Training and Development Specialist

Chicago-based property management company specializing in multifamily real estate, including market-rate, mixed-income and affordable housing properties. Known for our professionalism, operational excellence, and entrepreneurial mindset, Ansonia is a growing organization where people and performance truly matter.

Seeking a self-motivated property management professional to join us as our first Training & Development Specialist. In this role, you’ll propel our growth by refining and implementing processes across the company that continuously improve operational performance. The successful candidate will enjoy being “in the field” teaching and coaching site personnel, working at a fast pace and building systems that reinforce uniform practices across the portfolio.

This is not an “ivory tower” training role. Approximately half your time will be spent at properties, working side-by-side with site teams delivering hands-on training, reinforcing protocols, and identifying opportunities for improvement. The remaining time will be split between the corporate office and remote work, focused on protocol development, training design and collaborating with leadership. The Training & Development Specialist will play a critical role leading talent development.

You’ll be responsible for onboarding new employees and for managing and overseeing Ansonia’s leasing floaters, including their training and ongoing professional development.

• Design, refine, and continuously improve operational protocols for residential property management teams, with a primary focus on market-rate properties.
• Develop comprehensive training programs, manuals, playbooks, and job aids aligned with Ansonia’s standards, culture, and entrepreneurial operating model.
• Build structured 90-day onboarding and training plans for all new office-based hires.
• Integrate affordable housing requirements (Section 8, tax credit) into training programs as appropriate.
• Ensure training programs align with company goals, compliance requirements, and industry best practices.
• Deliver hands-on, asset-specific training for leasing, management, and administrative staff.
• Observe daily operations to ensure protocols are properly implemented and reinforced.
• Identify gaps, inefficiencies, and training needs by working directly alongside site teams.
• Support new hires on their first day, ideally being onsite to ensure a strong, consistent onboarding experience.
• Provide one-on-one and group coaching to property managers, assistant managers, and leasing staff. Develop leadership and professional development training for managers and regional leadership. Promote a culture of accountability, professionalism, curiosity, and continuous improvement. Support Regional Managers in diagnosing operational challenges and collaborate with them and the Director of Operations to develop practical, scalable solutions.

• Bachelor's degree in business administration, Property Management, Human Resources, or a related field
• Minimum 5+ years of residential property management experience (Community Manager or Trainer preferred) with a strong emphasis on market-rate properties.
• Proven experience developing, implementing, and delivering training programs and coaching colleagues.

• Highly self-directed, motivated, and comfortable operating without micromanagement.
• Strong organizational skills with the ability to manage multiple initiatives simultaneously.
• Excellent communication and presentation skills, both one-on-one and in group settings.
• Aptitude for coaching and constructive teaching.
• Analytical mindset with the ability to identify patterns, root causes, and scalable solutions.
• Experience overcoming resistance and driving adoption of new processes.
• Able to balance empathy with accountability.