Job Description

Position Overview

ADRESA is a Chicago-based short-term rental investment and management company. We are seeking an Operations Manager to oversee and scale day-to-day operations across our growing portfolio of short-term rental properties.

This role is responsible for ensuring smooth execution across cleaning, maintenance, quality control, guest readiness, and building operations. The Operations Manager will work closely with field teams, vendors, and leadership to maintain high service standards, strong operational controls, and consistent performance as the portfolio grows.

The ideal candidate is highly organized, process-driven, and comfortable managing multiple moving parts. Experience in short-term rentals, hospitality, property management, or facilities operations is strongly preferred.

Key Responsibilities

Portfolio Operations

• Own full operational performance across all buildings and STR units
• Build and scale operating systems across cleaning, maintenance, guest support, security, and supply chain
• Develop and enforce SOPs, workflows, and escalation paths
• Implement KPIs for cleaners, maintenance techs, QC managers, and concierges
• Lead weekly operations reviews and report performance to leadership

Building & Facilities Management

• Serve as point person for building-level issues including HVAC, plumbing, electrical, elevators, and access control.
• Manage preventative maintenance schedules and oversee unit upgrades and resets

Logistics & Workforce Coordination

• Own daily operational scheduling: check-ins, check-outs, cleanings, maintenance, inspections, and special projects
• Ensure proper staffing coverage and on-time execution
• Anticipate high-volume periods and proactively allocate labor
• Streamline coordination between cleaning, maintenance, QC, and concierge teams

Guest Experience

• Uphold ADRESA’s premium hospitality standards across all units
• Support concierge and CSR teams with escalated on-site guest issues
• Enforce house rules, noise policies, and security protocols
• Coordinate with overnight monitoring and security partners

Vendor & Team Management

• Recruit, onboard, and manage cleaners, maintenance techs, contractors, and vendors
• Negotiate pricing, manage contracts, and hold vendors accountable to quality and timelines
• Oversee procurement and inventory for linens, amenities, supplies, and furniture
• Maintain cost discipline without sacrificing service standards

Systems & Data

• Manage operational platforms including Hostaway, PriceLabs, Breezeway, Google Suite, and reporting tools
• Ensure accuracy across listings, calendars, automations, and communications
• Build dashboards and reporting to track performance, margins, and workflow efficiency
• Lead adoption of tools and integrations to support scale

Growth & Expansion

• Support onboarding of new buildings, units, and renovation projects
• Create launch playbooks including staffing, SOPs, and supply setups
• Identify inefficiencies and drive margin and process improvements
• Partner directly with ownership on operations strategy and scaling roadmap

Qualifications

• 2+ years of experience running multi-unit operations, ideally in short-term rentals, hospitality, or property management
• Proven ability to manage complex operations with high accuracy and minimal oversight
• Strong leadership, communication, and decision-making skills
• Comfortable operating in a fast-growing, evolving environment
• Tech-savvy with experience using PMS platforms, scheduling tools, and reporting dashboards
• Flexible schedule with the ability to respond quickly to high-priority operational issues

Why Join ADRESA

• Competitive USD compensation with commission incentives.
• Opportunity to be at the forefront of a fast-growing STR investment platform.
• Clear path to growth into a senior or partnerships role as the company expands.

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