Full-Time

Senior DevOps Engineer 1

Posted on 9/17/2025

Lessen

Lessen

1,001-5,000 employees

Property services marketplace and SaaS platform

Compensation Overview

$90k - $120k/yr

Chicago, IL, USA

In Person

Category
DevOps & Infrastructure (1)
Required Skills
PowerShell
Bash
Kubernetes
Microsoft Azure
Agile
Python
Java
AWS
Go
Jenkins
Terraform
SCRUM
DevOps
Linux/Unix
Requirements
  • Bachelor’s Degree in Computer Science, Computer Engineering or equivalent professional experience
  • 4+ years of prior experience in DevOps, Site Reliability or Platform Engineering
  • Highly proficient in one of programming languages such as Python, Go or Java
  • Strong Scripting Skills in Bash or PowerShell
  • Strong background in Public clouds like AWS or Azure along with infrastructure as a code(Terraform, CDK)
  • Strong Experience with continuous integration and related tools such as Jenkins Pipelines, GitHub Actions, ArgoCD, Gitlab CI, SonarQube
  • Experience in managing Kubernetes Clusters
  • Experience with Scrum and Agile workflow methodologies
Responsibilities
  • Recommend alternate choices and trade-offs for various design decisions; investigate performance and process failures and work to improve them.
  • Developing and build IT solutions, install and configure solutions, implement reusable components, translate technical requirements, and assist in all stages of the software development cycle.
  • Stay apprised of new developments in both Azure and AWS cloud operations and help in determining architectural solutions to enhance the stability and performance of the infrastructure.
  • Gain a deep application-level knowledge of the systems as well as contributing to their overall design.
  • Work closely with other internal teams to build security, reliability, and scalability into the development lifecycle.
  • Dive deep into the software stack to troubleshoot as needed and in resolving Windows and Linux operating system issues.
  • Be on call as a part of rotating support schedule and respond to production issues and incidents in a timely manner.
  • Build engineering automation and productivity tools to streamline and scale applications in the production environment.
  • Build from the ground up reliable infrastructure services in AWS and Azure to deliver highly scalable services.
  • Automate cloud operations using Infrastructure as Code tools and Configuration management tools.
  • Ensures the confidentiality of internal and external data
  • Performs ad-hoc projects and other duties as assigned
Desired Qualifications
  • Certified AWS Solutions Architect- Associate or higher
  • Azure Fundamentals or higher
  • Any Kubernetes Certifications (KCNA, KCSA, CKAD, CKA, CKS)
  • HashiCorp Certified: Terraform Associate

Lessen provides a technology-powered end-to-end platform that connects property owners with a network of verified professionals for maintenance, repairs, and renovations. Its marketplace plus SaaS tools manage bidding, scheduling, payment, and quality control across portfolios. Unlike general property marketplaces, Lessen targets institutional investors, property managers, and real estate owners, offering integrated procurement and portfolio management. Its goal is to simplify and scale property maintenance and renovations, delivering transparent, auditable workflows while generating revenue from transaction fees and software subscriptions.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$1.2B

Headquarters

Scottsdale, Arizona

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Aiden AI platform reshapes facilities management for residential and commercial real estate.
  • $170M Series B funding values Lessen over $1B, fueling expansion.
  • Acquisition of Blue Skyre IBE expands global facilities management capabilities.

What critics are saying

  • ServiceChannel's AI platform erodes Lessen's market share in 12-24 months.
  • Jobber captures multifamily clients, cutting Lessen's transaction fees by 20-30% in 6-12 months.
  • Yardi's proprietary module commoditizes Lessen's SaaS fees in 3-6 months.

What makes Lessen unique

  • Lessen integrates Lessen360 with Yardi Voyager for real-time work order synchronization.
  • Lessen Advantage Marketplace provides vendors 18% savings on products via One Source.
  • Lessen serves over 1 million properties with 30,000 vetted vendors nationwide.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

Paid Vacation

Parental Leave

Career Advancement Opportunities

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
France Media
Mar 5th, 2025
Lessen Opens New 76,932 SF Office in Downtown Chicago

Lessen opens new 76,932 SF office in downtown Chicago.

Business Wire
Jan 6th, 2025
Lessen Announces Integration with Yardi, Offering Seamless Access to On-Demand Services and Maintenance Solutions

Lessen360(TM), a cloud-based platform purpose-built for centralized maintenance operations, is now fully integrated with Yardi Voyager, enabling real-time synchronization of work orders and make-readies between the platforms.

Business Wire
Apr 2nd, 2024
Lessen Launches Innovative Purchasing Marketplace For Vendors

SCOTTSDALE, Ariz.--(BUSINESS WIRE)--Lessen, the premier tech-enabled, end-to-end solution for outsourced real estate property services, today announced the launch of the “Lessen Advantage Marketplace.” This centralized, dynamic hub allows vendors who are part of the Lessen Advantage™ community to enjoy access to a diverse range of products and services geared toward maximizing efficiency and fostering growth. The Marketplace includes access to preferred rates on insurance and bank financing, as well as access to thousands of products and materials through One Source, an integrated e-commerce purchasing hub. On average, users will benefit from savings of over 18% compared to prevailing retail prices. "We want to help our vendor community to save time and money on all of their projects,” said Lessen founder and CEO Jay McKee. "Our marketplace is another step forward in our goal to transform how property services are managed.”

Business Wire
Nov 30th, 2023
Real Estate Marketplace Platform Lessen Closes $170 Million Series B Funding Round

Lessen announces that it has closed a $170 million Series B funding round along with a company valuation of more than $1 billion.

The Business Journals
Sep 27th, 2023
First look: Scottsdale-based proptech firm expands into new amenity-filled headquarters

Scottsdale-based Lessen Inc. will stay within the city but has moved offices from 4021 N. 75th Street into the Portales Corporate Center I at 4800 N. Scottsdale Road.

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