Lessen21d ago

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From $50/yr

Experienced Field Maintenance Technician (3+ Years Required)

United States·ChicagoRemoteFull Time Employeemid

OperationsMaintenance TechnicianTrades & Skilled LaborSkilled Trades & Field Services

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Quick Summary

Overview

Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.

Technical Tools

OperationsMaintenance TechnicianTrades & Skilled LaborSkilled Trades & Field Services

Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.

Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.

Pay range starting at $23 hr - $27 hr.

Lessen is seeking an experienced, solution-oriented Field Maintenance Technician with a minimum of 3 years of verifiable, hands-on experience in property management maintenance or a related trade. You will own your work orders, manage budgets, and oversee comprehensive maintenance for properties in our portfolio. We prioritize quality, over quantity, to provide excellent customer service to our clients. We are looking for forward thinking, and solution-oriented techs who want to grow with our brand as we expand our locations nationally.

• Quarterly Bonus! You will be eligible for a quarterly discretionary bonus of up to 5% of quarterly earnings

• No on-call! Weekday schedule!

• The company will provide a tool/equipment allowance of $50 per month

• The company will provide a cell phone allowance of $50 per month

• Company fleet vehicle and fuel card

• Growth opportunities into Lead Technicians and Field Maintenance Managers

• Provided OSHA training

• Competitive hourly rate and corporate-level benefits!

Respond, as directed, promptly and professionally to skilled maintenance and repair requests.

Ensure work is performed in a timely and professional manner

Assist with scheduling, overseeing, and communicating with contractors to obtain bids and checking work for completeness

Purchase maintenance supplies as needed for the property

Perform preventive maintenance and comprehensive repairs in the areas of plumbing, appliances, pool equipment, carpentry, sheetrock, exterior and basic electrical issues.

Ability to travel within your region: this position is based 100% in the field.

3+ years of verifiable, hands-on experience in property management maintenance, other building maintenance, or a related trade.

Demonstrated Proficiency in diagnosing, troubleshooting, and performing comprehensive repairs across all standard trades, plumbing, electrical, appliance, carpentry.

Proven ability to manage and complete independent work orders, budget time/materials, and communicate effectively with contractors/clients.

Current driver’s license and automobile insurance.

Must be able to lift, push, pull 50lbs regularly; up to 75lbs occasionally; and 75+lbs with assistance.

Holding a current or previous plumbing license is a plus.

#IND2

Location & Eligibility

Where is the job

Chicago, United States

Remote within one country

Who can apply

Listed under

United States

Listing Details

Posted: April 13, 2026
First seen: April 13, 2026
Last seen: May 5, 2026

Posting Health

Days active: 21
Repost count: 1
Trust Level: 49%
Scored at: May 5, 2026

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Lessen

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Lessen is a tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.

Employees

3k+

Founded

2019

Domain

lessen.com

Jobs

View 56 jobs

View company profile

Salary

From $50

per year