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Field Trainer

Posted 2 months ago

OfficeJacksonville, FL

WHY HILLPOINTE? Hillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. Ranked at the top of NMHC's list of Builders and Developers, our team ensures best-in-class execution.

Built on its long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise, enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, procurement of building materials, asset management, and capital markets. This is more than just a job - it's a career-defining opportunity! 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.


FIELD TRAINER

Key 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:

  • 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 75% 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

#LI-Onsite

Job details
Workplace
Office
Location
Jacksonville, FL

Hillpointe is a fully integrated real estate development and investment management firm focused on workforce housing across the Sun Belt. Built on its principals’ long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, building materials procurement, asset management and capital markets. Hillpointe’s principals make significant and meaningful cash investments in each project.

Employees
400
Industry
Real Estate
Headquarters
Winter Park, Florida
Founded
2018
Company location
1031 W Morse Blvd, Suite 240, Winter Park, Florida 32789, US
Specialties
Real Estate, Real Estate Investment, Capital Management, Investment Strategy, Multifamily Housing, Single Family Housing, Apartments, and Workforce Housing

Key team members

Chip Wooten

Chip Wooten

Nick Everly

Nick Everly

Marcus Wiedower

Marcus Wiedower

Tyler Garner

Tyler Garner

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