Management Trainee (Deerfield Forest Condominium

Management Trainee (Deerfield Forest Condominium)

Natick, MA, USA

Posted Thursday, August 13, 2026 at 4:00 AM

At Winn Companies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 28 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact.

About the opportunity

Winn Companies is looking for a
Management Trainee to join our team at Deerfield Forest Condominium
, a 334-unit condominium complex housing community located in Natick, MA
.

In this role, you will assist the Property Manager with the daily operation of the assigned property and provide administrative support to develop the knowledge and skills needed to effectively manage a property. You will also complete special projects as assigned by direct supervisor.

The pay range for this role is $22.00-$24.00 per hour. The selected candidate will adhere to the following schedule:
Monday through Friday from 8:00AM to 5:00PM

Responsibilities:

• Provide administrative support to develop the knowledge and skills needed to effectively manage a property.
• Complete special projects as assigned by direct supervisor.
• Retain existing residents and increases resident satisfaction: ensure a positive move-in experience, provide continual excellent customer service, facilitate resident programs and services, assist with resident problems as they arise.
• Utilize property management system to collect/post and deposit rents and condo fees, assess resident charges or process refunds and completes activity related to vendor payments.
• Conduct a morning tour of the property, inspect apartments, follow up on outstanding work orders, close out completed work orders.
• Provide administrative support, including routing mail and maintaining resident and property files.

Requirements:

• High school diploma or GED equivalent.
• Minimum of 1 year of relevant work experience.
• Must have excellent customer service and willing to go up and beyond with residents who live in condos
• Experience with various computer systems, including Microsoft Office.
• Solid verbal and written communication skills.
• Excellent customer service and time management skills.
• Willingness to learn and be trained.
• Ability to exercise good judgment and apply initiative.
• Ability to multi-task in a fast-paced office environment.
• Ability to work with a diverse group of people and personalities.

Preferred Qualifications:

• Experience in property management.
• Experience with Yardi or Real Page property management software.
• Notary Public but can obtain after hire.

Benefits & Perks
Eligible full-time U.S. employees enjoy a competitive benefits package, including:

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options
• 401(k) with company match and company-paid life, AD&D, and long-term disability insurance
• Tuition reimbursement, professional development opportunities, and career growth resources
• Wellness programs, employee assistance resources, commuter benefits , and employee discount programs
• Flexible and hybrid work options for eligible positions

If you are a California Resident, please see our Notice of Collection here .

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.