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Maintenance Technician - North Port FL

Remote, USA Full-time Posted 2026-06-24

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.

Our Maintenance Technicians are responsible for conducting general maintenance and repairs on properties within our portfolio.

You will have the ability to “own” your work orders and have the freedom to manage your budget and schedule. You will be in the field working on an average of 5-6 work orders a day for general maintenance services. 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!

What You'll Do

  • Respond, as directed, promptly and professionally to work order 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 minor repairs in the areas of plumbing, appliances, pool equipment, carpentry, sheetrock, exterior and basic electrical issues
  • You Should Have

  • Ability to travel within your region: this position is based 100% in the field.
  • 3 years of previous experience in property management maintenance, other building maintenance or related trade.
  • Basic experience in all standard trades (plumbing, electrical, appliance, carpentry)
  • 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.
  • Additional Information

    Why Lessen:

    · Competitive compensation

    · Health, Dental, Vision, Life, Disability options

    · 401K retirement savings plan

    · Paid vacation, federal and floating holidays

    · Maternity/Paternity Pay

    · Career advancement opportunities

    · All the tools you'll need to be successful

    Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

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