Field Trainer

Most property management trainers sit in a corporate office and build slide decks. This role is different. Hillpointe puts its Field Trainer on the ground, inside leasing offices, watching real tours happen in real time and coaching associates right after the prospect walks out the door.

Hillpointe develops and manages market-rate workforce housing across the Sun Belt. They control the full development cycle in-house, from land acquisition through construction and asset management, which means their leasing teams carry real weight. Traffic converts or it doesn't. This trainer's job is to make sure it does.

What This Role Actually Looks Like

Expect to spend most of your time on-site at properties, not behind a screen. You'll observe leasing consultants during actual prospect interactions, then give direct, specific feedback. You'll run onboarding for new hires, covering leasing fundamentals, service standards, and systems from day one. During lease-ups or performance challenges, you'll be the person leadership sends in.

The coaching work covers the full leasing cycle: lead management, follow-up cadence, tour delivery, objection handling, and closing. You'll identify where the process breaks down for individual associates and build repeatable habits that stick. Role-plays, refreshers, and in-the-moment observations are standard tools here.

You'll also document what you're seeing across properties and report trends back to operations and the learning and development team. If a particular site has a closing rate problem, you'll surface it with context, not just a number.

Travel is a real part of this job. Up to 75% of your time involves driving between properties, with occasional overnight stays depending on your region. This is not a role for someone who wants a predictable desk schedule.

What You Bring

• At least two years of hands-on property management experience, with strong leasing skills you can teach, not just demonstrate
• Real comfort with direct feedback, both giving it and receiving it
• A process-oriented mindset that can still flex when a site has its own rhythm
• Genuine interest in helping people improve, not just checking training boxes
• Ability to travel extensively throughout your assigned region

The candidates who excel here are typically former leasing managers or assistant managers who got results on-site and now want to scale that impact across multiple properties. They're specific in their coaching, not vague. They can show a consultant exactly how to reframe a price objection, not just tell them to "be more confident."

One honest note: the travel demand is high. If your region spans multiple markets, consecutive days on the road are likely. The upside is that this role builds a rare skill set. Field trainers who perform well often move into regional operations, training director positions, or broader L&D leadership as a company scales its portfolio.