Head Innkeeper

Location: Homestead, Madison, CT — 11-room B&B

Employment: Full-time; on-site presence required; schedule primarily Thursday–Monday

Homestead is a family‑run, third‑generation 11‑room bed & breakfast in Madison, CT, known for excellent reviews, warm service, and a kind, experienced staff. We prioritize authentic hospitality, community connections, and well‑run operations.

We’re hiring a hands‑on Head Innkeeper to partner with the owners and lead day‑to‑day operations. You will oversee the innkeeping team, ensure outstanding guest experiences, manage housekeeping and contractors, and drive reservation, review, marketing, and event coordination.

• Lead and supervise 3–6 innkeepers (seasonal variation); recruit, onboard, coach, and conduct performance reviews; make hiring/firing decisions in coordination with owners.
• Oversee guest experience: welcome guests, handle escalations, ensure smooth check‑ins/check‑outs, and maintain high service standards.
• Manage online reservations, room pricing, OTAs, and guest review responses; optimize occupancy and reputation.
• Coordinate housekeeping and laundry contractors; enforce cleanliness and room standards.
• Schedule and supervise staff coverage (primary shifts for head innkeeper Thurs–Mon; peak‑season expectations apply).
• Coordinate maintenance and contractors for property upkeep; perform/arrange basic repairs as needed.
• Manage inventory and purchasing for rooms, breakfast, and supplies; approve purchases within delegated authority.
• Plan and coordinate on‑site events and local partnerships to drive bookings and guest value.
• Maintain basic financial records (cash handling, POS oversight) and report operational metrics to owners including cost savings.
• Ensure compliance with health, safety, and licensing requirements.

• Prior hospitality experience preferred; experience in a B&B, small hotel, or guesthouse a plus.
• Proven supervisory experience and strong people‑management skills.
• Comfortable with reservation systems/OTAs, POS, and basic operational bookkeeping.
• Comfortable with digital tools including reservation systems, Microsoft Office and Google.
• Excellent communication, problem‑solving, and guest‑service orientation.
• Hands‑on, approachable, team‑player attitude; able to lead by example.
• Ability to lift at least 30 lbs and perform physical tasks (moving supplies, climbing stairs, etc.).

• Oversee staffing, performance reviews, hiring/firing (in coordination with owners).
• Manage inventory purchases and recommend room pricing adjustments for owner approval.
• Coordinate and approve contractor work within agreed budgets.

Competitive salary $60K–$70K, opportunity to shape a well‑regarded, family‑run property, supportive team environment, and meaningful leadership role.