Director of Vendor Sourcing
Lessen
Chicago, IL, USA
Posted on Jan 20, 2026
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 Director of Vendor Sourcing directs and oversees all vendor programs for the department. This position is responsible for driving profitable business results and operational excellence by contributing to strategic planning and process improvement for our vendors.
Responsibilities
- Oversee a team/teams of Vendor Sourcing Specialists
- Monitor activities against department objectives and submit performance reports to senior leadership; address issues with urgency and correct areas of improvement
- Design, execute, and report on sourcing pipeline, including the ability to capture and convey insights in the data
- Develop and implement pricing negotiation and service term strategies
- Interact cross-functionally with all other departments and serve as an effective and value-added service for the entire organization
- Collaborate with other departments and leadership such as Operations and Affiliate Management to ensure sourcing strategies remain relevant, organizational goals are being met and delivery is on track, achieving customer goals and expectations
- Implement resolutions from other leaders and the team in analyzing opportunities and risks with vendors and the vendor onboarding team; recommend resolutions to leadership
- Accountable for the resolution of complex issues escalated by the client independently and with a sense of urgency; responsible for communication and resolution of issues
- Escalate the most consequential issues to executive leadership with actionable recommendations for solutions
- Develop and communicate a procurement business plan; establish, communicate, and implement long-term goals for the department in order to promote effectiveness and efficiency
- Develop, communicate and administer procurement team performance and development plans and appraisals
- Serve as the primary contact for procurement-related questions, training, policy, and procedure interpretation and alignment by all departments
- Develop and implement procurement-related training programs for the procurement team
- Develop a centralized procurement program that adds value and efficiency to the organization
- Develop and implement a targeted RFQ/RFP process to drive improved performance and increase profitability
- Serve as a liaison to operations leadership
- Ensure confidentiality and accuracy of internal and external data
- Responsible for executing full authority for personnel decisions; participate in departmental budgeting, strategic planning and procedural change
- Perform ad-hoc projects and other duties as assigned
- Must be available to adjust work schedule during high peak periods when necessary
- Travel, as needed, to meet vendors and assess and identify opportunities of growth or improvement of processes (potential travel of 10%)
Requirements
- Advanced proficiency in all people management processes, including recruitment, performance management and reward
- Advanced proficiency in building, growing and developing a team; including department structure design and resourcing
- Advanced proficiency in coaching and developing individual team members to reach their potential
- Proficient in engaging multiple teams through communication, processes, personal impact and influence
- Excellent Microsoft product skills - high-level experience with Excel and Word required
- Experience/ability to setup/lead meetings or plan remote business events required
- Bachelor’s degree or related experience
- 7 or more years business experience
- 4 or more years’ experience in facilities, supply chain, or procurement preferred
- 4 or more years of management experience preferred
People Management Skills
Role Specific Skills
Minimum Qualifications
Other Relevant Qualifications
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.