Job Details

Position Summary

The Training and Engagement Assistant plays a critical role in supporting Oakwood Management Company's employee development, resident experience, community partnerships, and brand engagement initiatives. This position works closely with the Training and Engagement Manager to coordinate and deliver consistent, high-impact training and engagement programs. The role combines internal team development with outward-facing initiatives that enhance Oakwood's culture, resident satisfaction, and community presence.

Key Responsibilities

Training and Development (Primary Focus)

• Support the planning, organization, and delivery of all company training programs, including new hire onboarding, software systems, leasing best practices, Fair Housing, customer service, and leadership development.
• Facilitate or co-facilitate group training sessions, in-person workshops, and virtual webinars in an engaging and interactive manner.
• Assist in developing and updating training materials, including slide decks, printed guides, e-learning content, video tutorials, SOP documentation, and skill-building checklists.
• Track training progress and completion for new hires and existing employees; follow up on outstanding tasks and learning requirements.
• Review mystery phone and video shops; provide clear, constructive feedback and assist the manager in delivering performance coaching when necessary.
• Create job aids, one-pagers, and user-friendly tools for property-level team members to support process consistency and improve performance.
• Stay current on Oakwood systems such as Yardi, CRM IQ, Rent Café, and Revenue IQ, and help train staff on new features or updates as they roll out.
• Coordinate training logistics such as room set-up, materials preparation, calendar scheduling, and Teams link management.
• Identify gaps in operational knowledge or soft skills and recommend customized learning solutions for individuals or teams.
• Serve as a first point of contact for training-related questions and support requests, ensuring prompt and helpful assistance.

Oakwood Cares & Community Volunteering

• Assist in coordinating meaningful volunteer opportunities in partnership with local nonprofits.
• Organize event logistics, schedule dates, manage employee sign-ups, and send communications.
• May attend or supervise volunteer events at the manager's request to ensure smooth execution and employee engagement.

Resident Experience & Company Events

• Support initiatives designed to enhance the resident experience and drive renewal rates across properties.
• Respond to resident reviews rated 3 stars or below on behalf of the company in a professional, empathetic tone.
• Assist with company-sponsored resident events and help develop “Oakwood Experience” concepts.
• Identify opportunities for operational improvement based on resident feedback and support related training solutions.
• Help source and organize vendor partnerships to simplify event planning at the site level.

Partnerships & Brand Engagement

• Assist with maintaining Oakwood's network of brand partners that provide residents with exclusive offers, freebies, and events.
• Help create marketing collateral and communication materials to support these partnerships.
• Prepare digital or printed materials needed to promote vendor-sponsored experiences at properties.

Leasing & Sales Support

• Assist with reviewing leasing reports, occupancy trends, and sales performance data.
• Evaluate and score sales and customer service phone calls to assess quality and effectiveness.
• Contribute to internal leasing competitions and recognition programs that encourage performance and teamwork.
• Research AI leasing tools and assist in evaluating potential solutions to enhance the leasing process.

Required Skills and Qualifications

• Strong public speaking and group facilitation skills; must be comfortable leading in-person and virtual sessions
• High level of interpersonal communication and a “people person” mindset; must enjoy working across teams and personalities
• Highly organized and detail-oriented, with the ability to manage multiple priorities at once
• Strong written communication and documentation skills
• Positive, flexible, and self-motivated attitude with a willingness to learn
• Proficiency in Microsoft Office (Excel, Word, PowerPoint) and comfort learning new software systems
• Ability to work independently while collaborating with multiple departments
• Previous experience in training, leasing, resident services, hospitality, or property management is preferred

What Success Looks Like

The Training and Engagement Assistant supports the foundation of employee growth and resident satisfaction at Oakwood. Success in this role means delivering well-executed trainings, improving on-site team performance, driving resident engagement, and helping build a positive company culture where employees feel supported and residents feel at home.