Director, Training & Development

Collective Residential•Bethesda, MD

About The Position

Collective Residential is seeking a hands-on Director of Training & Development to build and lead learning across its property management companies. The role sets the learning strategy and personally designs, develops, and delivers programs, working without a dedicated team and drawing on subject matter experts across the business. Learning priorities should align with operational goals, employee development, technology adoption, and the evolving needs of the business, serving on-site teams and corporate functions. The Director owns technology training and adoption, supports operational centralization and acquisitions, and develops core multifamily, maintenance, leadership, and compliance training. The role also manages Collective’s training calendar, budget, learning tools, and Grace Hill LMS, and creates a centralized, accessible repository of learning materials. Training impact is measured through proficiency, time to productivity, technology adoption, and relevant operational outcomes, with programs continuously improved based on findings. The role requires travel to properties 10–15%; most training is delivered virtually. Compensation includes base salary and bonus potential, commensurate with experience. The company offers a comprehensive benefits package and an environment of continual growth and development.

Requirements

10+ years of experience in learning and development, training, or organizational development, including leading programs across multiple locations or business units.
Experience in multifamily or property management.
A track record of designing onboarding, systems or technology training, and leadership development programs.
Hands-on experience managing a learning management system (LMS).
Experience leading technology adoption and change management initiatives.
Comfort using data to identify skill gaps and measure training impact.
Strong facilitation, communication, and stakeholder management skills, with the ability to influence leaders at all levels.
Ability to travel 10–15% to properties; most training is delivered virtually.
Bachelor’s degree or equivalent combination of education and experience.

Nice To Haves

Grace Hill experience.

Responsibilities

Own the training strategy across Collective’s property management companies, aligning learning priorities with operational goals, employee development, technology adoption, and business needs.
Personally design, develop, and deliver training content, including needs assessment, instructional design, materials, facilitation, and evaluation.
Build role-specific onboarding programs for on-site employees, including structured learning plans, hands-on practice, manager check-ins, and proficiency assessments.
Deliver learning through live instruction, virtual sessions, short learning modules, field coaching, and peer learning.
Partner with operators and subject matter experts to capture expertise and co-deliver content while maintaining quality, consistency, and results.
Manage the training calendar, budget, and learning tools, and lay the groundwork for a train-the-trainer model.
Own technology training and adoption in partnership with IT, Innovation, Operations, and software providers.
Establish recurring office hours and ongoing learning opportunities to answer questions, reinforce training, troubleshoot workflow challenges, and identify knowledge gaps.
Translate redesigned processes into practical training, document responsibilities and handoffs between on-site and centralized teams, and prepare employees for centralization efforts.
Partner with HR and Operations to modernize on-site job descriptions to reflect technology, automation, centralized support, and resident service delivery changes.
Develop and maintain multifamily training programs covering leasing and sales, renewals, resident engagement, service recovery, delinquency management, financial fundamentals, and property operating procedures.
Coordinate maintenance and service-team training, including work-order management, preventive maintenance, unit turns, safety, and resident interactions.
Build leadership and career development programs covering coaching, communication, accountability, financial acumen, and people management.
Partner with HR, Legal, Compliance, and operational leaders to deliver required training, maintain completion records, and schedule refreshers.
Support acquisitions and property transitions by assessing training needs, introducing systems and operating standards, and delivering targeted onboarding and reinforcement.
Create and maintain a centralized learning and knowledge resource containing current SOPs, playbooks, recorded demonstrations, quick-reference guides, and FAQs.
Oversee Grace Hill, including content creation and selection, role-based assignments, reporting, vendor performance, and alignment with internal training priorities.
Identify performance and skill gaps through operational data, property visits, employee feedback, and leader input; distinguish training needs from process or system issues and coordinate solutions.
Measure training effectiveness through employee proficiency, time to productivity, technology adoption, and relevant operational outcomes, and use findings to improve programs.
Perform other duties as assigned.