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Director of Evaluation & Learning

Job Details

Full Time
$100,084.00 - $100,084.00 Salary/year


Position Title: Director of Evaluation & Learning

Reports To: Chief Strategy Officer (CSO)

Community: Org-Wide

Office Location: Fully Remote (must be based in CA) 

Compensation: $100,084/annually, generous benefits package

Status: Full-time, exempt


About Fresh Lifelines for Youth

Fresh Lifelines for Youth is an award-winning non-profit whose mission is to partner with youth to unlock their potential, disrupt the pipeline to prison, and advance justice in California and beyond. By 2030, through partnering with young people, communities, and systems, FLY will contribute to the fight for equity and justice by taking concrete steps to dismantle California’s pipeline to prison, equip 30,000 youth to transform their lives and create meaningful opportunities for them to live healthy, free, and productive lives.


For more information about Fresh Lifelines for Youth, please visit:


Director of Evaluation & Learning - Position Summary

The Director of Evaluation and Learning is a strategic, innovative, collaborative, and results-oriented leader with strong research and evaluation skills applicable to informing programmatic and systems change impact, quality assurance, and organizational learning in a non-profit setting. They serve on the senior leadership team and collaborate closely with executive and senior leaders to advance organizational learning agendas, conduct program and systems change evaluations, and articulate the organization’s impact. They oversee the Evaluation and Learning Department to ensure it is responsive to organizational evaluation and learning needs while building and maintaining a data-informed culture. 


Specifically, the Director of Evaluation and Learning is responsible for leading FLY’s efforts and progress on its strategic evidence-building agenda, which at its core purpose aims to develop clear metrics, processes, and practices that help FLY learn and adapt in real-time so that we can respond to needs emerging through direct service and systems change efforts. The Director of Evaluation and Learning provides strategic thought leadership and evidence-informed guidance to both internal and external leaders, including identifying and working with key external partners (e.g., academic institutions, public agencies, and consultants). Success in this role will require consistent cross-organizational collaboration and making recommendations that can inform organizational learning to advance FLY’s strategic plan. 


Position Responsibilities

  • Advancing Organizational Learning

    • Oversee implementation and timely progress on FLY’s Learning Agenda and Strategic Evidence-Building Objectives.

    • Collaborate with the CSO and programs leadership to ensure strategic alignment of FLY’s programmatic and systems change efforts across multiple jurisdictions.

    • Manage key external partnerships to increase organizational capacity to evaluate impact and advance Learning Agenda.

    • Support CSO in managing FLY’s Board’s Learning and Impact Committee and the full Board’s understanding of FLY’s impact and learning objectives. 

    • Translate crucial evaluation findings into recommendations that, in collaboration with agency leaders, will inform and support the refinement of programs and systems change efforts in addition to informing key resource allocation and investment decisions. 

    • Lead the facilitation of FLY’s Theory of Change implementation meetings, set agendas, and strategically implement change within programs to achieve goals and outcomes.

    • Promote a data-driven culture of learning and accountability through the creation of systems for visualizing and using data to facilitate feedback loops with staff to support the improvement of program practices and organizational learning priorities.

    • Collaborate with non-program departments (e.g., Talent, Finance, Communication, etc.) to advance organizational learning across other functions.


  • Managing Department Operations

    • Serve as the leader for and manage the operations of the Evaluation and Learning Department 

    • Supervise the Evaluation and Learning Managers and oversee all personnel (including interns) to ensure individuals and the department, as a whole, advances toward its annual deliverables

    • Lead the design, utilization, and maintenance of FLY’s internal tracking system, Efforts to Outcomes (ETO), which supports the data and information needs of all FLY programs, the Board of Directors, funders, partnering agencies, and the entire FLY organization 

    • Assess FLY’s data system needs, make recommendations for changes or enhancements, and works with vendors to ensure FLY’s data system needs are successfully met.

    • Oversee the implementation of new projects as it relates to outcome and performance management, data collection methods, and reporting

  • Monitoring Organizational Performance

    • Generate weekly, monthly, and quarterly performance management reports for all program staff, managers, and agency directors to ensure programmatic health and grant execution

    • Generate and present quarterly organizational dashboards to the Board of Directors and senior leadership staff

    • Partner with Systems Change staff to continue to build out evaluation frameworks and tracking methods to understand and illustrate FLY’s impact

    • Design custom queries, Excel reports, and analysis tools to meet all program/systems change management and grant reporting needs

    • Work in partnership with Program Leadership to drive accountability and align FLY’s vision and Theory of Change with staff and program performance

    • Oversee the alignment of ETO usage and data collection methods with Theory of Change strategies, key indicators of success, and agency outcomes.

    • Collaborate with Development and Program/Systems Change Leadership to ensure the strategic alignment of potential grant applications/funding opportunities with FLY’s current practices and expected impact by providing outcome data and strategic recommendations as needed

    • Collaborate with the Director of Talent on annual staff performance reviews to ensure compliance on data-specific indicators as well as programmatic and individual deliverables.


Compensation & Benefits

This position is a full-time exempt role at a rate of $100, 084/annually with differential pay options based on an advanced degree and, when applicable to the role, speaking another language. Our Total Rewards Package also includes the following: 

  • Use a FLY-provided stipend towards various healthcare insurance options, dental, vision, retirement, life insurance policy, FSA (flexible spending account), dependent care, and more!

  • 10+ PTO Days

  • 12 Holiday Days

  • FLY provides 3-4 additional "rejuvenation days off" twice per year in July and December 

  • Wellness Funds ($300/year)

  • Professional Development Assistance ($175/year)

  • Acupuncture and Chiropractic Care. 

  • Employee Assistance Program (paid for by FLY)

  • Yearly Staff Retreat, Team “Dayaways,” Summer BBQ, and other FLY Events. 

  • Customize your Work Schedule (dependent on supervisor approval based on positional and departmental needs)

  • Hybrid of In-Office and Remote Work (frequency of required in-person work is dependent upon the role)

  • Opportunity for Employee Referral Bonuses

  • 8 Hours of Civic Engagement Hours

  • Mileage Reimbursement. 


At FLY, we have adopted a no-negotiation policy. This policy reflects our commitment to equity and ensuring that the offers we make to our candidates reflect competitive and appropriate compensation given the market and the role.


Our Commitment to Diversity, Equity, And Inclusion

At FLY, we embrace a diversity of identities, beliefs, thoughts, and experiences. We commit to creating an organizational culture of equity and inclusion to serve our youth and communities better. FLY is an Equal Opportunity Employer. We strive for an inclusive culture and a staff team that reflects diversity. Applicants for all job openings will be considered without regard to age, race, color, religion, sex/gender, national origin, sexual orientation, disability, veteran status or any other consideration made unlawful under any federal, state or local laws. We strongly encourage women; people of color, people who identify as part of the lesbian, gay, bisexual, transgender, and queer communities; people with experience in the juvenile justice or criminal justice systems; and people with disabilities to apply.  Fresh Lifelines for Youth is committed to offering reasonable accommodations to job applicants with disabilities. If you need assistance or accommodation due to a disability, please contact us at (408) 263-2630 or


COVID-19 Vaccination

At FLY, we are committed to the safety of our employees, clients, and all others who enter our workplace. As such, FLY would like to make clear that the COVID-19 vaccination is a condition of employment. However, FLY does allow staff to apply for exemptions based on medical history or sincerely held religious beliefs or practices. This must be approved through FLY’s compliance department. If you have any questions or would like to learn more, please contact us at (408) 263-2630 or email


What to expect

  • Application with 8-10 questions and an applicant screening question. 

    • No Cover Letter Required

  • 3 Interviews (for many roles, at least 1 would be in person)

  • Meet w/FLY youth

  • Work Product (Done in advance of the Final Round Interview)


Position Requirements

The ideal candidate will have a deep commitment to equity, social, racial, and economic justice. They will have expertise in quantitative and/or qualitative methods and evaluation design, past experience with the collection, reporting, and use of data for continuous improvement and a strategic mindset. The candidate will believe in FLY’s vision and mission and will resonate with FLY’s values: accountable, dedicated, respectful, equitable and just, loving, innovative, hopeful, and youth-centered. 


Core Competencies: Skills and behaviors that FLY expects and develops all staff to exhibit across all positions at various levels of proficiency (early stage, intermediate  and advanced) 

  • Cultural Competency: Demonstrates the values articulated by FLY’s Diversity, Equity and Inclusion definitions. Valuing diverse identities within the organization  and being self-aware of one’s own bias, power and privilege in different  relationships and settings 

  • Integrity: FLY defines integrity as owning your work, being accountable, and taking the initiative to produce excellent results. This also includes the customer service we show to our youth, their families, our colleagues, and stakeholders, as well as the ability to follow FLY policies and procedures. 

  • Collaboration: Ability to work productively within a team, contribute to the work with the big picture in mind (FLY’s mission and agency goals), and be mindful of exercising your strengths while also encouraging others to do the same. 

  • Communication: Uses effective written and verbal communication with staff,  teams, and communities served; demonstrates empathy, self-awareness, and listening skills.

  • Critical Thinking: Consistently identifies, gathers, and applies relevant information to complete work efficiently and effectively. 

  • Resiliency: Demonstrates the ability to adjust to change and work through ambiguity with growth and solutions-oriented mindset. This means openness to change and new perspectives and seeing change-related challenges as fluid and possible to overcome rather than fixed. 


FLY’s Leadership Competencies: Skills and behaviors that FLY expects and develops all staff in Leadership positions to exhibit across various levels of proficiency (early stage, intermediate  and advanced) 


  • Cultural Responsivity: Demonstrates the values articulated by FLY’s Diversity, Equity and Inclusion definitions. Valuing diverse identities within the organization and being self-aware of one’s own bias, power and privilege in different relationships and settings

  • Emotional Intelligence: Demonstrates self-awareness and ability to manage one’s own emotions, as well as the ability to recognize the emotions of others and respond with empathy. This includes maintaining a balanced and authentic perspective of issues and information daily.

  • Change Management: Ability to prepare effectively and guide teams through change and transition as needed. Able to assess the need and readiness for change and understand change-related dynamics.

  • Strategic Decision-Making: Effectively structures and facilitates strategic decision-making processes; responsibly makes informed decisions to improve organizational health and impact using key data, strategy, and problem-solving. 

  • Develops & Motivates Others: Motivates inspires and supports teams through strong coaching and mentorship. Builds healthy and effective teams through regular feedback, collaboration, setting clear expectations, and targeted development activities.

  • External Relationship Builder: Invests in and builds strong, trusted and ongoing relationships with external partners. Able to take the initiative to cultivate new relationships and assess and negotiate needed changes to existing partnerships.

  • Project Management: Able to create and implement increasingly complex project plans, manage those plans to their intended impact and adjust course as needed. This includes managing at various levels of complexity and scale, as well as anticipating potential barriers and executing to achieve excellent results. 


Note on Qualifications: In FLY’s quest for an equitable hiring process, candidates are encouraged to apply even if they feel they only meet 75% of the required job-specific qualifications.