Online Chat Representative (work from home)

Company: Pentagoet Inn

Location: Remote

Type: Part-Time or Full-Time

About the Role

As an Online Chat Representative at Pentagoet Inn, you’ll be the friendly voice behind the screen, answering real-time guest inquiries, assisting with bookings, and providing helpful information about our inn and the Castine area. You’ll help create meaningful first impressions and ensure potential guests feel welcomed, informed, and excited about their stay.

What You’ll Be Doing

Respond promptly and warmly to live chat messages on our website and booking channels

Provide accurate information about room availability, amenities, local attractions, and policies

Assist with the online booking process and handle basic troubleshooting

Route more complex requests to the appropriate team members when needed

Maintain detailed records of guest inquiries and responses

Offer personalized service that reflects the inn’s thoughtful and traditional hospitality

Collaborate with the reservations and on-site team to ensure seamless communication

Who You Are

You’re an excellent written communicator who enjoys being helpful and resourceful. You understand that even a brief chat can shape a guest’s impression of our inn. You’re courteous, clear, and calm—able to convey warmth and professionalism with every message.

You might be a great fit if:

You have a genuine passion for customer service and hospitality

You’re comfortable multitasking and managing multiple chat windows

You’re detail-oriented and enjoy providing tailored, helpful responses

You’re tech-savvy and adaptable to new systems or tools

Minimum Qualifications:

1+ year of experience in customer service, online support

Strong written English skills with an ability to convey tone through text

Familiar with chat support tools such as Intercom, Zendesk, or similar platforms

Able to work flexible hours, including evenings or weekends if required

Quiet home office with stable internet connection

Why Join Us

At Pentagoet Inn, we believe hospitality begins long before a guest walks through our doors. As part of our remote team, you’ll play a key role in preserving our tradition of personal, heartfelt service while helping us grow into the digital age. We’re a small, collaborative team that values both professionalism and warmth.

Pentagoet Inn is an equal opportunity employer. We welcome applicants from all backgrounds and are committed to building a supportive and inclusive environment.