Senior Software Developer I
Lessen
Software Engineering
Chicago, IL, USA
Posted on Jan 29, 2026
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.
This role is based in Chicago, working in the office on Monday, Tuesday and Thursday.
Job Summary
The Senior Software Developer supports the Product and Technology Department by managing day-to-day activities within the organization's software development function. Senior Software Developer is part of an agile development team building and working on enterprise-grade software. Senior Software Developer is involved in all areas of development, from design to development to testing. They lead a small team of Software Developers.
What You’ll Do
- Oversee the work of a team responsible for designing, building, testing, deploying, maintaining, and supporting applications or systems software.
- Work to establish functional requirements and reviews solutions to ensure organizational needs are met.
- Select and oversee implementation of one or more software development methodologies.
- Develop short- and long-term product roadmaps to ensure continuous improvement of software.
- Document and demonstrate solutions by developing documentation, flowcharts, layouts, diagrams, charts, code comments and clear code.
- Prepare and install solutions by determining and designing system specifications, standards and programming
- Improve operations by conducting system analysis, recommending changes in policies and procedures
- Protect operations by keeping information confidential
- Mentor junior developers
- Keep up to date on the newest technological innovations in the field and be ready to apply relevant innovations.
- Optimize new and existing applications.
- Foster a positive team environment
- Ensure confidentiality of internal and external data
- Perform ad-hoc projects and other duties as assigned
What You'll Need
- Comprehensive understanding of object-oriented and service-oriented application development techniques and theories
- Solid understanding of relational database design and querying concepts
- Exposure to Microsoft .NET development using C#, or JAVA or other major languages
- Exposure to web development using HTML5, CSS and JavaScript
- Familiar with Design Pattern, algorithm
- Knowledge of client/server application development
- Knowledge of agile development methodologies
- Knowledge of unit testing theory
- Experienced with source control management systems and continuous integration/deployment environments
- Experienced with debugging, performance profiling and optimization
- Internally motivated, able to work proficiently both independently and in a team environment
- Strong communication skills with both internal team members and external business stakeholders
- Strong initiative to find ways to improve solutions, systems, and processes
- Bachelor's degree in Computer Science, or with equivalent professional experience
- Fluent in English and Mandarin preferred
- 5+ years of experience as a software developer
- Hands-on experience building and deploying AI/ML features in production systems
- Familiarity with real-world use cases (prediction, NLP, vision, recommendation, anomaly detection)
- Ability to translate business problems into AI solutions
Minimum Qualifications
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.
