Internship

Sorry, this job was removed at 06:20 p.m. (CST) on Tuesday, May 19, 2026
Chicago, IL, USA
Hybrid
Cloud • Real Estate • Software • PropTech
Help us revolutionize real estate services.
The Role

Lessen is now taking applications for our Summer Internship Program!

About Lessen

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.

Program Overview

The Lessen 2026 Summer Internship Program is a 6-week, paid experience designed for high-potential students seeking real-world exposure to business innovation. Interns will work in small, collaborative teams, receive mentorship from senior leaders, and develop solutions tied directly to Lessen’s strategic priorities.

This is not a traditional internship—participants will act as builders and problem-solvers, working to develop and commercialize new, revenue-generating initiatives leveraging Lessen’s platform, vendor network, and AI capabilities.

Why Join Lessen?

  • Accelerate Innovation: Work on real business opportunities that internal teams don’t have capacity to pursue
  • Hands-On AI Exposure: Apply AI concepts to real-world use cases
  • Executive Access: Engage directly with senior leadership and mentors
  • Collaborative Culture: Be part of a high-energy, team-driven experience

Program Details

  • Duration: 6 weeks (June – July 2026)
  • Schedule: ~30 hours per week

Location:

  • Scottsdale, AZ or Chicago, IL
  • Travel & lodging provided as needed

Who Should Apply?

We are seeking junior/senior undergraduates or recent graduates with interest in:

  • Product / Technology / Engineering
  • Finance / Accounting
  • Marketing / Business
  • Legal

Ideal candidates are:

  • Curious, analytical, and entrepreneurial
  • Strong problem-solvers with a bias for action
  • Comfortable working in a fast-paced, collaborative environment

What the Team is Saying

Jay Payne
Kirby Pumper
Maya Shea
Jay McKee
Jennifer Gordon
Trevon

Lessen LLC Compensation & Benefits Highlights

  • Leave & Time Off Breadth Time off is presented as generous, spanning paid holidays, sick time, bereavement leave, and paid volunteer time. For some roles, flexible or unlimited PTO adds additional latitude.
  • Healthcare Strength Core coverage includes medical, dental, and vision alongside mental‑health resources and FSAs. Pet insurance is also available, indicating breadth beyond standard medical plans.
  • Parental & Family Support Paid parental leave, family medical leave, childcare benefits, and onsite mother’s rooms are highlighted. These supports signal a family-oriented approach to benefits.

Lessen LLC Insights

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The Company
HQ: Scottsdale, Arizona
713 Employees
Year Founded: 1999

What We Do

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. To learn more, visit Lessen.com.

Why Work With Us

We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.

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Lessen LLC Teams

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Lessen Direct - A Mobile Technician Workforce
About our Teams

Lessen LLC Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.

Typical time on-site: 3 days a week
HQScottsdale, AZ
Chicago, IL
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