General Manager in Callicoon Center, New York at Howard Financial - Internal

Howard Financial is partnering with Callicoon Hills to lead the search for their next General Manager. This is a direct hire role — you will be employed by and working on-site at Callicoon Hills full time.

About Callicoon Hills

Nestled in the heart of the Catskills, Callicoon Hills is a historic resort and event destination with a lot of soul. We have boutique accommodations, a beautiful restored barn for weddings and events, food & beverage programming that reflects the season and the region, and a team that genuinely cares about the people who walk through our doors.

We are part of the 388 Ventures portfolio, and we are in an exciting chapter — building the systems, the team, and the culture that will take this property to its full potential. There is real momentum here, and we are looking for the right person to lead it.

The Opportunity

We are looking for a General Manager who loves this kind of work — not just the title, but the day-to-day reality of running a living, breathing hospitality property. Someone who finds energy in solving problems, takes pride in a well-run operation, and genuinely lights up when a guest has an exceptional experience.

This role leads everything: rooms, housekeeping, maintenance, food & beverage, events, staffing, and financial performance. It is a big job, and we know that. We are looking for someone who is ready for it — and who wants to do it alongside an ownership team that is engaged, supportive, and deeply committed to making Callicoon Hills something special.

• Set the tone for the entire property — leading daily operations across all departments with high standards, genuine care, and a consistent presence that the team can count on
• Be the kind of leader people are glad to see walk in — on the floor, in the kitchen, at the front desk, wherever the energy needs you
• Build a team that feels genuinely supported and proud of where they work, and watch what that does for the guest experience
• Partner with the sales and F&B team to plan and execute weddings and events that guests talk about long after they leave
• Keep ownership informed and aligned — sharing wins, surfacing challenges early, and always following through on what you commit to
• Own the physical quality of the property from top to bottom — because the way a place looks and feels tells guests everything about how much you care
• Collaborate with ownership to build the systems and processes that make great operations sustainable and scalable
• Show up personally for the moments that matter most — turning a difficult guest situation into a lasting reason to return

• 8+ years of hospitality leadership as a GM or equivalent at a hotel, resort, or lifestyle property
• A genuine love for building team culture — people trust you, follow you, and grow under your leadership
• Operational discipline and a natural ability to create structure that serves both the team and the guest
• Experience with weddings, events, or high-touch hospitality programming is a real plus
• A communication style that is clear, direct, and human — with ownership, your team, and your guests
• Genuine enthusiasm for working closely with an engaged ownership group and a collaborative leadership dynamic
• A grounded, accountable approach to leadership — you take ownership of outcomes and always bring solutions to the table
• Calm under pressure, decisive when it counts, and always focused on what is best for the guest and the team

More than experience or credentials, we are looking for someone who leads with genuine presence and accountability.

The right person for this role understands that great hospitality is built in the details — in how the team is treated, how standards are upheld consistently, and how problems are surfaced and solved with care. They communicate proactively, bring solutions with confidence, and take as much pride in a well-run Tuesday as in a flawless Saturday wedding.

Callicoon Hills is a founder-led property. Ownership is present, accessible, and deeply invested in the property's success. We are looking for a GM who sees that as an asset — someone who values a direct, trust-based relationship with ownership and understands that transparency and collaboration are what make this kind of environment thrive.

If that reflects how you lead, we'd love to connect.

Why Callicoon Hills

You will have real autonomy, real access to decision-makers, and a real opportunity to put your stamp on a property with genuine character and a loyal following.

What we offer in return is simple: trust, support, and a team that wants you to succeed. We will invest in you, listen to you, and give you the tools to do your best work. In exchange, we ask for the same.