Lessen

Strategic Accounts Team Lead

Lessen · Chicago, IL
Chicago, IL $56K–$62K Posted 2026-07-14
Salary
$56K–$62K
Type
Full-time
Experience
5+ yr

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.

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.

Ensure total client satisfaction for assigned portfolio by managing a team of Account Representatives in the performance of their assigned responsibilities, holding them accountable for managing complex operational projects for clients of high strategic importance to Lessen

Achieve the client’s and Lessen’s financial objectives by evaluating the urgency and efficacy of requested work, determining appropriate resolutions of issues, and controlling to release of work to vendors; exercise budgetary approval authority and holds team members accountable for managing the client’s budget within the assigned portfolio to the client’s financial benefit

Develop professional relationships with client’s operational and functional managers and communicate the costs and benefits associated with service performance to ensure the client’s funds are allocated efficiently to meet their needs

Guide team members in the development of professional relationships with clients and vendors through collaborative communication, effective action on feedback, and occasional site visits

Closely monitor the operational and financial performance of all assigned operational teams to identify the root causes of process, approach, and/or program deficiencies; recommend resolutions to increase the client’s operational and financial efficiency

Enable and motivate team to proactively develop and implement solutions to complex and challenging client requirements that fall outside of standard procedure and historical precedent

Proactively manage direct reports’ response to client escalations in order to achieve resolution as quickly as possible, while escalating the most complex and consequential issues to department leadership with actionable recommendations for solutions

Identify the need to become engaged in potential issues prior to client escalation and work with team members to resolve high-priority issues; correctly identify issues that require escalation to department leadership, and raises them alongside actionable recommendations for solutions

Facilitate the two-way flow of information between team members and department leadership by maintaining continuous effective communication, leading team meetings, and providing complete and accurate team reporting to department leadership

Assist in the development and implementation of analysis tools to help the operations department identify trends and implement best practices for both internal and client business processes

Assist department leadership in the development and implementation of data tools to measure, track, and set standards for team performance; adhere to these goals and standards

Use KPIs and other quantitative indicators to manage team’s workflow and hold team members accountable to performance standards

Supervise team members’ work product and performance for quality, accuracy, and adherence to Lessen policy

Supervise and coach reports in preparation and delivery routine and ad hoc communications and qualitative reports to the client that are impactful and of high professional standards

Develop team members’ professional knowledge and competencies to continuously improve their performance and prepare them to take on increasing responsibility

Review team members’ performance; provides informal in-stride counseling and formal feedback at prescribed intervals

Contributes to the positive financial performance of the department by contributing to high service throughput volume and effective management of vendor costs

Ensures confidentiality of internal and external data

Performs ad-hoc projects and other duties as assigned

Bachelor’s Degree

2-5 years of related, progressive work experience required

Prior people management experience a plus

Experience in call center or customer service management a plus

Experience in facilities management, maintenance management, or building engineering, maintenance trades, or related fields a plus

Proficient in basic people management processes

Proficient in leading a small team on a day to day basis, within a broader organization structure

Computer Skills: Proficiency in Microsoft Word, Excel, PowerPoint, Outlook required

Familiarity with Tableau or other data visualization packages a plus

Tableau
$60K — 10th pctl $230K — 90th pctl
This role’s midpoint $59K vs. market median $130K for Operations roles
-55%
below median
Based on 13,000+ Operations roles with disclosed salary ranges tracked on NewJob.
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