Director Of Operations

Company Overview

Host Pros LLC is Northeast Ohio’s leading short-term rental management company, specializing in high-end, large-format properties. We partner with property owners to deliver exceptional guest experiences while protecting and enhancing asset value.

Our team operates on four core principles:

• Don’t Compete, Dominate

• Always Be Curious

• It’s Never Just Business

• Unreasonable Hospitality

If you take pride in your craft, solve problems proactively, and care about delivering excellence, you’ll fit right in.

Position Summary

The Director of Operations is the senior leader responsible for the day-to-day performance of our 80+ property portfolio and the teams that support it.

This is a hands-on leadership role for someone who thrives in high-accountability environments, can lead people with clarity and consistency, and is comfortable owning outcomes across multiple moving parts.

You will oversee Cleaning, Maintenance, Guest Experience, and Field Operations, ensuring every property meets Host Pros’ standards for quality, consistency, and guest satisfaction. You will also serve as the point of contact for operational escalations and key client communication.

This role requires strong decision-making, emotional intelligence, and the ability to anticipate problems before they happen.

What You'll Do

Lead the Operations Team & Culture

• Directly manage:

  • Cleaning Manager

  • Maintenance Technician

  • Runners/Trash

  • Guest Experience Team (Philippines-based)

• Set clear expectations, goals, and standards; hold each person accountable.

• Provide regular feedback and coaching; address performance issues quickly and professionally.

• Model Host Pros' core values daily, especially Unreasonable Hospitality and It's Never Just Business.

• Build a culture of ownership, calm under pressure, transparency, and proactive problem-solving.

Own Client Communication & Escalations

• Serve as the operational point of contact for key property owners.

• Proactively communicate about major incidents, maintenance projects, and performance concerns before clients reach out.

• Handle escalated client and guest issues with diplomacy, clarity, empathy, and decisiveness.

• Deliver hard news professionally, with solutions and next steps.

• Build long‑term trust through reliability, prompt communication, and follow-through.

Drive Operational Excellence Across All Properties

• Maintain an in‑depth understanding of all listings and ensure each meets Host Pros standards.

• Ensure flawless turnovers, consistent quality, and top‑tier guest experiences.

• Ensure the team understands how to operate and troubleshoot amenities (hot tubs, fireplaces, gaming systems, TVs, WiFi, etc.).

• Oversee and ensure effective use of property technology (smart locks, cameras, apps, etc.).

• Ensure issues involving critical systems (e.g. HVAC, plumbing) are triaged and resolved quickly.

• Maintain situational awareness around weather, seasonal demands, and high‑impact events.

Vendor, Cleaner, and Contractor Management

• Work with cleaning manager to set and enforce cleaning standards across all properties, including delivering difficult feedback when necessary.

• Manage maintenance vendors and recruit qualified tradespeople.

• Oversee larger owner projects and ensure they finish on time and meet quality standards.

Guest Experience & Field Support

• Oversee Guest Experience to ensure fast, friendly, accurate guest communication.

• Step in on complex or escalated guest issues requiring judgment, tone, and leadership.

• Develop and implement training programs for Cleaning, Onboarding/QC, Guest Experience, and Runners.

• Occasionally support critical guest experience tasks that require leadership presence.

Systems, Partners & Continuous Improvement

• Manage vendor relationships with platforms such as Guesty, TouchStay, and Breezeway.

• Negotiate better pricing and terms with vendors.

• Identify operational bottlenecks and implement systems and SOPs to address them.

• Lead the weekly L10 Meeting and the weekly Operations Team meeting.

Results (What Success Looks Like)

• Maintain an overall guest review rating of 9.70+ across all listings.

• Meet or exceed the company's annual profitability target.

• Key clients report high satisfaction with communication, responsiveness, and problem resolution.

• Direct reports consistently hit their goals and clearly understand expectations.

• Escalated issues are acknowledged immediately and resolved within defined timeframes.

• Operations run smoothly with minimal surprises, preventable emergencies, or last-minute chaos.

• The team is aligned, engaged, and living Host Pros' core values.

Required Qualifications

Experience & Skills

• 2+ years minimum experience in short term rental operations, boutique hotel hospitality, property management, or facilities management

• General business skills (vendor management, budgeting, prioritization) preferred.

• Basic knowledge of home maintenance and troubleshooting preferred.

• Very comfortable with technology; able to learn new systems quickly.

Leadership & Communication

• Proven experience managing people in a fast‑paced, service‑focused environment.

• Exceptional communication skills - clear, direct, calm, and consistent.

• Demonstrated ability to have hard conversations with professionalism and empathy.

• Strong emotional intelligence and conflict‑resolution skills.

• Comfortable owning problems and driving solutions without hand‑holding.

Mindset & Work Style

• Growth mindset; always looking for ways to improve processes and systems.

• Highly organized with strong follow‑through; does what they say they'll do.

• Able to handle stress, shifting priorities, and unexpected operational challenges.

• Acts with urgency, responsibility, and attention to detail.

Logistics

• Must be located in Northeast Ohio.

• Must have a valid driver's license and reliable transportation.

• Must be willing to work Wednesday–Sunday and be on call for emergencies.

Compensation & Benefits

Annual Salary $90,000 - $100,000

Bonus

• Quarterly, based on review score metrics. Up to 10% bonus per year (2.5% per quarter) if goals hit

Benefits

• Paid time off such as PTO, sick days, and vacation days

• Health insurance, Dental, and Vision insurance

• Commuting/travel assistance

• Telecommuting options

Schedule

This is a leadership role with significant responsibility and autonomy. While core working days are Wednesday through Sunday, the position requires flexibility and availability for urgent operational matters as they arise. You'll have the freedom to manage your time effectively while ensuring seamless operations across all properties.