Enterprise Sales Director, Multifamily

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.

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 Multifamily vertical. 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 multifamily residential 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 Multifamily Residential 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 within the multifamily industry.

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.