Job Title: Director Operational Excellence
Location: Remote (U.S.) with regular travel to Chicago, IL. This role requires periodic onsite collaboration with executive leadership, cross-functional teams, and key stakeholders. Travel is expected approximately 20–30%, depending on business needs
Salary: $150,000 - $170,000 Base Salary + Bonus (OTE $160,000 - $220,000)
Skills: Operational Strategy & Process Optimization, Multi-Site Operations Leadership, Systems Design & Workflow Automation, Cross-Functional Project Management, Data Analytics & Performance Improvement
About Company / Opportunity:
A rapidly growing, technology-driven luxury hospitality company transforming the short-term rental industry through automation, operational excellence, and data-driven decision making. Focused on delivering five-star guest experiences, the organization combines premium accommodations with innovative technology to create seamless stays for travelers and scalable operations for property owners. With an entrepreneurial, high-performance culture, the company values speed, accountability, continuous improvement, and exceptional execution as it expands into new markets across the United States.
The City Operations Architect is a strategic operations leadership role responsible for designing, building, and optimizing the operational framework for a growing metropolitan market. This position focuses on creating scalable systems, standardized processes, and technology-enabled solutions that improve efficiency, service quality, and profitability across all aspects of property operations. Working cross-functionally with operations, customer success, technology, revenue, and supply chain teams, the role leads process improvement initiatives, operational audits, market launches, and continuous optimization efforts. Based remotely within the United States with regular travel to Chicago, this individual will play a critical role in developing operational best practices that can be replicated as the organization expands into additional cities.
Responsibilities:
Operational Strategy & Market Design
- Design scalable operational frameworks for the Chicago market that can be replicated across future cities.
- Create standardized operating procedures for property onboarding, inspections, housekeeping, maintenance, inventory, and guest support.
- Evaluate existing workflows and redesign processes to improve efficiency, quality, and profitability.
- Lead operational readiness for new property launches and market expansion initiatives.
Process Improvement & Automation
- Identify operational bottlenecks and implement technology-driven solutions.
- Partner with Product and Engineering teams to improve internal tools and automation.
- Develop workflows that reduce manual work while improving speed and consistency.
- Leverage AI and operational analytics to improve forecasting, scheduling, and decision-making.
Field Operations Leadership
- Conduct regular visits throughout Chicago to evaluate property standards and operational performance.
- Perform operational audits and identify improvement opportunities.
- Coach local vendors and operations partners on Cloud9 standards.
- Lead cross-functional problem solving for complex operational challenges.
Performance & Analytics
- Develop KPIs and operational scorecards for city performance.
- Monitor guest satisfaction, turnaround times, maintenance response, property readiness, and operational costs.
- Present recommendations and business cases to executive leadership.
- Drive continuous improvement initiatives based on operational data.
Cross-Functional Collaboration
- Partner with Customer Success to improve the guest journey.
- Work with Revenue Management to maximize occupancy while maintaining operational readiness.
- Coordinate with Supply Chain to optimize inventory and vendor performance.
- Support Finance with budgeting and operational forecasting.
Must-Have Skills:
- Operational Strategy & Process Design
- Proven ability to build scalable operating models, develop SOPs, optimize workflows, and standardize operations across multiple locations.
- Multi-Site Hospitality or Property Operations Leadership
- Experience leading operations across hotels, luxury vacation rentals, property management, or other multi-unit service environments with accountability for performance, quality, and execution.
- Technology, Automation & Data-Driven Decision Making
- Demonstrated success implementing operational technology, leveraging automation, and using KPIs, dashboards, and analytics to improve efficiency, guest satisfaction, and profitability.
Nice to Have Skills:
- Luxury Hospitality or Short-Term Rental Experience
- Experience with luxury hotels, boutique hospitality, vacation rentals, or property management where service excellence and guest experience are critical.
- Lean Six Sigma / Continuous Improvement Methodologies
- Formal training or hands-on experience applying Lean, Six Sigma, Kaizen, or other continuous improvement frameworks to streamline operations and drive measurable results.
- AI, Automation & Hospitality Technology
- Experience implementing AI-enabled tools, workflow automation, property management systems (PMS), CRM platforms, or other operational technologies that improve efficiency and scalability.