1

Lessen Jobs in Illinois (NOW HIRING)

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 ...

Account Representative

Chicago, IL · On-site

$42K - $48K/yr

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 ...

Account Representative

Chicago, IL · On-site

$42K - $48K/yr

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 ...

Senior Software Developer I

Chicago, IL · On-site

$56.25 - $74.25/hr

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 ...

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 ...

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 ...

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 ...

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 ...

Jr. Associate Account Manager

Chicago, IL

$42K - $57K/yr

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 ...

Pharmacy Manager Local Specialty

Woodridge, IL · On-site

$64.50 - $75.75/hr

Maintains awareness of third-party pharmacy business opportunities and assures proper administration and implementation of third-party pharmacy systems and procedures to lessen payment rejections.

next page

Showing results 1-20

Lessen information

What are Lessen jobs?

Lessen is a property services company that connects property owners with local service professionals for property maintenance, repairs, and renovations. Jobs at Lessen typically involve roles such as project management, field operations, customer service, software development, and skilled trades like plumbing or electrical work. Employees at Lessen help streamline property upkeep for clients, ensuring quality service and timely project completion. Working at Lessen may also involve using technology platforms to coordinate tasks, schedule work, and communicate with clients and contractors.

What jobs pay 2000 a day?

High-paying jobs that can pay around $2,000 a day typically include specialized roles such as surgeons, anesthesiologists, corporate lawyers, or senior executives, often requiring advanced degrees, certifications, and significant experience. Freelance consultants, certain sales positions, and skilled trades like commercial pilots or project managers in large firms may also reach this level with the right client base or project scope.

What is the difference between Lessen vs Delivery Driver?

AspectLessenDelivery Driver
Required CredentialsBusiness or retail management experience, customer service skillsValid driver’s license, vehicle insurance, sometimes a commercial driver’s license
Work EnvironmentOffice, retail stores, or warehouse settingsOn the road, making deliveries, working outdoors or in vehicles
Employer & Industry UsageRetail, logistics, or delivery service companiesCourier, food delivery, logistics companies

While Lessen focuses on managing retail or business operations, Delivery Drivers primarily handle transportation and delivery tasks. Both roles require customer interaction but differ in work environment and credentials. Understanding these differences helps job seekers find the right fit based on skills and career goals.

What are the key skills and qualifications needed to thrive as a Property Maintenance Coordinator, and why are they important?

To thrive as a Property Maintenance Coordinator, you need strong organizational skills, knowledge of property management procedures, and experience in coordinating repairs or maintenance, often supported by a background in facilities management or real estate. Familiarity with property management software, work order systems, and budgeting tools is typically required. Excellent communication, problem-solving, and customer service skills help you effectively liaise between property owners, tenants, and service providers. These skills are crucial for ensuring timely maintenance, tenant satisfaction, and efficient property operations.

What are some common challenges faced by professionals working in property management roles at Lessen, and how can they be addressed?

Professionals in property management roles at Lessen often navigate the complexities of coordinating maintenance, managing vendor relationships, and ensuring resident satisfaction across multiple properties. Meeting tight deadlines, handling emergency repairs, and balancing client expectations can be challenging yet rewarding aspects of the job. Success typically involves strong communication skills, efficient use of Lessen’s technology platform, and proactive problem-solving. Collaborating closely with both internal teams and external service providers helps streamline processes and deliver consistent results.

Which jobs are shrinking?

Jobs in manufacturing, retail, and administrative support have experienced declines due to automation, technological advancements, and shifting market demands. Roles requiring routine tasks are particularly vulnerable, while jobs emphasizing technical skills or adaptability tend to grow.

What jobs in the US pay 300,000 a year?

In the US, high-paying roles such as senior physicians, specialized surgeons, corporate executives, and certain investment bankers can earn $300,000 or more annually. These positions typically require advanced education, extensive experience, and often involve leadership or specialized skills in their respective fields.

What job makes $10,000 a month without a degree?

High-paying sales roles such as real estate agents, software sales, or financial advisors can earn $10,000 or more monthly without a degree, often relying on strong communication skills, experience, and commissions. Additionally, skilled trades like commercial plumbing or electrical work may reach this income level with experience and certifications, especially in high-demand markets.
What cities in Illinois are hiring for Lessen jobs? Cities in Illinois with the most Lessen job openings:
Infographic showing various Lessen job openings in Illinois as of June 2026, with employment types broken down into 1% As Needed, 84% Full Time, 14% Part Time, and 1% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution.
VP, Customer Solutions & Business Impact

VP, Customer Solutions & Business Impact

Lessen

Chicago, IL • On-site

$170K - $225K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 20 days ago


Lessen rating

8.0

Company rating: 8.0 out of 10

Based on 6 frontline employees who took The Breakroom Quiz


Job 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 Vice President, Customer Solutions & Business Impact is responsible for leading the strategy, execution, and evolution of Lessen's customer solutioning function, ensuring customers realize measurable value from our technology, services, and nationwide vendor network. This executive leader serves as the bridge between customer needs, operational excellence, product innovation, and business outcomes. The VP will oversee solution design, business consulting, value realization, and strategic customer initiatives. Working closely with Sales, Customer Success, Operations, Product, and Executive Leadership, this role will help customers transform their property operations while driving growth, retention, and long-term partnerships.
This role will be a hybrid position located in Chicago, IL or Scottsdale, AZ.
What You'll Do:
  • Lead the strategy and execution of customer solutions that drive measurable business outcomes and operational improvements.
  • Partner with customers and internal stakeholders to align Lessen's capabilities with customer goals and long-term success.
  • Develop and implement frameworks to measure, communicate, and maximize customer value and ROI.
  • Serve as a trusted advisor to executive stakeholders, helping customers optimize property operations at scale.
  • Build, develop, and lead a high-performing team focused on customer solutions, value realization, and business impact.
  • Collaborate across Sales, Customer Success, Operations, Product, and Finance to deliver exceptional customer experiences and outcomes.
  • Translate customer feedback, industry trends, and business insights into recommendations that influence product and operational strategy.
  • Support strategic growth initiatives by demonstrating the business value of Lessen's solutions.
  • Establish scalable processes, tools, and metrics that drive efficiency, customer satisfaction, retention, and expansion.
  • Champion continuous improvement and innovation to enhance customer outcomes and strengthen long-term partnerships.

You Should Have:
  • Bachelor's Degree required
  • 10+ years of leadership experience in customer solutions, consulting, business transformation, operations, customer success, or related fields.
  • 5+ years leading high-performing, customer-facing teams.
  • Proven track record of driving measurable business outcomes and customer value.
  • Strong executive presence with experience influencing and presenting to senior stakeholders.
  • Experience leading cross-functional initiatives across revenue, operations, product, and customer organizations.
  • Demonstrated ability to build scalable customer engagement programs and leverage data to drive strategic business decisions.
  • Experience in PropTech, facilities management, field services, construction technology, or related industries.
  • Background in consulting, operational transformation, customer strategy, or enterprise SaaS environments.
  • Experience developing ROI methodologies, business cases, and executive-level value reporting.
  • Written Communication - Advanced
  • Verbal Communication & Executive Presence - Advanced
  • Strategic Analysis - Advanced
  • Negotiation & Influencing - Advanced
  • Process Improvement & Operational Excellence - Advanced
  • Problem Solving & Decision Making - Advanced
  • Cross-Functional Leadership - Advanced
  • Customer Relationship Management - Advanced

$170,000 - $225,000 a year
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.
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.