Training Director Jobs in Boca Raton, FL (NOW HIRING)

Location:

Based out of Ft. Lauderdale, FL

Why Highmark Residential?

Because every position is considered critical to Highmark’s success and reputation, we take care to employ those who aspire to become the best in their field. Those who succeed at Highmark will do so because they enjoy an empowered, challenging, fulfilling, and financially rewarding workplace!

Why we need you:

The Regional Training Director drives operational excellence, cultural alignment, and talent development across a diverse portfolio of communities. Blending strategic oversight with hands-on execution, this role delivers high-impact training, coaching, and performance feedback both onsite and virtually. As a key partner to regional leadership, you’ll elevate frontline capabilities, foster a scalable learning culture, and ensure employees are equipped to deliver exceptional service. Success requires a strategic mindset, strong leadership, and a passion for growth and continuous learning.

What Highmark can do for YOU:

• Help you achieve your goals by continuous professional development and regular career progression sessions
• Competitive pay for the market
• Monthly bonus opportunities for all site associates
• 30% associate rent discount
• Medical, Dental & Vision benefits the 1st of the month following 30 days of full-time employment
• Company-provided life insurance, short term and long term disability coverage
• Flexible Spending accounts
• 401(k) eligibility after 90 days, with 4% Highmark match
• Professional Certification & Tuition reimbursement
• Vacation, Sick and Personal Time off available to use after 90 days
• 10 paid holidays
• Paid parental leave

Responsibilities include (but are not limited to):

Training Collaboration and Facilitation:

1. Lead engaging in-person and virtual training sessions that include leasing and sales, operations, compliance, and customer service/hospitality.
2. Effectively and consistently deploy nationally developed curriculum and software across regional portfolio.
3. Identify training needs and performance gaps through data analysis, feedback and collaboration with regional leadership.
4. Weigh in on curriculum updates and requested edits to ensure relevance and impact.
5. Oversee coordination of schedule to ensure timely, consistent delivery, engagement and impact.
6. Support team member compliance with Learning Management System (LMS) requirements and track completion metrics.

Leadership and Team Development:

1. Conduct onsite training evaluations and visits to assess performance, identify skill gaps and reinforce service standards.
2. Provide real-time coaching to property teams, modeling best practices and driving accountability across roles.
3. Customize and deploy corporate training programs for regional rollout, ensuring alignment with business goals and local needs.
4. Support implementation of leadership development, affordable housing training, and compliance initiatives to build bench strength and operational excellence.
5. Partner with Regional Managers, Regional Vice President, and Marketing to align training with strategic priorities and brand standards.
6. Serve as a trusted advisor to onsite team leaders, translating business needs into targeted learning solutions that elevate team performance.

Compliance and Cross-Functional Collaboration:

1. Stay current on industry trends, best practices, and regulatory changes impacting the property management industry, both locally and nationally.
2. Ensure all training programs meet legal and compliance standards across operational areas.
3. Build strong partnerships with Regional Managers, HR professionals, and subject matter experts to align training with business needs.
4. Collaborate with cross-functional teams to identify and address training gaps in customer experience, leasing and sales, maintenance, and compliance.

Work Environment:

1. Travel Expectations: Up to 50% travel across the assigned region to assess performance, deliver coaching and training, as well as support onsite teams.
2. Work Arrangement: Hybrid, depending on proximity to a regional office location.

Qualifications:

• High school diploma or equivalent - Bachelor’s degree preferred.
• 2+ years in training, learning & development, or property operations within multifamily housing.
• Proven experience leading training across dispersed teams; comfort with travel and field-based work.
• Strong facilitation skills—both in-person and virtual—with ability to engage and inspire diverse audiences.
• Demonstrated ability to motivate teams and foster a culture of learning and accountability.
• Knowledge of industry regulations, compliance standards, and multifamily best practices.
• Self-directed and highly organized, with a proven ability to manage time effectively and contribute meaningfully within team-based, cross-functional settings.
• Skilled in cross-functional collaboration, especially with regional operations and marketing teams.
• Excellent communication, coaching, and stakeholder management skills.
• Proficiency in managing a Learning Management System (LMS) and leveraging data to track training outcomes.
• Familiarity with Canva and basic instructional design principles for content creation and visual engagement.
• Proficiency in property management systems; Yardi experience preferred.
• Strong understanding of adult learning principles and training evaluation techniques.
• Knowledge of relevant regulations, affordable housing programs and compliance standards.
• Flexibility to travel within the region and to other locations as needed.
• Skilled in navigating complex conversations with empathy and awareness of cultural and regional nuances.
• Must be able to travel and incur expenses on a personal credit card.

#CORP

Req. ID: 2026-9508