Sales Director, Commercial
Lessen
Sales & Business Development
Chicago, IL, USA
Posted on May 14, 2025
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 up new business opportunities for Lessen in one or more of the company’s key market segments (K-12, logistics, retail, grocery, financial services, convenience store, and healthcare). This individual will interface heavily with both clients and the business development team to grow the business.
What You'll Do:
- Meet or exceed annual sales quota.
- Excel at the introduction and positioning of the Lessen value proposition at various levels of prospect organizations.
- Compel the C-Suite, procurement, or business owners to prioritize a fully outsourced solution or “a la carte” solution that generates revenue from base business organic growth, as well as from referrals.
- Create prospecting activity that exceed monthly quota for activity and appointments.
- Develop and maintain a 4X rolling annual pipeline.
- Provide forecasting predictability and accuracy.
- Contribute to the development and effectiveness of inside sales resources.
- Maintain and foster existing customer relationships via face-to-face appointments, phone conversations, and emails.
- Potentially maintain ongoing communication with customers to understand their needs and provide solutions.
- Demonstrate solution and value proposition and deal with customer issues, questions, and uncertainties.
- Potentially identify and deliver on any opportunities to increase Lessen's suite of offerings to existing customers.
- Potentially maintain relationships with the current install base and looks to expand services in each account
- Maintain up-to-date, detailed customer knowledge and industry data; serves as an active member of groups and associations related to the industry and relevant customers.
- Update all sales activity, initiatives by category, customer and status in salesforce.com
- Use appropriate selling strategies and techniques to engage clients at all stages of the pipeline, and identifies and addresses any weaknesses in the strategy
- Operate within Financial, Legal, and Ethical Policies; responsible for driving the growth of revenue and profit originating from the Sales department; manages the Sales Profit and Loss statement
- Participate and influence multiple projects at a given time, ensuring adherence to process, monitor progress, mentor project leads, and direct implementations to successful conclusion
- Domestic travel required up to 50%.
- Foster a positive team environment.
- Ensure confidentiality of internal and external data.
- Perform ad-hoc projects and other duties as assigned.
You Should Have:
- Bachelor’s degree required
- At least 5 years of sales experience and a minimum of 3 years of complex sales to executives in large organizations, ideally in technology or facility services required
- Strong business development process and sales pipeline orientation, including effective use of CRM systems such as Salesforce.com
- Basic knowledge of sales process, methodology and data required
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.