversee the performance, structure, and outcomes of a 24/7 multi time zone operation
- Work with Finance on cost modeling and unit economics
- Rebuild metrics for calls, SLAs, queue performance, and accuracy to support automation and real time monitoring
- Executive visibility: Report directly to the senior leadership and collaborate with the whole leadership team including Founder & CEO
- Work with internal teams to standardize and improve all partner knowledge bases to enable automated use of information
- Manage technology vendors to ensure tools, systems, and integrations improve internal efficiency and reduce manual work
- Develop strategies to reduce partner churn and expand service offerings
- Oversee partner onboarding and ensure processes are automation ready from day one
- Manage the team responsible for designing workflows, decision trees, and escalation paths that support automation
- Build systems that give Partner Success real time insights, predictive alerts, and automated recommendations to improve partner outcomes
Requirements
automation
ai tooling
kpis
service ops
5+ years
systems thinker
You move ideas into production quickly and consistently deliver measurable results.
High Velocity
You convey information clearly and influence cross-functional teams to bring clarity to complex problems.
Execution Focused
You thrive in fast-paced environments, iterate quickly, and maintain momentum without sacrificing quality.
Ambiguity Crusher
Systems Thinker
Technically Fluent
You bring clarity to messy, unclear, or incomplete situations and create order that others can follow.
3. Pre-Stay Task Automation Engine
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.
You understand how systems integrate and can work directly with engineering and product teams.
1. Review Management 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.
2. Guest Upsell System V1
Strong Communicator
- Case study or take-home assignment
- Hands-on experience designing automation-ready workflows, knowledge bases, or decision trees in partnership with Product and Engineering.
- Comfort working with data, dashboards, and analytics tools to create visibility and guide decisions.
- Background with operational automation, AI-enabled tooling, workflow orchestration, or system integrations.
- Strong familiarity with operational metrics such as SLAs, accuracy, utilization, queue performance, and service delivery KPIs.
- Experience leading or scaling a 24/7, multi-time-zone service operation.
- Reference checks and offer We move quickly for the right candidate. You can expect to complete the process within 2-3 weeks.
- Must be within commutable distance of Miami, Florida or be willing to relocate
- Proven ability to build systems and processes from the ground up
- Experience with vendor management, internal tools, or integrations that improve operational efficiency.
- Experience working cross-functionally with Product, Engineering, Finance, and Sales to drive operational efficiency, automation, and cost improvements.
- 5+ years at a top consulting firm or in a high-growth company or startup in a systems-focused strategic operations role
- Hiring manager Interview (60 min)
- Experience managing or improving service operations
Benefits
- Competitive compensation: $100k - $140k base + 15% bonus + equity (0.25%-0.75%)
- Growth trajectory: As we scale, you'll build and lead a team
- Team interviews
- Miami-based team: Work alongside a talented, in-office team 4 days/week in Downtown Miami
Training + Development
Information not given or found
