Machine Learning Engineer II
Lessen
| Company | Lessen |
| Category | Engineering |
| Location | Chicago |
| Remote | Hybrid |
| Employment | Not stated |
| Level | Not stated |
| Salary | USD 108k–136k |
| Posted | 30 May 2026 |
| Last verified | 30 Jul 2026 |
| Source | Employer career page (lever) |
Description
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.
The Machine Learning Engineer II role is part of the Technology Team, which is responsible for providing industry-leading machine learning-based tools or processes to the Company, which provide a competitive advantage and efficiency. You will work closely with cross-functional teams to build intelligent systems that solve real-world problems using machine learning, deep learning, and data science techniques.
This is a hybrid position, Tuesday and Thursday in the office.
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