Sales Director

Posted 11 Minutes Ago
Be an Early Applicant
2 Locations
Remote or Hybrid
Senior level
Cloud • Real Estate • Software • PropTech
Help us revolutionize real estate services.
The Role
Individual contributor responsible for expanding enterprise sales by managing existing accounts, generating new business, building facilities solutions, engaging C-level executives, maintaining pipeline and forecast accuracy, and exceeding quota. The role targets retail, financial services, and healthcare segments, requiring collaboration with business development, customer success, account operations, and channel partners.
Summary Generated by Built In
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. 

Skills Required

  • Bachelor's degree
  • More than 5 years of enterprise sales experience in facilities management, real estate equipment and services, technology, or services
  • Proven track record of exceeding quota in a direct sales role
  • Experience selling through channel or referral partners

What the Team is Saying

Jay Payne
Kirby Pumper
Maya Shea
Jay McKee
Jennifer Gordon
Trevon

Lessen LLC Compensation & Benefits Highlights

  • Healthcare Strength — Health coverage is described as comprehensive, including medical, dental, vision, mental‑health support, and supplemental options like FSAs/HSAs and pet insurance. Feedback suggests plan quality can be a relative bright spot, with some reports of favorable employee‑only costs in recent years.
  • Retirement Support — A 401(k) plan with employer matching is consistently highlighted in company materials and employee accounts. Feedback suggests the match (often cited as 50% up to a 4% employer contribution) makes retirement benefits a meaningful component of total rewards.
  • Leave & Time Off Breadth — Paid parental leave, flexible or unlimited PTO for some roles, holidays, sick time, and paid volunteer days are part of the offering. Feedback suggests the breadth of time off appears strong on paper, though experiences can vary by position.

Lessen LLC Insights

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The Company
HQ: Scottsdale, Arizona
713 Employees
Year Founded: 1999

What We Do

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. To learn more, visit Lessen.com.

Why Work With Us

We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.

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Lessen LLC Teams

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Commercial
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Lessen Direct - A Mobile Technician Workforce
About our Teams

Lessen LLC Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.

Typical time on-site: 3 days a week
HQScottsdale, AZ
Chicago, IL
Learn more

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