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Sales Director

Lessen

ILJobPosted todayStill listed today

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At a glance

Compensation
No compensation found
Location
IL
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

The Sales Director is an individual contributor responsible for growing existing accounts and opening new business opportunities in key market segments, including retail, financial services, and healthcare. The role works with clients and the business development team to grow enterprise customers. It involves building facilities solutions, engaging executives, developing a sales pipeline, and partnering with customer success and account operations.

Skills & qualifications

RequiredNice to have

Skills

Sales, nice to haveAccount Management, nice to haveNew Business Development, nice to haveCustomer Relationship Management, nice to haveSales Enablement, nice to haveFacility Management, nice to haveEnterprise Sales, requiredQuota Attainment, nice to haveDirect Sales, nice to haveChannel Sales, nice to haveReferral Partner Sales, nice to haveEnthusiasm, nice to haveEmpathy, nice to haveCuriosity, nice to haveMotivation, nice to haveReliability, nice to have

Qualifications

Bachelor's Degree, nice to have5+ Years Enterprise Sales Experience, required

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
401(k) Match
Paid Time Off
Parental Leave

Full 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 Sales Director is an individual contributor role that is responsible for managing and growing existing account relationships and opening new business opportunities for Lessen in one or more of the company’s key market segments including retail, financial services, and healthcare. This individual will interface heavily with both clients and the business development team to grow Lessen’s enterprise customers.

What You'll Do:

  • Meet or exceed annual sales quota

  • Build integrated facilities solutions on the Lessen platform that meet customer goals and deliver industry-leading performance across complex real estate and national facilities footprints

  • Engage C-level executives and collaboratively build compelling business cases for Lessen’s services

  • Develop and maintain a sales pipeline consistent with territory growth goals

  • Develop thought-leadership in your target industry through engagement with trade organizations

  • Provide forecast predictability and accuracy

  • Support the development and effectiveness of inside sales resources

  • Partner with customer success and account operations to establish and grow new customer relationships

What You'll Need:

  • Bachelor’s degree preferred

  • 5 years of enterprise sales experience in facilities management, real estate equipment and services, technology or services required

  • Proven track record of exceeding quota in a direct sales role

  • Experience selling through channel or referral partners

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.

How this job compares

Set against the 1,383 open Sales Director jobs on Olive Jobs, counted November 10, 2026.

Pay
  • This postingNot listed
  • Illinois median$150–225K/yr48 salary ranges
  • US median$29–39/hr31 hourly ranges
Openings
Olive Jobs lists 65 open Sales Director jobs in Illinois and 1,383 across the US. 18% of them nationwide are listed as remote or flexible.
Hiring the most in Illinois
Experience
This posting asks for at least 5 years of experience; Sales Director postings that state a minimum ask for 7 years at the median (1,066 postings).
Education
360 of the 1,383 open Sales Director jobs (26%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on November 10, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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