Lead strategy and execution of customer solutioning to drive measurable ROI and operational improvements. Build and lead teams delivering solution design, value realization, and strategic initiatives while partnering cross-functionally to influence product and operations and support growth, retention, and long-term customer relationships.
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 Vice President, Customer Solutions & Business Impact is responsible for leading the strategy, execution, and evolution of Lessen's customer solutioning function, ensuring customers realize measurable value from our technology, services, and nationwide vendor network. This executive leader serves as the bridge between customer needs, operational excellence, product innovation, and business outcomes. The VP will oversee solution design, business consulting, value realization, and strategic customer initiatives. Working closely with Sales, Customer Success, Operations, Product, and Executive Leadership, this role will help customers transform their property operations while driving growth, retention, and long-term partnerships.
This role will be a hybrid position located in Chicago, IL or Scottsdale, AZ.
What You'll Do:
- Lead the strategy and execution of customer solutions that drive measurable business outcomes and operational improvements.
- Partner with customers and internal stakeholders to align Lessen's capabilities with customer goals and long-term success.
- Develop and implement frameworks to measure, communicate, and maximize customer value and ROI.
- Serve as a trusted advisor to executive stakeholders, helping customers optimize property operations at scale.
- Build, develop, and lead a high-performing team focused on customer solutions, value realization, and business impact.
- Collaborate across Sales, Customer Success, Operations, Product, and Finance to deliver exceptional customer experiences and outcomes.
- Translate customer feedback, industry trends, and business insights into recommendations that influence product and operational strategy.
- Support strategic growth initiatives by demonstrating the business value of Lessen's solutions.
- Establish scalable processes, tools, and metrics that drive efficiency, customer satisfaction, retention, and expansion.
- Champion continuous improvement and innovation to enhance customer outcomes and strengthen long-term partnerships.
You Should Have:
- Bachelor’s Degree required
- 10+ years of leadership experience in customer solutions, consulting, business transformation, operations, customer success, or related fields.
- 5+ years leading high-performing, customer-facing teams.
- Proven track record of driving measurable business outcomes and customer value.
- Strong executive presence with experience influencing and presenting to senior stakeholders.
- Experience leading cross-functional initiatives across revenue, operations, product, and customer organizations.
- Demonstrated ability to build scalable customer engagement programs and leverage data to drive strategic business decisions.
- Experience in PropTech, facilities management, field services, construction technology, or related industries.
- Background in consulting, operational transformation, customer strategy, or enterprise SaaS environments.
- Experience developing ROI methodologies, business cases, and executive-level value reporting.
- Written Communication – Advanced
- Verbal Communication & Executive Presence – Advanced
- Strategic Analysis – Advanced
- Negotiation & Influencing – Advanced
- Process Improvement & Operational Excellence – Advanced
- Problem Solving & Decision Making – Advanced
- Cross-Functional Leadership – Advanced
- Customer Relationship Management – Advanced
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.
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
Manage major commercial construction projects across markets, overseeing design, staffing, schedules, subcontractors, budgets, procurement, quality, safety, risk mitigation, client communication, contract administration, and reporting. Visit sites, coordinate mobilization, prepare project documents and change orders, foster client relationships, and resolve issues to ensure project profitability and compliance.
Top Skills:
MS Office
Cloud • Real Estate • Software • PropTech
Manage multi-step planned and unplanned projects—including capital construction, maintenance, disaster relief, and EHS—coordinate vendors and clients, monitor vendor performance, ensure quality control and reporting, resolve escalations, onboard vendors, and serve as a senior resource and role model for other coordinators.
Top Skills:
ExcelMicrosoft WordOne Project Management ToolOutlookPmwebPowerPoint
Cloud • Real Estate • Software • PropTech
The Account Representative manages day-to-day facilities services for major clients, ensuring client satisfaction, operational success, and effective resource allocation while addressing client needs and improving operations.
Top Skills:
ExcelMicrosoft WordOutlookPowerPoint
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
