Director, Programs Learning and Development

Compass Working Capital•Boston, MA

just now•$95,500 - $125,000•Hybrid

About The Position

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.

Requirements

Commitment to Compass' 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.

Nice To Haves

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.

Responsibilities

Design and lead Compass's comprehensive internal learning strategy for the Programs Department staff that advances organizational goals, supports national 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.
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.
Provide strategic direction, mentorship, and performance management to Manager of Programs Learning & Development and learning team, setting clear goals and ensuring 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
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 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.

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 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