How do employees rate Lessen?

Employees rate Lessen 2.2 out of 5 stars based on 179 anonymous reviews on Glassdoor.

How can I get a job at Lessen?

To get a job at Lessen, browse currently open positions and apply for a job near you. Once you get a positive response, make sure to find out about the interview process at Lessen and prepare for tough questions.

Do people recommend working at Lessen?

Overall, 23% of employees would recommend working at Lessen to a friend. This is based on 179 anonymously submitted reviews on Glassdoor.

How do job seekers rate their interview experience at Lessen?

42% of job seekers rate their interview experience at Lessen as positive. Candidates give an average difficulty score of 2.4 out of 5 (where 5 is the highest level of difficulty) for their job interview at Lessen.

How do employees rate the business outlook for Lessen?

14% of employees think that Lessen has a positive business outlook . This is based on anonymous employee reviews submitted on Glassdoor.

Working at Lessen

Lessen Snapshot

2.2

based on 179 ratings

23% would recommend to a friend

Jay McKee

26% approve of CEO

2 OfficesLocations

Life at Lessen

Company updates

Lessen

2mo

Lessen’s CEO, Jay McKee, has been named one of GlobeSt.’s Influencers in CRE Technology for 2026. Under Jay’s leadership, Lessen has grown into a national platform that brings together technology, AI, and operational excellence to transform a historically fragmented industry. Today, our solutions support real estate portfolios across more than 280,000 properties, delivering faster service, greater visibility, and more consistent outcomes. We are proud of the momentum our team continues to build and grateful to our employees whose work makes this impact possible every day. If you are interested in being part of a company shaping the future of real estate technology, we would love to connect. ...Show more

Lessen’s CEO, Jay McKee, has been named one of GlobeSt.’s Influencers in CRE Technology for 2026. Under Jay’s leadership, Lessen has grown into a national platform that brings together technology, AI, and operational excellence to transform a historically fragmented industry. Today, our solutions support real estate portfolios across more than 280,000 properties, delivering faster service, greater visibility, and more consistent outcomes. We are proud of the momentum our team continues to build and grateful to our employees whose work makes this impact possible every day. If you are interested in being part of a company shaping the future of real estate technology, we would love to connect.

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Lessen

2mo

Last week, we had the opportunity to celebrate Employee Appreciation Week at Lessen, recognizing the incredible people who power our success every day. From fun color-themed spirit days and swag giveaways to coffee bars, taco stands, and team photos across our offices and remote teams, it was a week full of connection and celebration. We also recognized 23 outstanding employees who exemplify Lessen’s core values and make a meaningful impact across the organization. At Lessen, we truly value our employees and are grateful for the dedication, teamwork, and pride they bring to their work each day. Their hard work is what makes our success possible, and we are proud to celebrate and thank them. ...Show more

Last week, we had the opportunity to celebrate Employee Appreciation Week at Lessen, recognizing the incredible people who power our success every day. From fun color-themed spirit days and swag giveaways to coffee bars, taco stands, and team photos across our offices and remote teams, it was a week full of connection and celebration. We also recognized 23 outstanding employees who exemplify Lessen’s core values and make a meaningful impact across the organization. At Lessen, we truly value our employees and are grateful for the dedication, teamwork, and pride they bring to their work each day. Their hard work is what makes our success possible, and we are proud to celebrate and thank them.

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Lessen

4mo

In December, our sales team gathered in Scottsdale for our FY26 Sales Kickoff—an energizing opportunity to come together, build connections, and align on what’s ahead. These moments matter: they give us space to collaborate, share ideas, and plan how we’ll support one another in the year to come. The week reinforced what makes this team special—smart, driven people working together toward shared goals. We’re heading into the new year energized and excited about what we’re building at Lessen....Show more

In December, our sales team gathered in Scottsdale for our FY26 Sales Kickoff—an energizing opportunity to come together, build connections, and align on what’s ahead. These moments matter: they give us space to collaborate, share ideas, and plan how we’ll support one another in the year to come. The week reinforced what makes this team special—smart, driven people working together toward shared goals. We’re heading into the new year energized and excited about what we’re building at Lessen.

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Lessen

5mo

2. Our founder and CEO, Jay McKee, was recently selected by Commercial Observer for their Power Proptech list — a recognition reserved for leaders driving the future of real estate technology. Jay earned that spotlight for bold moves like Lessen’s $950M acquisition of SMS Assist, one of the largest proptech deals in industry history. Today, with 30,000+ vendors and more than 4 million work orders processed annually, Lessen is transforming property services with AI innovations like Lessen Copilot and our Advantage Marketplace. It’s fast growth with real impact — and we’re just getting started....Show more

2. Our founder and CEO, Jay McKee, was recently selected by Commercial Observer for their Power Proptech list — a recognition reserved for leaders driving the future of real estate technology. Jay earned that spotlight for bold moves like Lessen’s $950M acquisition of SMS Assist, one of the largest proptech deals in industry history. Today, with 30,000+ vendors and more than 4 million work orders processed annually, Lessen is transforming property services with AI innovations like Lessen Copilot and our Advantage Marketplace. It’s fast growth with real impact — and we’re just getting started.

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Lessen

6mo

1. Built In recently featured Richard Gray, Enterprise Sales Director in Lessen’s Commercial division, in its spotlight on enterprise sales leaders. Richard shared how his 15 years across commercial real estate, facilities management, and tech-enabled services shaped his approach to enterprise partnerships: “Selling to enterprises takes empathy, data, and a deep understanding of the customer’s world. Each deal is like solving a puzzle, and the reward is seeing your solution improve performance across hundreds or thousands of locations.” At Lessen, that philosophy drives how our team helps large, multi-site operators modernize facilities management and deliver measurable impact. https://builtin.com/articles/what-its-work-these-enterprise-sales-team#Lessen...Show more

1. Built In recently featured Richard Gray, Enterprise Sales Director in Lessen’s Commercial division, in its spotlight on enterprise sales leaders. Richard shared how his 15 years across commercial real estate, facilities management, and tech-enabled services shaped his approach to enterprise partnerships: “Selling to enterprises takes empathy, data, and a deep understanding of the customer’s world. Each deal is like solving a puzzle, and the reward is seeing your solution improve performance across hundreds or thousands of locations.” At Lessen, that philosophy drives how our team helps large, multi-site operators modernize facilities management and deliver measurable impact. https://builtin.com/articles/what-its-work-these-enterprise-sales-team#Lessen

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Photos

Lessen photo of: Employee Appreciation Week 2024

Lessen awards and accolades

Gold Stevie Award - Contact Center of the Year (Up to 100 Seats) – Other Service Industries, The Stevie Awards, 2025
BuiltIn's 2024 Best Places to Work: Chicago, BuiltIn, 2024

Jobs at Lessen

Customer Escalations Representative IV

Customer Escalations Representative IV

Vendor Sourcing Specialist

Vendor Sourcing Specialist

Senior Software Developer I

Chicago, IL

·

US$109K - US$146K /yr

(Glassdoor Est.)

View job

Employee reviews at Lessen

Lessen has an employee rating of 2.2 out of 5 stars, based on 179 company reviews on Glassdoor which indicates that most employees have an average working experience there. The Lessen employee rating is 41% below average for employers within the Real estate industry (3.8 stars).

Ratings by category

3.0

Diversity and inclusion

2.8

Work/Life balance

2.6

Compensation and benefits

2.2

Culture and values

2.1

Career opportunities

1.9

Senior management

Employee reviews

Software qa engineerFormer employee

1.0

Potential for quality work hampered by ineffective leadership

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Lessen

Lessen Snapshot