Sales Director, Commercial (Chicago)

Lessen is a tech-enabled, end-to-end property service provider transforming the delivery and management of commercial and residential real estate services at scale. Our technology platform offers data-driven insights that unlock growth opportunities across the entire real estate ecosystemincluding investors, owners, managers, and service providers. With a network of over 30,000 vetted vendors serving more than 1 million properties and completing over 3.5 million work orders annually, Lessen is a venture-backed, privately held company with offices in Scottsdale and Chicago.

The Sales Director role is a key individual contributor position responsible for managing and expanding existing account relationships and developing new business opportunities within one or more of our target market segments (K-12, logistics, retail, grocery, financial services, convenience stores, and healthcare). The role involves significant interaction with clients and the business development team to drive growth.

What You'll Do:

• Achieve or surpass annual sales targets.
• Effectively introduce and position the Lessen value proposition across various levels of prospect organizations.
• Engage C-suite executives, procurement, and business owners to promote fully outsourced or hybrid solutions, generating revenue through organic growth and referrals.
• Generate prospecting activities that exceed monthly quotas for contacts and appointments.
• Maintain a robust, 4X rolling annual sales pipeline.
• Provide accurate sales forecasting.
• Contribute to the development of inside sales resources.
• Maintain and nurture existing customer relationships through face-to-face meetings, calls, and emails.
• Communicate with customers to understand their needs and offer suitable solutions.
• Demonstrate Lessen's solutions and value propositions, addressing customer questions and concerns.
• Identify opportunities to expand Lessen's service offerings within existing accounts.
• Maintain current relationships and seek to grow services within the existing customer base.
• Keep detailed, up-to-date customer and industry data; participate actively in industry groups and associations.
• Update all sales activities and initiatives in salesforce.com .
• Apply appropriate sales strategies at all pipeline stages, addressing any weaknesses.
• Operate in accordance with financial, legal, and ethical policies; drive revenue and profit growth; manage the Sales P&L.
• Participate in multiple projects simultaneously, ensuring process adherence, monitoring progress, mentoring leads, and guiding successful implementations.
• Domestic travel up to 50% required.
• Foster a positive team environment.
• Maintain confidentiality of internal and external data.
• Perform ad-hoc projects and other duties as assigned.

You Should Have:

• Bachelors degree required.
• Minimum of 5 years of sales experience, including at least 3 years of complex sales to executives in large organizations, preferably in technology or facility services.
• Strong business development skills and sales pipeline management, with effective use of CRM systems such as Salesforce.com .
• Basic understanding of sales processes, methodologies, and data.

Why Lessen:

Competitive compensation

Health, Dental, Vision, Life, Disability insurance options

401K retirement plan

Paid vacation, holidays, and floating days

Maternity/Paternity leave

Opportunities for career advancement

All necessary tools for success

Lessen values diversity and is committed to attracting, developing, and retaining talented individuals from all backgrounds. We seek enthusiastic, empathetic, curious, motivated, reliable teammates to help us foster an inclusive culture. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran or disabled status, or genetic information.