Enterprise Sales Director, Commercial

| Chicago, IL, USA | Hybrid
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Lessen is one of the fastest growing companies in the real estate services industry. Our proprietary technology platform provides clients with portfolio dashboards, the ability to review and approve project estimates, check in on project progress in real time and pay vendors all in one place! But we aren’t just a tech company. We are also a property service delivery company offering renovations, turns and maintenance to residential and commercial clients. Lessen recently acquired SMS Assist, an industry-leading facilities maintenance technology and delivery company. The new combined national footprint will serve more than 250,000 properties, facilitate approximately 2.5 million repair and maintenance orders, and complete nearly 20,000 renovation and turn projects per year. Lessen has quickly evolved from exciting startup to valued partner, delivering scalable and turnkey property services to our clients.

We are looking for a highly motivated and experienced Senior Sales and Business Development Executive to join our team and help us grow our facility management business within the Commercial Division. The ideal candidate will have a proven track record of success in developing and closing new business, as well as a deep understanding of the commercial property, real estate, and facility management industry.

What You'll Do:

  • You will be interacting, influencing, and developing relationships with senior leaders and C-suite executives, to drive their facility and real estate transformation strategy.
  • Work inter-departmentally to develop and execute detailed account plans/strategies to secure new logo customers.
  • Maintain hyper focus on identifying pain-points and develop a business-orient point of view that compels action.
  • Continuously “connect the dots” within your account relationships to create executive alignments and develop broad relationships and engagement across targeted teams and leadership.
  • Dedication to consistent pipeline generation and development
  • Exceed quarterly and annual sales goals.
  • Follow up with all clients and prospects in a timely manner and communicate effectively through all phases through deal close, implementations and launch to ensure success.
  • Responsible for in implementing business development strategies and leading growth initiatives based on the strategic direction set by Division and Company Leadership.
  • Establish a presence within the commercial real estate and facility management community through participation in industry bodies and organizations. Demonstrate thought leadership that highlights individual and company skills and capabilities.
  • Develop a detailed understanding of Lessen capabilities, service offerings, and value proposition.
  • Disciplined data hygiene: consistent and timely documentation of sales details, pipeline and forecast in Salesforce.
  • Deliver a consultative customer experience by identifying pain or opportunity in an existing process and demonstrating partnership alignment that translates into a compelling business-oriented outcome and impact.
  • End-to-end complex deal management and execution that enables success for both internal and external teams.
  • Plan and lead exceptional presentations that result in a strong and clear understanding of how complex features and functionality drive a direct impact.
  • Develop a deep understanding of each account's unique business and provide alternative options to effectively structure account strategies to support new business wins.
  • Domestic travel required up to 25%.

You Should Have:

  • Bachelor’s degree required
  • At least 10 years of business development experience and a minimum of 5 years of complex sales to executives in large organizations, ideally in technology or service delivery.
  • At least 5 years of sales experience within the Commercial facility management industry.
  • Strong negotiation skills including contract language, legal requirements, and financial terms.
  • 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.
  • Experience closing complicated solutions to senior operational stakeholders.

Why Lessen:

· Competitive compensation

· 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. 

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130 E. Randolph Street, Chicago, IL 60601

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