Carriage Way Inn & Carriage Way Centennial
Part of The Gather Company Collection | St. Augustine, Florida
Create Memorable Stays. Lead with Heart. Love What You Do.
At The Gather Company, we believe hospitality is about more than providing a place to stay—it's about creating experiences guests remember long after they return home.
We are seeking a warm, energetic, and hospitality-driven Innkeeper to help lead the guest experience at Carriage Way Inn and Carriage Way Centennial, two award-winning historic bed & breakfasts in the heart of beautiful St. Augustine.
Working alongside the General Manager, you'll play a vital role in every aspect of the guest journey—from welcoming travelers and preparing breakfast to maintaining beautiful accommodations and supporting daily operations. Every interaction is an opportunity to create genuine connections and deliver exceptional hospitality.
If you've ever dreamed of running a boutique inn where no two days are the same and every guest has a story, we'd love to meet you.
About You
We welcome people from all backgrounds who share a passion for serving others. Our ideal Innkeeper is someone who combines warmth, organization, attention to detail, and an ownership mindset.
Preferred Qualifications
- Two or more years of hospitality, lodging, or hotel leadership experience
- Experience in housekeeping, quality assurance, or property operations
- Success leading or coordinating both front- and back-of-house teams
- Outstanding guest service skills with the ability to resolve concerns professionally and compassionately
- Food & beverage experience (ServSafe Certification is a plus)
- Strong communication and organizational skills
- Comfortable using technology and hospitality software
- Passion for local history, storytelling, and creating memorable guest experiences
- Self-motivated with the ability to work independently while leading a small team
- Able to lift up to 25 pounds and comfortably navigate multiple floors throughout the Inns
What You'll Do
As an Innkeeper, you'll help ensure every day runs seamlessly while delivering thoughtful hospitality that exceeds expectations.
Deliver Exceptional Guest Experiences
- Welcome guests with warmth and professionalism from arrival through departure
- Anticipate guest needs and personalize each stay
- Build authentic connections that inspire outstanding reviews and repeat visits
Create an Exceptional Breakfast Experience
- Prepare and serve beautifully presented breakfasts each morning
- Assist with menu planning, food preparation, presentation, and service
- Create a welcoming atmosphere that starts each guest's day on a high note
Maintain Beautiful Guest Rooms
- Perform housekeeping duties including guest rooms, bathrooms, public spaces, laundry, and room staging
- Maintain exceptional cleanliness and presentation standards throughout both properties
- Ensure every room is guest-ready with meticulous attention to detail
Support Daily Operations
- Assist with scheduling, daily operations, inventory, and team coordination
- Help keep the Inns organized, efficient, and operating at a high level
- Hold yourself and teammates accountable for delivering excellent service
Be a Flexible Team Player
- Jump in wherever needed—from guest service and breakfast to light maintenance and operational support
- Assist during weekends, holidays, and busy occupancy periods
- Embrace the variety that makes boutique hospitality so rewarding
Communicate with Excellence
- Build strong relationships with guests, teammates, and leadership
- Share information clearly and professionally
- Foster a collaborative, positive work environment
Why You'll Love Working Here
At The Gather Company, we believe great hospitality begins with a great team.
You'll enjoy:
- A welcoming, family-oriented culture
- Opportunities for professional growth and advancement
- Supportive leadership invested in your success
- The opportunity to help preserve and operate two of St. Augustine's most charming historic inns
- A workplace where your ideas, initiative, and contributions truly matter
- And yes...the best breakfast in town to start your day!
Compensation & Benefits
Position: Full-Time
Compensation: $20–$25 per hour, based on experience
Benefits
- IRA retirement plan with company matching contributions
- Paid Time Off
- Employee discounts and complimentary stays throughout The Gather Company Collection
- Flexible scheduling with primarily daytime hours
- Daily staff breakfast
- Opportunities for career growth within our expanding portfolio of boutique inns
Join The Gather Company
If you believe hospitality is an art, love creating memorable experiences, and thrive in a hands-on environment where every day brings something new, we'd love to welcome you to our team.
Come help create unforgettable stays—one guest, one breakfast, and one experience at a time.
Pay: $20.00 - $25.00 per hour
Benefits:
- Employee discount
- Flexible schedule
- Food provided
- Free parking
- Paid time off
- Professional development assistance
Work Location: In person
