The Director of Vendor Sourcing oversees vendor programs, drives operational excellence, and develops sourcing strategies, while also managing teams and collaborating with various departments to achieve goals.
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
- People Management Skills
- 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
- Role Specific Skills
- Excellent Microsoft product skills - high-level experience with Excel and Word required
- Experience/ability to setup/lead meetings or plan remote business events required
- Minimum Qualifications
- Bachelor’s degree or related experience
- 7 or more years business experience
- Other Relevant Qualifications
- 4 or more years’ experience in facilities, supply chain, or procurement preferred
- 4 or more years of management experience preferred
Compensation
- $125,000.00 - 145,000.00 annually
- Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.
#IND1
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.
Top Skills
Excel
Microsoft Word
Lessen LLC Chicago, Illinois, USA Office
Lessen LLC Chicago, IL Office
203 N. LaSalle St., Suite 2200, Chicago, IL, United States, 60601
Similar Jobs at Lessen LLC
Cloud • Real Estate • Software • PropTech
The Enterprise Sales Director drives facility management growth in the Multifamily vertical, develops relationships with executives, implements strategies, and exceeds sales goals. Responsible for business development, pipeline management, and complex deal execution, they ensure successful client interactions and strategic account management.
Top Skills:
Salesforce
Cloud • Real Estate • Software • PropTech
The Sales Enablement Analyst will support sales processes, assist with content creation, manage sales data, conduct account research, and help deliver presentations while ensuring high standards in client-facing materials.
Top Skills:
ExcelHubspotMicrosoft WordOutlookPowerPointSales NavigatorSalesforceSmartsheet
Cloud • Real Estate • Software • PropTech
The Senior Software Developer oversees a team, manages software development processes, implements methodologies, and mentors junior developers, while ensuring high-quality enterprise-grade software delivery.
Top Skills:
C#CSSHTML5JavaJavaScript
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

