Property Management Field Trainer

About the role

At Hillpointe, you'll be part of a dynamic, innovative team that has tangible impacts on day-to-day operations and contributes directly to overall success.

Responsibilities

• Improve Leasing & Sales Skills
  • Coach teams on lead management, follow‑up, communication, and closing.
  • Model strong leasing behaviors and identify opportunities for improvement.
• Elevate the Customer Experience
  • Train associates to deliver consistent, engaging tours.
  • Reinforce storytelling, product knowledge, and personalized service.
• Strengthen Processes & Standards
  • Ensure policies and procedures are followed.
  • Coach healthy, repeatable habits that drive consistent execution.
• On‑Site Coaching
  • Visit properties regularly to observe real interactions and provide in‑the‑moment feedback.
  • Support teams during lease‑ups, transitions, or performance challenges.
• New Hire Onboarding
  • Lead in‑person onboarding focused on service standards, systems, communication, and leasing fundamentals.
  • Build a confident foundation for new associates.
• Ongoing Development
  • Provide refreshers, role‑plays, and skill‑building sessions.
  • Encourage curiosity, growth, and continuous improvement.
• Document & Communicate Insights
  • Track progress, identify trends, and share needs with leadership.
• Collaborate With Operations & L&D
  • Align training with business goals and support new initiatives.

Qualifications

• Must be located in central Florida, ideally in the Orlando or Jacksonville area and be willing to travel up to 80%.
• 2+ years of property management experience.
• Strong leasing, customer service, and communication skills.
• Curious, outgoing, process‑oriented, and open to feedback.
• Enjoys teaching and helping others improve.

Physical Requirements

• Ability to travel up to 80% of the time, including driving between properties and occasionally staying overnight, depending on region coverage.
• Ability to lift, carry, and transport training materials or equipment, typically up to 15–20 lbs.

Work Environment

• Frequent on‑site visits to leasing offices and model units.
• Working alongside onsite teams in real time.
• Observing actual prospect interactions, tours, and leasing workflows.
• Hands-on coaching; this is not a “behind the desk” role.