Director of Training & Systems

POSITION DESCRIPTION

Director of Training & Systems

Department: Training Reports To: Chief Operating Officer FLSA: Exempt

POSITION OVERVIEW

The Director of Training & Systems is a senior leadership role responsible for building and sustaining the operational knowledge infrastructure of the organization. This position owns the full employee development lifecycle, from onboarding and compliance training through leadership development and performance enablement, while serving as the internal champion for the technology platforms and operational systems that power day-to-day property management across the portfolio. Reporting directly to the COO, this role requires a dynamic leader who can design and deliver training programs that drive measurable performance improvement, build scalable systems that support a growing team, and champion the adoption of technology that makes the organization more efficient and competitive.

KEY RESPONSIBILITIES

Training & Development

• Build, implement, and continuously improve training programs for all staff levels, including onboarding, compliance, customer service, fair housing, leasing skills, and technical operations.

• Develop leadership development pathways to identify and grow internal talent for advancement opportunities across the portfolio.

• Evaluate training effectiveness through assessments, performance data, and employee feedback, adjusting programs based on what the data reveals.

• Oversee Learning Management System administration and content development in partnership with operations and regional leadership.

• Facilitate or coordinate monthly training sessions, workshops, and role-specific skill development programs across the organization.

• Provide leadership, guidance, and mentorship to the training team.

Policy Development & Management

• Draft, maintain, and communicate company policies and the employee handbook in alignment with applicable federal, state, and local employment laws.

• Ensure policies are written in plain language that is operationally practical and accessible to all staff levels.

• Partner with HR and legal resources to review and update policies as regulations, organizational needs, or operational standards evolve.

• Develop and maintain a policy communication framework that ensures awareness and accountability across the organization.

Systems & Technology Leadership

• Oversee the selection, implementation, and optimization of property management platforms and operational technology tools across the portfolio.

• Serve as the internal champion for technology adoption, leading change management efforts and training staff on new systems with a focus on sustained utilization.

• Develop and monitor KPIs related to system utilization, efficiency gains, and process improvement outcomes.

• Evaluate emerging property management technologies and recommend solutions that align with strategic growth objectives and operational needs.

• Partner with operations leadership to ensure systems support, rather than complicate, the day-to-day work of property managers and site teams.

Organizational Performance & Reporting

• Track and report on training completion rates, system adoption metrics, and performance improvement outcomes to the COO and leadership team.

• Identify systemic performance gaps across the organization and develop targeted training or process interventions to address them.

• Support the development of standardized operational workflows and SOPs that reinforce training content and create consistent execution across properties.

• Collaborate with regional and director-level leadership to align training priorities with portfolio performance goals on a quarterly basis.

QUALIFICATIONS

Required

• 5 years of progressive experience in training and development, organizational learning, change management, or a related people development function.

• Demonstrated experience building and executing training programs that produced measurable performance improvement.

• Proven track record of driving technology adoption and managing change across a distributed workforce.

• Strong leadership and people management skills, with experience developing and directing a team of training professionals.

• Exceptional written and verbal communication skills, with the ability to deliver content effectively across all levels of the organization.

• Experience developing or maintaining policy documentation, SOPs, or employee handbooks.

• Familiarity with Learning Management Systems and digital content development tools.

Preferred

• Progressive multifamily property management experience, strongly preferred. Direct experience as a property manager, regional manager, or equivalent role provides meaningful credibility with site teams and accelerates program design.

• Experience with AppFolio, Yardi, Grace Hill, or comparable property management and training platforms.

• Bachelor's degree in Business Administration, Organizational Development, Human Resources, or related field.

• Experience building or scaling people development programs in a growing organization.

• Track record of developing internal talent into promoted roles.

What We're Looking For

• The Director of Training & Systems is someone who believes the gap between a good team and a great one is almost always a knowledge and systems problem; who has the skills, the drive, and the creativity to close it.

• They are equally comfortable in front of a room training a group of leasing agents and behind a screen evaluating a new technology platform.

• This is a builder's role. The right candidate does not need things to already be in place to be effective; they thrive precisely because they are not.