Director of Training

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A privately held, national student housing organization is seeking a Director of Training to lead training strategy and field support across a multi‑property portfolio. This role partners closely with operations, sales, systems, and leadership teams to drive consistency, performance, and operational excellence at the property level.

Key Responsibilities

• Lead onboarding, ongoing education, and compliance training for field and corporate teams using a learning management platform
• Develop and maintain policies, procedures, toolkits, playbooks, and self‑service training resources
• Identify operational gaps and risks; implement training, documentation, and best‑practice solutions
• Oversee field‑based support functions and temporary operations support resources
• Partner with regional and senior leadership to ensure operational consistency and policy adherence
• Provide hands‑on training and operational support during lease‑ups, transitions, staffing gaps, and performance recovery
• Collaborate cross‑functionally with Operations, Sales, Accounting, Systems, and HR
• Support systems training and process rollouts (property management software experience required)

Ideal Background

• 5+ years of experience in student housing operations, with at least 2 years in a supervisory or leadership role
• Proven experience developing and delivering training programs across a multi‑property portfolio
• Strong working knowledge of leasing, AR/AP, and property‑level financial operations
• Experience with Entrata or similar property management systems strongly preferred
• Bachelor’s degree or equivalent professional experience

Additional Details

• Hybrid role based in Chicago (in‑office Monday-Thursday, remote Fridays) with 25% travel required
• Comprehensive benefits package including PTO, holidays, 401(k) with company match, and more

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