Customer Service Manager

Location: Remote (Philippines or Latin America), working hours aligned to U.S. Eastern Time
Category: Hospitality / AI Operations
Job Type: Full-Time
Reports To: Director of Operations
Team: Lead a team of 3–4 VAs/contractors

Company Overview

Halo Hospitality is a full-service short-term rental management company based in Knoxville, Tennessee, managing 80+ properties across the Knoxville and greater East Tennessee market.

We handle everything for our owners, including listing optimization, dynamic pricing, guest experience, housekeeping, and maintenance, so they can own with confidence and earn without the headache.

We are building one of the most automated, AI-native operations in the short-term rental industry, and we're looking for a leader who is genuinely excited to build the future of guest service with us.

Position Summary

This is not a traditional guest-services job. As Halo's Customer Service Manager, your mandate is to lead our customer service team to maximize automation across guest communications and workflows while elevating the guest experience. You'll run Halo's internal AI agent platform and own our guest-facing AI agent, alongside tools like Claude.

You are the human who orchestrates the machines: designing, training, and refining the automations that handle the bulk of guest communication, while owning the judgment calls, edge cases, and escalations that AI can't. You'll lead a lean, high-leverage team, build the systems that keep guest information flowing smoothly at all times, and personally step in on the escalations that matter most.

The ideal person is part operator, part builder: someone who lights up at the idea of teaching an AI agent to do something well, then measuring the result and pushing the automation rate higher. You think in systems, you obsess over response time, guest satisfaction, and protecting our 4.9+ review ratings, and you'd rather build a workflow once than answer the same question a hundred times.

Responsibilities

• Own every guest conversation: Run guest communication across all channels and the full guest lifecycle (pre-booking inquiries, in-stay support, checkout, post-stay follow-up), and coordinate team coverage so response times stay fast.

• Build and tune the automation: Design, test, monitor, and continuously improve the AI-driven message flows, agent prompts, macros, and automations across Halo's AI stack and messaging platforms.

• Own the human-in-the-loop layer: Review AI outputs, catch misses, and intervene before a small miss becomes a bad stay.

• Handle escalations personally: Take guest escalations and complaints directly and protect our review scores.

• Lead the team: Staff, train, schedule, and develop the CS team (VAs and contractors), and set the QA standards they work to.

• Keep information flowing: Make sure guests, CS, housekeeping, property care, and operations always have what they need from each other.

• Maintain the knowledge that powers it all: Own the knowledge bases, SOPs, property info, and canned responses behind both AI and human agents, and turn recurring guest issues into automation and operational fixes.

• Measure and report: Track and report KPIs: average review rating (4.9+ across all listings, a primary success metric), automation rate, response time, resolution time, and guest satisfaction.

• Handle administrative work: Own recurring weekly and monthly administrative responsibilities, plus specific project-based tasks as assigned.

What Success Looks Like in Your First 90 Days

• Guest escalations handled independently, with care and professionalism.

• 3+ workflows built that better support our guests and our team's day-to-day work.

• Proficiency demonstrated with every tool in our tech stack.

• Automation currently handles about 70% of guest messages. Raise that to 85% within 90 days by teaching and training our AI systems.

• Organized, on-time completion of assigned tasks.

• Average review rating held at our target across all listings.

• Documented SOPs and knowledge base for the top recurring guest questions.

Qualifications

• 3+ years in guest services or customer support (STR/hospitality preferred), including at least 1 year leading a team.

• Genuine enthusiasm and aptitude for AI, with hands-on experience with (or a strong drive to master) Claude, ChatGPT, or comparable AI/automation tools.

• Building or operating automated workflows, chatbots, message automations, or AI agents is a major plus.

• Clearly spoken and written English is a must.

• Strong problem-solving and de-escalation skills.

• Experience with property management and guest-messaging software (we run on Hostaway), task tools, and Google Workspace.

• Highly organized, self-directed, and reliable working remotely, with strong, stable internet and a quiet workspace.

• Comfortable working U.S. Eastern hours.

• Guest OTA escalation experience is a plus. Conduit experience is a plus.

Compensation & Benefits

• Base Salary: $1,400–$1,700 per month USD, based on experience and AI/automation aptitude.

• Bonus: Quarterly bonus tied to individual performance and company profit (eligible after 90 days).

• Benefits: 13th-month pay and paid time off (PTO), eligible after 90 days.

• Schedule: Full-time, Monday–Friday, 8:00 AM–5:00 PM U.S. Eastern Time. Nights and weekends are covered by other members of the customer service team.