Director, Programs Learning and Development

Company: Compass Working Capital
Location: Boston
Posted on: April 3, 2026

Job Description:

Director, Programs Learning and Development Boston | Full -Time | Partially - Remote About the Job The Director of Programs Learning & Development leads the strategy and execution of Compass's comprehensive internal learning, training, and knowledge management systems for Programs staff, primarily focused on financial coaching staff, outreach specialists, and program managers that interface with housing partners. This leader ensures that Programs staff receive timely, relevant, and trauma-informed training that aligns with Compass's values, strategic goals, and evolving client needs. The Director oversees development pathways, oversees the organization's financial content knowledge center, and ensures learning infrastructure supports Compass’s growth, advances equity goals, and strengthens both staff capability and client outcomes. This role requires strategic vision in adult learning and organizational development combined with hands-on leadership in curriculum design, content development, and training delivery. The Director provides strategic direction to the Manager of Programs Learning & Development and partners with senior leadership to align learning strategy with organizational priorities and field-building goals. Reporting structure: Reports to the Chief Programs Officer (CPO) Skills We Are Looking For: Expertise in adult learning with demonstrated ability to design learner-centered programs. Experience in curriculum strategy & development, including building scalable learning frameworks, competency models, and blended learning solutions aligned to organizational goals. Strong background in talent development, including leadership development, performance enablement, and employee growth strategies. Demonstrated success in cross-team leadership & influence, with the ability to partner effectively with executive leadership, HR, and business unit leaders to drive learning initiatives and organizational change. Strategic and entrepreneurial mindset, with the ability to identify gaps, innovate solutions, pilot new programs, and scale high-impact learning initiatives. Advanced project management skills, including the ability to manage multiple complex initiatives simultaneously, oversee budgets, establish metrics, and deliver results on time and within scope. Primary Responsibilities Programs Learning Strategy & Vision Design and lead Compass's comprehensive internal learning strategy for the Programs Department staff that advances organizational goals, supports national-level expansion, and strengthens program quality and client outcomes across all markets. Partner with senior leadership to identify emerging learning needs based on strategic priorities, market trends, program evolution, and operational requirements. Ensure learning strategy supports operational needs and program performance goals. Lead innovation in learning approaches, including exploration of new training modalities, technology platforms, and pedagogical methods. Establish metrics and evaluation frameworks to assess learning impact on staff performance and client outcomes. Curriculum & Knowledge Management Oversee development of comprehensive curriculum architecture and internal training programs, including onboarding, leadership development pathways, and specialized content tracks that support career progression across all Programs roles. Build and maintain a robust infrastructure and knowledge bank for providing high-quality, reliable financial coaching content with accuracy across geographies and program models; including on-demand financial content support to coaching teams across core topic areas including general best practices in financial capability, credit and debt management, and student loans, among others. Establish governance and knowledge management systems for internal and client-facing financial content, ensuring accuracy, accessibility, cultural responsiveness, and alignment with evolving financial mobility best practices. Oversee development of accessible, multilingual client-facing financial education resources, workshops, and newsletters that strengthen client knowledge, engagement, and outcomes. Set standards for trauma-informed, culturally responsive, and equity-centered learning design across all content. Team Leadership & Capacity Building Provide strategic direction, mentorship, and performance management to Manager of Programs Learning & Development and learning team, setting clear goals and ensuring the team has resources to achieve objectives. Build organizational capacity by developing train-the-trainer programs, cultivating subject matter experts, and creating systems that enable managers to effectively support staff development within their teams Lead evaluation and implementation of learning technology platforms that support virtual training, asynchronous learning, and performance support Cross-Functional Partnership & Systems Integration Collaborate with HR and senior leadership to integrate learning strategy with talent management, performance systems, and career development frameworks while advising on organizational learning needs, capability gaps, and opportunities for training investments. Create scalable systems that support learning delivery across geographically distributed teams, gathering and applying staff feedback, performance data, and quality assurance findings to improve learning outcomes. Champion a culture of learning across the organization through peer exchange, cross-collaboration, communities of practice, and shared innovation. Partner with Training & Technical Assistance team to align internal best practices with external training offerings and leverage field insights to inform internal learning strategy. Qualifications We seek a Director of Programs Learning & Development who is a strategic thinker and hands-on leader with deep expertise in adult learning, curriculum design, and organizational development. The ideal candidate will be a collaborative, equity-minded educator who values feedback, continuous improvement, and building systems that support both staff and client success. We are most likely to be interested in your candidacy if you can demonstrate most of the qualifications and experiences listed below: Commitment to Compass's mission and values, with a passion for advancing financial mobility and equity for families with low incomes. Commitment to culturally humble, trauma-informed learning practices that center equity and inclusion. 5-7 years of relevant experience in adult learning, training, or curriculum development with at least 3 years in leadership roles. Demonstrated experience leading learning and development functions, including strategy development, curriculum design, and training delivery. Strong background in adult learning principles, instructional design, and facilitation with proven ability to design engaging and effective training experiences. Experience managing staff and developing high-performing teams committed to learning and continuous improvement. Expertise in building and maintaining knowledge management systems and content repositories. Experience with learning management systems, data systems (such as Salesforce), and tools for tracking training participation and outcomes. Strong project management and organizational skills with ability to manage multiple workstreams, balance competing priorities, and meet deadlines. Excellent written and verbal communication skills, including the ability to translate complex content into accessible training and learning tools. Ability to establish and build strong, trusting relationships with colleagues across departments and functions in a remote, geographically dispersed environment. Preferred Familiarity and expertise in financial coaching, asset-building, or economic mobility strategies strongly preferred. Background in change management or organizational development. Experience scaling learning systems in a growing organization. This job description is not intended to provide a comprehensive listing of all duties or responsibilities. Job duties and responsibilities may change at any time based on organizational strategy and learning needs. Benefits The salary range for this role is $95,500 - $110,250, 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 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 off and Fridays in August 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 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@ comp as s workingcapital.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 .

Keywords: Compass Working Capital, Boston , Director, Programs Learning and Development, Human Resources , Boston, Massachusetts