Director of Operations & Transitions

Trailborn Hotel Management LLC•New York, NY

About The Position

The Director of Operations & Transitions plays a critical role in ensuring the seamless onboarding, transfer, and launch of hotels throughout the Trailborn portfolio. This includes acquisitions, divestitures, new openings, operator transitions, and enterprise‑wide operational initiatives. The role partners closely with Castle Peak Holdings, incoming/outgoing operators, brand partners, and internal Trailborn departments to protect operational continuity, uphold Trailborn standards, and deliver exceptional guest and team member experience. Essential Functions Hotel Transitions, Openings & Operational Integration Lead and coordinate all hotel transitions critical paths —including acquisitions, divestitures, openings, and operator changes—serving as the primary point of contact throughout the process. Develop and execute transition plans across operations, people, systems, brand standards, financial processes, and training, including clear handover processes and timelines aligned with Trailborn expectations. Support onboarding and training of new hotel teams and operators, including transfer of SOPs, system access, brand guidelines, contracts, vendor relationships, and reporting requirements to ensure full alignment with Trailborn standards. Partner with HR to ensure effective employee communication, staffing continuity, compliance, cultural alignment, and required training during transitions. Identify risks early, resolve issues quickly, and maintain clear communication regarding status, milestones, timelines, decisions, and cross‑functional alignment. Facilitate the setup, training, and validation of property distribution systems (CRS, PMS, GDS, OTAs, brand.com) while ensuring full alignment with Trailborn and brand standards, including oversight of PIP requirements, QA audits, and overall operational readiness. Operational Excellence Author, standardize, and maintain Trailborn’s operational SOPs across rooms, F&B, maintenance, guest services, finance, and technology to support consistent operational alignment. Partner cross‑functionally to ensure SOPs, workflows, and training materials support operational excellence and alignment across rooms, F&B, maintenance, guest services, finance, revenue, and IT. Implement consistent operational execution frameworks across the portfolio to ensure full alignment with Trailborn standards. Incorporate best practices identified during openings, transitions, operator onboarding, and training cycles to maintain ongoing alignment. Guest Experiences Analyze guest satisfaction (GSS) performance and create SMART action plans for operators to improve service, cleanliness, and overall guest experience. Partner with property and corporate teams to identify root causes, set measurable targets, and ensure continuous improvement while maintaining targeted benchmarks. Reporting & Analytics Develop and maintain reporting tools, standardized templates, and transition dashboards to track performance, readiness, and risk. Provide analytical insights to support decision-making and to evaluate post-transition success, stakeholder feedback, and operational outcomes. Conduct operational assessments and financial/efficiency evaluations, similar to consultant‑level assessments in the industry. Enterprise Systems Support deployment, training, and adoption of enterprise systems (PMS, POS, accounting, analytics, and operational platforms). Coordinate system cutovers, permissions, workflows, and brand‑required configurations. Ensure accurate integration with distribution systems and digital channels, including CRS, PMS, GDS, OTAs, and marketing systems. Special Projects Lead and support special initiatives across the organization, such as portfolio‑wide audits, operational enhancement programs, technology rollouts, and brand initiatives — ensuring cross‑functional alignment throughout execution. Drive cross‑functional collaboration and ensure deadlines, resources, and strategic goals are achieved with organizational alignment at every stage.

Requirements

Experience in hotel operations, asset management, consulting, transitions, or management company environments strongly preferred.
Demonstrated project management capability with strong coordination and communication skills, and experience managing hotel operations through construction or renovation.
Understanding of hotel operations, labor considerations, enterprise systems, and Marriott standards (or ability to learn quickly).
Ability and willingness to travel as needed to support hotel openings, transitions, on‑property training, and hands‑on operational alignment, consistent with broader industry transition roles.

Responsibilities

Lead and coordinate all hotel transitions critical paths —including acquisitions, divestitures, openings, and operator changes—serving as the primary point of contact throughout the process.
Develop and execute transition plans across operations, people, systems, brand standards, financial processes, and training, including clear handover processes and timelines aligned with Trailborn expectations.
Support onboarding and training of new hotel teams and operators, including transfer of SOPs, system access, brand guidelines, contracts, vendor relationships, and reporting requirements to ensure full alignment with Trailborn standards.
Partner with HR to ensure effective employee communication, staffing continuity, compliance, cultural alignment, and required training during transitions.
Identify risks early, resolve issues quickly, and maintain clear communication regarding status, milestones, timelines, decisions, and cross‑functional alignment.
Facilitate the setup, training, and validation of property distribution systems (CRS, PMS, GDS, OTAs, brand.com) while ensuring full alignment with Trailborn and brand standards, including oversight of PIP requirements, QA audits, and overall operational readiness.
Author, standardize, and maintain Trailborn’s operational SOPs across rooms, F&B, maintenance, guest services, finance, and technology to support consistent operational alignment.
Partner cross‑functionally to ensure SOPs, workflows, and training materials support operational excellence and alignment across rooms, F&B, maintenance, guest services, finance, revenue, and IT.
Implement consistent operational execution frameworks across the portfolio to ensure full alignment with Trailborn standards.
Incorporate best practices identified during openings, transitions, operator onboarding, and training cycles to maintain ongoing alignment.
Analyze guest satisfaction (GSS) performance and create SMART action plans for operators to improve service, cleanliness, and overall guest experience.
Partner with property and corporate teams to identify root causes, set measurable targets, and ensure continuous improvement while maintaining targeted benchmarks.
Develop and maintain reporting tools, standardized templates, and transition dashboards to track performance, readiness, and risk.
Provide analytical insights to support decision-making and to evaluate post-transition success, stakeholder feedback, and operational outcomes.
Conduct operational assessments and financial/efficiency evaluations, similar to consultant‑level assessments in the industry.
Support deployment, training, and adoption of enterprise systems (PMS, POS, accounting, analytics, and operational platforms).
Coordinate system cutovers, permissions, workflows, and brand‑required configurations.
Ensure accurate integration with distribution systems and digital channels, including CRS, PMS, GDS, OTAs, and marketing systems.
Lead and support special initiatives across the organization, such as portfolio‑wide audits, operational enhancement programs, technology rollouts, and brand initiatives — ensuring cross‑functional alignment throughout execution.
Drive cross‑functional collaboration and ensure deadlines, resources, and strategic goals are achieved with organizational alignment at every stage.