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.
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.
Lessen LLC Chicago, Illinois, USA Office
Lessen LLC Chicago, IL Office
203 N. LaSalle St., Suite 2200, Chicago, IL, United States, 60601
Similar Jobs at Lessen LLC
Cloud • Real Estate • Software • PropTech
Leads client discovery and analysis for facilities management solutions, analyzing operational and financial data, building business cases, developing proposals, and presenting executive recommendations. Partners with sales, operations, product, and implementation teams to shape deliverable solutions, support deal strategy, and create repeatable value models and enablement tools. Requires commercial facilities management expertise, financial modeling, advanced Excel, executive presentation skills, and experience with dispersed multisite portfolios.
Top Skills:
Excel
Cloud • Real Estate • Software • PropTech
Leads facilities operations for assigned commercial service districts, overseeing Facility Managers, CSRs, vendors, work orders, budgets, compliance, and client performance. Develops facilities strategies, monitors operational and financial KPIs, manages risks, improves processes, integrates technology, resolves escalated issues, develops vendor relationships, and mentors staff. Requires extensive facilities management experience, people leadership, vendor coordination, and strong communication and organizational skills.
Top Skills:
Automation ToolsProprietary Database
Cloud • Real Estate • Software • PropTech
Manages regional client and vendor relationships while supporting profitable business results through KPI tracking, vendor performance analysis, strategic sourcing, negotiations, and cost optimization. Conducts client needs assessments, aligns vendors geographically, supports quality control checks, assists estimation and project teams, resolves issues, and collaborates cross-functionally. Travel is expected up to 40% of the time.
Top Skills:
ExcelMicrosoft PowerpointMicrosoft WordReno WalkScopesy
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
