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Property Manager Trainee Jobs in Massachusetts (NOW HIRING)

Progressive

Claims Adjuster Trainee

Woburn, MA · Hybrid

$59K - $63K/yr

... managing the claims process from start to finish. You'll have the support of a collaborative team ... We'll also teach you the insurance stuff - providing in-depth training on property damage and ...

Progressive

Claims Adjuster Trainee

Canton, MA · Hybrid

$59K - $63K/yr

... managing the claims process from start to finish. You'll have the support of a collaborative team ... We'll also teach you the insurance stuff - providing in-depth training on property damage and ...

Progressive

Claims Adjuster Trainee

Westborough, MA · Hybrid

$59K - $63K/yr

... managing the claims process from start to finish. You'll have the support of a collaborative team ... We'll also teach you the insurance stuff - providing in-depth training on property damage and ...

Velox Valuations LLC

Staff Appraiser

Lunenburg, MA · On-site

Supervisor-Trainee Program * UAD 3.6 Ready with Training & Support Our goal is to achieve a ... Efficient time management & results driven * Strong communication skills with attention to detail

Ecolab Inc.

Pest Control Technician

Needham, MA

$24/hr

... property from the damaging effects of pests. Focused exclusively on commercial pest solutions, we ... As a Pest Control Technician Trainee, you'll be at the forefront of protecting public health and ...

Ecolab Inc.

Pest Control Technician

Needham Junction, MA · On-site

$24/hr

... property from the damaging effects of pests. Focused exclusively on commercial pest solutions, we ... As a Pest Control Technician Trainee, you'll be at the forefront of protecting public health and ...

Ecolab

Pest Control Technician

Needham, MA · On-site

$24/hr

... property from the damaging effects of pests. Focused exclusively on commercial pest solutions, we ... As a Pest Control Technician Trainee, you'll be at the forefront of protecting public health and ...

Ecolab Inc.

Pest Control Technician

Framingham, MA · On-site

$19.25 - $24.50/hr

... property from the damaging effects of pests. Focused exclusively on commercial pest solutions, we ... Ecolab is seeking a Pest Control Technician Trainee to join our team in [City, State - if ...

Ecolab Inc.

Pest Control Technician

Framingham, MA

$19 - $24.50/hr

... property from the damaging effects of pests. Focused exclusively on commercial pest solutions, we ... Ecolab is seeking a Pest Control Technician Trainee to join our team in [City, State - if ...

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Property Manager Trainee information

What is a property manager trainee?

A Property Manager Trainee is an entry-level professional who is learning how to oversee and manage residential or commercial properties. Under the guidance of experienced property managers, trainees gain hands-on experience in areas like tenant relations, property maintenance, rent collection, leasing, and compliance with housing laws. The role is designed to prepare individuals for a full property manager position by providing training in property operations, customer service, budgeting, and problem-solving skills. Trainees often assist with day-to-day tasks while receiving mentorship and on-the-job training.

What are the key skills and qualifications needed to thrive as a property manager trainee?

To thrive as a Property Manager Trainee, you need a basic understanding of property management principles, strong organizational skills, and often a high school diploma or associate degree. Familiarity with property management software, Microsoft Office, and knowledge of local real estate regulations are commonly expected. Excellent communication, problem-solving, and customer service skills help you build positive relationships with tenants and property owners. These abilities are essential for efficiently handling daily operations, resolving issues, and ensuring tenant satisfaction in a fast-paced environment.

What are some common challenges faced by property manager trainees during their first year, and how can they overcome them?

Property Manager Trainees often encounter challenges such as balancing multiple priorities, learning to handle tenant concerns diplomatically, and becoming familiar with property management software. Adapting to the fast-paced environment and responding to maintenance emergencies can also be demanding. Success in the first year often relies on strong organizational skills, seeking mentorship from experienced colleagues, and actively participating in training sessions to build confidence with processes and systems. Building relationships with tenants, vendors, and team members is essential for smoothing day-to-day operations and growing professionally.

How do you get into property management with no experience?

Property Manager Trainees often start by gaining basic knowledge of real estate and property operations through online courses or certifications. Entry-level roles may require strong communication and organizational skills, and some employers offer on-the-job training to develop industry-specific knowledge and management skills.

Is it easy to get hired as a property manager trainee?

Getting hired as a property manager trainee is generally achievable for candidates with strong communication skills, basic knowledge of real estate or property management, and a willingness to learn. Employers often look for relevant education or experience in customer service or administration, and some positions may require a valid driver's license or certification. Entry-level roles can have competitive application processes, but with proper preparation, opportunities are accessible.
Property Manager Trainee jobs near you
Infographic showing various Property Manager Trainee job openings in Massachusetts as of August 2026, with employment types broken down into 90% Full Time, 9% Part Time, and 1% Contract. Highlights an 81% Physical, 2% Hybrid, and 17% Remote job distribution.

Claims Adjuster Trainee

Progressive

Woburn, MA • Hybrid

$59K - $63K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 2 days ago

Key responsibilities

  • Learn how to help customers get back on the road after an accident by assisting with claims over the phone.

  • Manage the claims process from start to finish, including determining coverage and liability, interviewing involved parties, and partnering with appraisers to manage vehicle repairs.

  • Negotiate with customers and other insurance carriers to resolve claims.

Progressive Insurance rating

8.6

Company rating: 8.6 out of 10

Based on 601 frontline employees who took The Breakroom Quiz

96th of 315 rated insurance

Job description

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first step to Destination: Progress.

As a claims adjuster trainee, you’ll learn how to help customers get back on the road after an accident. This is not a field position, which means you’ll be building relationships with customers over the phone. In a fast-paced environment, you’ll learn how to resolve a full case load of claims efficiently while managing the claims process from start to finish. You’ll have the support of a collaborative team and ongoing coaching from leaders. We’ll also teach you the insurance stuff – providing in-depth training on property damage and insurance contracts so you can confidently and independently adjust claims.

This is a hybrid role, which means you’ll work in-office two days that are selected by local leadership and choose where you want to work the other three days, whether that’s at home or in the office, for a period of 12 months. After that period, the days you’ll be expected to report to an office for important meetings, training, and collaboration will vary based on business need. In this hybrid work environment, you’ll be supported by your leaders and tenured colleagues to develop relationships, establish connections, and share practices that are important to your development. If you prefer an in-office environment, you’re welcome to work in the office as often as you would like.

You must reside within 30 miles of Progressive's Canton, MA,  Westborough, MA or Woburn, MA Claims office at: 250 Royall St., Canton, MA 02021,  2000 W. Park Dr #110, Westborough, MA 01581, or 300 Unicorn Park Dr., Woburn, MA 01801

Duties & responsibilities (upon completion of training)

  • Determine coverage
  • Determine liability (who’s at fault for the damages)
  • Interview customers, claimants, and witnesses
  • Partner with appraisers/estimators to manage vehicle repairs
  • Negotiate with customers and other insurance carriers and resolve claims

Must-have qualifications

  • Three years of work experience OR
  • Bachelor’s degree OR
  • Two years work experience and an associate degree

Schedule: 

  • Training Schedule: Monday-Friday 8:30am-5:30pm
  • Work Schedule: Monday-Friday 8:00am-5:00pm and 9:00am-6:00pm, based on business need, which we will cover while you're in training.

Location: Canton, MA,  Woburn, MA or Westborough, MA. You must reside within 30 miles of Progressive's Canton, MA,  Westborough, MA or Woburn, MA Claims office at: 250 Royall St., Canton, MA 02021,  2000 W. Park Dr #110, Westborough, MA 01581, or 300 Unicorn Park Dr., Woburn, MA 01801

Compensation 

  • $59,500 - $63,500/yearly
  • Gainshare annual cash incentive payment up to 16% of your eligible earnings based on company performance

Benefits

  • 401(k) with dollar-for-dollar company match up to 6%
  • Medical, dental & vision, including free preventative care
  • Wellness & mental health programs
  • Health care flexible spending accounts, health savings accounts, & life insurance
  • Paid time off, including volunteer time off
  • Paid & unpaid sick leave where applicable, as well as short & long-term disability
  • Parental & family leave; military leave & pay
  • Diverse, inclusive & welcoming culture with Employee Resource Groups
  • Career development & tuition assistance
This position will be posted for a minimum of 2 business days or until a sufficient candidate pool has been collected

Energage recognizes Progressive as a 2025 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

For ideas about how you might be able to protect yourself from job scams, visit our scam-awareness page at https://www.progressive.com/careers/how-we-hire/faq/job-scams/

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