Maintenance Supervisor in Training - Addison at Wyndham

Most apartment communities separate their maintenance leadership from hands-on work. Weinstein Properties takes a different approach: they develop supervisors from within the work itself, which is why this role exists. The Maintenance Supervisor in Training position at Addison at Wyndham in Glen Allen puts you on the floor with a working supervisor and a full team, building toward a leadership seat rather than being dropped into one unprepared.

What This Role Actually Looks Like Day to Day

You'll spend your time split between doing and directing. Some mornings that means diagnosing an HVAC issue in a resident's unit; others it means coordinating vendor scheduling or reviewing the work order queue to make sure turns are moving on time. The hands-on expectation is genuine here. This isn't a desk role with occasional walkthroughs. You'll work alongside the team on repairs across HVAC, electrical, plumbing, appliances, carpentry, drywall, pool maintenance, and exterior structural work. You'll also share on-call rotation with other team members, so nights and weekends will come up. That's worth knowing going in.

The training component means you'll shadow and work under an experienced supervisor while gradually taking on more coordination responsibilities. Weinstein owns and manages all of its properties in-house rather than operating under third-party management, which tends to create more consistent standards and clearer internal career paths. Flexibility to transfer to another community as you advance is part of the arrangement.

Compensation starts at $26 per hour depending on experience, with a $150 weekly on-call bonus regardless of call volume, an additional holiday on-call bonus, a quarterly performance bonus with up to $1,110 potential, and a $1,500 sign-on bonus (details discussed during the interview). Benefits include rent discount, health, dental and vision, 401k, PTO, paid holidays, and birthday time off.

Who Fits This Role Well

• At least 4 years of trade experience with hands-on work in HVAC, plumbing, electrical, and general building maintenance
• At least 1 year in a lead, assistant supervisor, or supervisory maintenance role at an apartment community
• EPA/CFC Refrigerant certification (Type I and II, or Universal) is required before starting
• Comfortable using software to manage work orders, schedule turns, order supplies, and communicate with the team
• Valid driver's license, personal transportation, and your own tools
• DMV check and background check required

What separates strong candidates here isn't just technical range. It's the combination of trade competence with genuine comfort talking to residents. Maintenance supervisors at the community level are often the face of the property when something goes wrong. Residents remember how a repair interaction felt, not just whether it got done. If you can fix the problem and leave the resident feeling heard, you'll thrive in this kind of role. If you've been a strong tech who's ready to grow into leading others, this training structure is a real on-ramp, not just a title.