[Hiring] Customer Service Manager @Better Talent

Role Description

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 using AI tools like Claude/Cowork and our Trellis agent platform (including our guest-facing AI agent, Holly).

You are the human who orchestrates the machines:

• Designing, training, and refining the automations that handle the bulk of guest communication.
• 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 to handle 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 guest communication across all channels and throughout the full guest lifecycle, including pre-booking inquiries, in-stay support, checkout, and post-stay follow-up.
• Lead the customer service department to maximize automation of guest communications and workflows using Halo's AI stack (Trellis agents, including Holly, Claude/Cowork, and messaging platforms).
• Design, test, monitor, and continuously improve AI-driven message flows, agent prompts, macros, and automations while expanding automation coverage and protecting the guest experience.
• Own the human-in-the-loop process by reviewing AI outputs, catching what automation misses, and stepping in when a human touch is needed.
• Handle guest escalations and complaints professionally, resolving issues quickly while protecting review scores.
• Staff, train, schedule, and develop the customer service team (VAs and contractors) while maintaining high quality standards.
• Ensure information flows smoothly between guests, customer service, housekeeping, property care, and operations so nothing falls through the cracks.
• Maintain and improve knowledge bases, SOPs, property information, and canned responses that support both AI and human agents.
• Drive and maintain a 4.9+ star review rating across all Halo listings, treating guest reviews as a key performance metric.
• Monitor and report on KPIs including review ratings, automation rate, response time, resolution time, and guest satisfaction.
• Identify recurring guest issues and turn them into automation improvements and operational fixes.
• Coordinate team coverage to ensure fast guest response times.

Qualifications

• 2+ years of guest services or customer support experience within short-term rentals or hospitality, including team lead or management experience.
• Genuine enthusiasm for AI tools, with hands-on experience using (or a strong desire to master) Claude/Cowork, Trellis, or similar AI and automation platforms.
• Experience building or managing automated workflows, chatbots, message automations, or AI agents is a major plus.
• Excellent spoken and written English with warm, clear, and professional communication across phone, text, and email.
• Strong problem-solving and de-escalation skills with the ability to remain calm under pressure.
• Experience with property management systems, guest messaging software (Hostaway preferred), task management tools, and Google or Microsoft Office.
• Highly organized, self-directed, and dependable, with the ability to thrive in a remote work environment.
• Strong, reliable internet connection and a quiet, professional home office.
• Ability to work hours aligned with U.S. Eastern Time.
• Guest OTA escalation experience is a plus.
• Experience with Conduit is a plus.

Compensation & Benefits

• Base Salary: $1,500–$1,800 USD per month, based on experience and AI/automation aptitude.
• Performance bonus tied to automation rate and guest review/CSAT scores.
• 13th-month pay.
• Paid Time Off (PTO).

Schedule

• Monday–Friday, 8:00 AM–5:00 PM U.S. Eastern Time.

Job Type

• Full-time

Location

• Remote (Colombia)
• Must be available to work U.S. Eastern Time business hours.