We are looking for a strategic and operational leader responsible for overseeing the delivery of financial coaching and program implementation within Compass’s opt-out model outlined in Compass’ seven-year strategic plan.  

Skills We’re Looking For 

• Proven ability to coach, mentor, and hold teams accountable to performance standards while driving innovation. 

• Comfort with change, ambiguity, and testing new service delivery models. 

• Exceptional analytical, organizational, time management, and communication skills, with a focus on innovation and continuous improvement.  

• Proven ability to drive collaboration and influence across diverse teams and stakeholders.  

• Proactive problem-solver. Ability to navigate and trouble-shoot unexpected changes. Reliable.    

• Ability to prioritize competing priorities in ways that advance high quality outcomes. Ability to identify, anticipate, and mitigate risks, and to keep others on track.  

• Passion for data and dashboards. Experience working with data systems (e.g. Salesforce) and using data to drive decisions. 

About the Role 

This role combines direct supervision of a financial coaching team and operational leadership of our partnership with the Chicago Housing Authority (CHA) with cross-functional coordination across departments to ensure client success, service quality, and program fidelity. The position is based in Chicago, reflecting the importance of local presence and engagement in advancing our work in the region. 

 The opt-out model departs from Compass’s traditional portfolio-based approach to coaching, offering on-demand coaching designed to lower access barriers and serve a broader population at scale. This manager plays a key role in executing this strategy, driving outcomes, and fostering a high-performing, equity-driven team culture. 

This position reports to the Director of Programs and acts as the liaison between Compass and designated housing partners. 

Primary Responsibilities:  

Team Leadership & People Management 

• Supervise and support a team of coaches ensuring alignment with client engagement benchmarks and quality expectations. 

• Oversee hiring, onboarding, training, and performance management, with a focus on developing staff capacity in an on-demand coaching model. 

• Foster a culture of collaboration, accountability, and continuous improvement through regular coaching observation, feedback, and support. 

Program Operations & Partnership Management 

• Maintain oversight of critical workflows such as onboarding, coaching delivery, data entry, and escrow-related processes. 

• Coordinate hotline and app-based client support coverage, especially during peak outreach periods. 

• Ensure program manuals and resources are consistently updated to reflect current policies and best practices.  

• Act as a subject matter expert, fielding programmatic questions from outreach and coaching teams and leading cross-functional training to ensure alignment and understanding of program policies and procedures.  

• Liaise with external partners (e.g., CHA) fostering strong, collaborative relationships to coordinate program requirements, troubleshoot challenges, and support strategic learning goals. 

• Prepare and deliver high-quality dashboards, reports, and other key deliverables for partner organizations, providing insights that support decision-making and program success.  

Client Experience & Quality Assurance 

• Lead quality assurance reviews of coaching documentation, client interactions, and service outcomes. 

• Respond to client concerns and trends in service delivery with empathy and accountability. 

• Use data insights and client feedback to identify gaps, improve systems, and ensure culturally responsive, accessible service.  

• Collaborate across departments to develop creative solutions and streamline operations for optimal client outcomes and to establish best practices. 

• Support implementation of digital tools and app-based resources to increase accessibility and client engagement. 

Program Learning & Continuous Improvement 

• Monitor performance data to ensure program goals are met and coach performance remains consistent. 

• Contribute to innovation and refinement of the opt-out model by piloting new workflows and surfacing best practices, with a focus on employing a Lean Impact approach to problem solving including falling in love with the problem and not any single solution.  

• Support internal evaluation processes and contribute to reporting and storytelling about program impact. 

• Proven ability to coach, mentor, and hold teams accountable to performance standards while driving innovation. 

• Comfort with change, ambiguity, and testing new service delivery models. 

• Exceptional analytical, organizational, time management, and communication skills, with a focus on innovation and continuous improvement.  

• Proven ability to drive collaboration and influence across diverse teams and stakeholders.  

• Proactive problem-solver. Ability to navigate and trouble-shoot unexpected changes. Reliable.    

• Ability to prioritize competing priorities in ways that advance high quality outcomes. Ability to identify, anticipate, and mitigate risks, and to keep others on track. 

Qualifications and Competencies: 

Required 

• 4+ years of relevant work experience with at least 2 years of experience managing staff or leading teams 

• Commitment to Compass’s mission and values, with a passion for advancing financial mobility and equity for families with low incomes.  

• Cultural humility and respect for diverse cultures, identities, and lived experiences.  

• Trustworthy, with strong interpersonal skills, maturity, self-awareness, empathy, integrity, sound judgment, and ability to establish and build strong, trusting partnerships.  

• Excellent written and verbal communication skills, including ability to explain complex information in plain language.   

• Willingness to work one evening per week (until 7:30 pm) and one Saturday per month. 

• Ability to fulfill in-person job duties as needed for partner meetings, travel to on-site events to support outreach and engagement efforts, etc.  

Preferred  

• Experience in professional development, fostering team growth, and cultivating a positive team culture.  

• Background in project management or change management.  

• Previous experience in subsidized housing, asset-building, financial coaching and capability, economic mobility or antipoverty work, including the FSS program, is preferred.  

This position is tied to a three-year program partnership, with the potential to grow into other opportunities at Compass as the initiative evolves. 

Benefits   

• The salary range for this role is $85,000 - $96,500, commensurate with experience. We’ll promote your professional growth and development by providing access to a competitive salary and benefits package and additional employee benefits that include but are not limited to:  

• Healthcare: medical, dental, vision: Compass covers up to 80% of employee premiums and 80% for dependents. There is no waiting period to enroll in health insurance.  

• Retirement plan 401(k) & 3% match   

• Parental Leave: Employees who have been employed for at least three (3) months are eligible to take up to 12 weeks of unpaid leave. *Employee must be with the organization for six (6) months to receive up to six (6) weeks of full pay from the organization.  

• Life insurance & disability Insurance   

• Paid time off: Employees receive up to 36 Wellness days and 8 holidays per calendar year, plus the final week of the calendar year off as an organizational wide holiday. All employees enjoy a two-hour early closure starting the Friday after Memorial Day through the week of Labor Day.  

• Flexible Spending Account (FSA)  

• Dependent Care Flexible Spending Account  

• Professional development & certification  

• Pre-tax commuter benefits  

• Employee Assistance Program (EAP)  

• Office closed the final week of calendar year  

• Equipment: $200 one-time stipend for work from home expenses  

• Internet Reimbursement: Up to $40 per month for personal internet expenses  
   

Equal Opportunity Statement  

Compass Working Capital is an Equal Opportunity Employer. We consider applications for all positions, without regard to age, race, color, ethnicity, national origin, ancestry, creed, religion, gender, gender identity or expression, sexual orientation, citizenship, physical or mental disability, medical condition, genetic information, marital status, veteran status, military status, or any other characteristic protected by applicable law.  

Compass Working Capital is committed to ensuring individuals with disabilities receive the accommodations required for them to interview for a position on our team. Should you require accommodations, please contact hr@compassworkingcapital.org.  

Compass also provides hiring preference to Section 3 residents. Section 3 Residency is defined as a “low-income resident” of the area where the HUD-assisted project is located.  

For the purposes of Section 3, "low-income" is defined as 80% of the Area Median Income. To learn more information about Section 3 income eligibility, please refer to the Housing and Urban Development (HUD) Website.