Managing Director of Programs

Compass Working Capital•Boston, MA

15m•$120,000 - $145,000•Hybrid

About The Position

The Managing Director of Programs (MDP) is a senior leadership role that oversees Compass’ direct service partnerships and coaching programs that bridges the gap between enterprise-level strategy, set by the Chief Program Officer, and functional execution, led by the Directors of Programs. The MDP provides the senior capacity to manage the complexity of high-impact, client-centered and culturally proficient program delivery, ensuring that growth does not outpace operational excellence. The MDP plays a critical role in the implementation of Compass’ strategic plan, testing an opt-out model for FSS and increasing our reach in new geographies. The MDP provides effective and inspiring leadership to the largest team in the organization and carries significant decision-making authority within the Programs Department, translating organizational priorities into actionable operational plans. This role oversees the entire direct service team including program management and coaching to ensure client-centered and culturally proficient service delivery

Requirements

Deep commitment to Compass's mission to end asset poverty for families with low incomes and close racial and gender wealth divides.
Exceptional capacity for managing and developing diverse teams of senior professionals, with focus on accountability, professional growth, and positioning staff to succeed.
10+ years managing high-quality, data-driven programs with proven success as a "leader of leaders" and track record of delivering outstanding results.
Candidates should have knowledge of affordable housing, community development, financial capability and/or asset building.
Demonstrated ability to lead teams through organizational transitions, rapid expansion, and implementation of new program models in fast-paced, entrepreneurial environments.
Ability to operationalize strategy by connecting program execution to broader organizational priorities and translating goals into actionable plans.
High proficiency in leveraging Salesforce/CRM systems and data dashboards to evaluate program quality, synthesize insights, and drive improvements.
Outstanding written and verbal communication skills, including ability to explain complex programmatic information in plain language to diverse audiences.
Capacity to lean-test new program designs, pivot quickly, navigate unexpected changes, and manage multiple priorities with strong organizational skills and attention to detail.
Proven ability to establish and maintain strong, trusting relationships with partners, demonstrating cultural humility and respect for diverse identities and lived experiences

Nice To Haves

Experience with operating or managing resident or supportive services in state or federal subsidized housing or programs supporting families with low incomes and/or prior experience with HUD’s Family Self-Sufficiency Program is a plus.
Background in behavioral science or human centered design preferred.

Responsibilities

Lead and oversee Compass's direct service FSS program portfolio, including program planning, performance, staffing, reporting, and compliance across all current and future programs.
Maintain deep expertise in FSS regulations and ensure program fidelity, including understanding HUD rules, funding notices, forthcoming changes, and ensuring all programs meet regulatory, contractual, and internal standards.
Manage direct service partnerships and contracts, cultivating relationships with decision-makers at partner organizations and overseeing contract work, pricing/revenue strategy, and delivery of contractual obligations.
Translate organizational strategy into operational execution, converting enterprise-wide strategic goals into domain-specific operational plans for direct service coaching and program functions.
Drive scale and transformation initiatives, leading the programs team through expansion periods and implementing new models (such as opt-out FSS) while maintaining alignment with Compass's mission and values.
Partner cross-functionally to optimize program performance, collaborating with Managing Directors of Impact & Innovation and Managing Director of Program Operations (MDPO) to monitor and improve program impact and operations using systems and dashboards.
Lead and mentor a high-performing team of Directors of Programs, focusing on their professional growth, accountability, and leadership development.
Partner with HR to strengthen talent development and succession throughout the department.
Articulate and be accountable for the department’s performance against Key Performance Indicators (KPIs) across teams to ensure strategic plan targets are met. Report performance against KPIs on a regular basis and strategize and implement pivots required to address any underperformance against targets.
Ensure consistent and high-quality client experience across all program types and partnerships, including development and implementation of financial coaching tools.
Strengthen a diverse, inclusive, and high-performing organizational culture within the programs department that is both trauma-informed and responsive.
Work in lockstep with the MDPO to ensure that service delivery across all programs is supported by robust infrastructure, compliance, and quality assurance systems.
Drive initiatives that require deep integration across departments (e.g., Marketing, HR, and Innovation), resolving bottlenecks, strengthening cross-departmental collaboration and driving innovative practices to achieve goals.
Leverage data insights from dashboards and CRM systems (Salesforce) to identify trends, refine service delivery, and implement actionable improvements.
Lead implementation of opt-out FSS program model with mission-aligned housing partners, incorporating lean testing, innovation, and learning agendas to build toward a national demonstration project.
Identify, develop, and champion innovative asset-building models within and beyond subsidized housing, collaborating with the CPO to cultivate and onboard new mission-aligned partners.
Serve as a strategic thought partner to the CPO and CEO on programmatic advancements, asset-building pathways, and sector-wide innovations.

Benefits

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 twelve (12) 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, and Fridays in August off as organizational wide holidays. 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)
Equipment: $200 one-time stipend for work from home expenses
Internet Reimbursement: Up to $40 per month for personal internet expenses