Director, Evaluation and Learning

Website Digital NEST, Inc.

Position Type: 100% FTE, Exempt

Compensation Range: $85,000 – 100,000 Annual Salary

Benefits Overview: Medical, Dental Vision & Life Insurance, Vacation & Sick Time Off, Paid Federal Holidays, Retirement plan

Organization Size: 50+ employees

Reports To: President and Chief Operating Officer

Location: Monterey Bay Area or North Central Valley, eligible for a Hybrid work schedule*

*After the first 90 days of employment, this position is eligible for a Hybrid work schedule. Candidates further than 40 miles from the Center location may be eligible for a hybrid work schedule earlier than the probationary period with hiring manager approval.



Digital NEST is a workforce development center that has welcomed thousands of youth from working-class, farmworker communities to develop the technical and professional skills they need to achieve their dreams. It is an exciting time for the NEST. We are focused on growth and expansion to five communities across The Monterey Bay and San Joaquin Valley Regions in Northern California by the end of 2026. Digital NEST has Centers in the heart of Watsonville, Salinas,  Gilroy and Modesto. The final Digital NEST Center is expected to launch in Stockton in the summer of  2024.



The Director of Learning and Evaluation plays a critical role in advancing the mission of Digital NEST by leading its efforts to measure, analyze, and report on the organization’s impact and effectiveness. This position is responsible for designing and implementing a comprehensive and culturally responsive evaluation system to ensure the effectiveness and impact of the organization’s programs to improve programmatic outcomes, which support enhanced life outcomes for the youth and young adults we serve in the 5 communities. This candidate will be passionate about bridging the digital divide and promoting inclusive workforce environments.

The Director will have expertise and awareness in and working knowledge of the needs of first-generation, low-income underrepresented youth and immigrant families, especially Latinx populations.  The Director will also have experience with developing equitable, culturally responsive evaluation methodologies reflecting the communities we serve to accurately and effectively inform data-driven decision-making, enhance program effectiveness, and provide actionable and timely findings for our staff and external partners in K-12/post-secondary education, philanthropic institutions, and workforce sectors/workforce development field.

The Director will also help to advance a culture of learning within the organization, working closely with all departments to demonstrate and understand organizational impact and what it means for members, community partners, and funders; enhance program development; inform organizational priorities; increase visibility and resources that will demonstrate our deepened impact in the communities we serve in the Monterey Bay Region and San Joaquin Valley. This position reports to the President and Chief Operating Officer (P/COO) and will work very closely with the Directors of Organizational Effectiveness, Systems and Programs.



Leadership, Design and Implementation (40%)

  • In Collaboration with the P/COO, set the vision and organizational strategy that will guide the creation and implementation of a robust evaluation system: the technology, frameworks, methodologies and the tools to measure the impact and effectiveness of the NEST Program and its branches, as well as organizational initiatives.
  • Design and develop evaluation tools, surveys, and instruments that are culturally affirming for diverse youth and communities and tailored to our specific contexts, as well as, accessible to the team to ensure data driven learning and application in real time.
  • Establish the evaluation metrics that align with the organizational strategic plan and funding objectives; a dashboard for use/monitoring across the organization; and develop the department’s playbook.
  • Ensure metrics align to data collection methods across the three program branches, with specific attention to areas, including, but not limited to, tools and measurements for all programs and events within the three program branches, with integration career navigation skill building across the branches.
  • Develop and maintain departmental policies and procedures, including deployment of data collection policies and practices.
  • Oversee the collection, management, and analysis of quantitative and qualitative data for evaluation and learning projects, ensuring the accuracy and validity of evaluation findings.
  • Collaborate with leadership and program staff to develop and refine the organization’s learning and workforce development strategies, as needed.
  • Provide leadership on team information to facilitate use of data and findings to inform key decisions and strategy execution.
  • Work closely with the finance team to develop an efficient budget for learning and evaluation initiatives that will maximize impact in the near term and forecast long-term budgetary needs.

Reporting, Monitoring and Quality Assurance (30%)

  • Prepare evaluation reports summarizing key findings, conclusions, and recommendations.
  • Prepare comprehensive annual impact reports to serve both internal and external stakeholders. Internally, to inform organizational strategic decision-making and to support the existing grant reporting and new grant submission opportunities. Externally, to inform external stakeholders of program impact.
  • Develop and effectively present emerging data trends and summative reports in user friendly language to inform real-time, decision-making and continuous improvement of the three branches of the Program. Identify areas for improvement and make recommendations for programmatic adjustments.
  • Increase understanding of and improve administration of data gathering tools; improve utilization of evaluation information and redefine progress from a community-oriented perspective.
  • Implement rigorous quality assurance measures and conduct quality checks to ensure uniform data collection compliance quality across the organization, while maintaining the highest evaluation standards and best practices.

Capacity Building and Technology (20%)

  • In collaboration with the Systems and Organizational Effectiveness Directors, assess the current system for evaluation purposes and make recommendations for a long-term plan.
  • Drive the coordination and collaboration with program leadership on a reporting schedule for the collection and dissemination of data, dashboards, and reports to HUB teams, Executive Team, Board of Directors, and other key stakeholders for use across the organization.
  • Work closely with the Development team to provide data needed for the grant-writing and grant-reporting processes.
  • Provide leadership and mentorship to staff involved in learning and evaluation activities.
  • Build the capacity of staff to engage in and implement program evaluation activities by conducting professional development trainings – developing user-friendly tools, offering technical support and mentoring/coaching as needed.
  • Develop learning resources and training materials for staff at all levels of understanding to create a culture of learning and knowledge sharing.
  • Integrate technology solutions into learning programs to enhance accessibility, engagement, and scalability.

Collaboration, Communication and Partnerships (10%)

  • Seek out state/federal/foundation grant opportunities to support a more robust evaluation program to explore the viability of implementing a longitudinal study.
  • Collaborate with the Marketing and Communications team to identify opportunities to disseminate findings of impact via social media channels.
  • Identify and pursue opportunities for strategic partnerships with leading statewide-national agencies that may enhance the organization’s reach and impact.
  • Develop white papers and present at key conferences to disseminate our approach as a viable solution to addressing the economic disparities and solutions for youth in rural communities.
  • Support the organization with other duties as assigned when needed.



  • Bachelor’s degree in a relevant field, such as education, social sciences, public policy or a field strongly related to the duties and responsibilities of this position.
  • At least 12 years of full-time, professional experience in nonprofits and/or the education or social science sector, program administration/management that is relevant to the role and communities served.
  • The cumulative equivalent of at least 7 years, full-time experience in program evaluation with a proven track record of building and leading evaluation systems and initiatives in the aforementioned sectors with a focus on equity.
  • Creative and innovative thinking with a strategic and growth mindset.
  • Experienced in leading/supervising high performing teams and cross-department collaboration.
  • Commitment to Digital NEST’s mission and working knowledge of the needs of first generation, low-income, immigrant families and underrepresented youth, especially Latinx populations.
  • Understanding of CREE principles (Culturally Responsive and Equitable Evaluation) and a commitment to racial equity.
  • Commitment to ethical and culturally responsive evaluation practices with a focus on equity.
  • Strong understanding of quantitative and qualitative research methods and data analysis techniques from an equity perspective.
  • Strong communication and presentation skills, with the ability to convey complex data and insights in a clear and compelling manner, with an emphasis on equity considerations.
  • Exceptional written and verbal communication skills.
    Proven leadership abilities with a track record of collaborating and project managing cross-functional teams.
  • Self-motivated and demonstrates capacity to organize projects to ensure time is spent on highest priorities.
  • Proficiency in evaluation software and tools (e.g., SPSS, NVivo, Qualtrics).
  • Exceptional project management skills, with the ability to manage multiple projects simultaneously.
  • Technological savvy with a willingness to embrace new technology.
  • Experience with managing relational databases and/or grants management platforms.


  • Master’s degree in a relevant field, such as education, social sciences, public policy or a field strongly related to the duties and responsibilities of this position.
  • Bilingual/biliterate English and Spanish


  • Passion for the mission of Digital NEST and belief in upholding organization’s core values.
  • Understanding of and sensitivity to issues of culture/ethnicity/race, gender, sexual identity, class/SES and immigration status.
  • Ability to be an ally to people of color, women and lesbian, gay, bisexual, transgendered, queer, questioning and intersex individuals and their allies (LGBTQIA).
  • Must have a valid CA driver’s license and be able to travel and work evenings or weekends occasionally, or as needed.
  • This position may involve domestic travel with overnight stays.

NOTE: The job offer will be contingent upon the successful completion and passing of a background check.


ABOUT OUR BENEFITS: We take a holistic approach to wellness, physical, emotional, and financial. Our comprehensive benefits package includes:

  • 100% Agency Paid Medical, Dental, Vision, and Life Insurance for the employee
  • SIMPLE IRA Retirement Benefit with up to 2% employer match
  • 10 Paid Vacation Days for Full-time Employees (non-Director and non-Chief positions)
  • 15 Paid Vacation Days for Full-time Employees (Director and Chief positions)
  • 13 Paid Holidays Annually Plus Business closure/holiday the week between Christmas Day and New Years Day
  • Paid Sick Time Off
  • Annual Parking Permit

We understand that no candidate is perfectly qualified for any job. Experience comes in different forms; many skills are transferable, and passion goes a long way. Even more important than your resume is a clear demonstration of dedication, impact, and the ability to thrive in a fluid and collaborative environment. We want you to learn new things in this role and encourage you to apply if your experience is close to what we’re looking for. We also know that diversity of background and thought makes for better problem-solving and more creative thinking, so we’re dedicated to adding new perspectives to the team. We look forward to hearing from you.

Digital NEST, Inc. is an equal opportunity employer and all qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by law.

Digital NEST is committed to an inclusive experience for all applicants and will endeavor to make reasonable accommodations in the interview process, to the known physical or mental limitations of qualified employees with disabilities unless the accommodation would impose an undue hardship on the operation of our business.  

Please refer to our career page for more information on how to apply for reasonable accommodations.

To apply for this job please visit

Nonprofit Connection Santa Cruz County is a 501(c)3 corporation, Federal Tax ID# 87-2130376

PO Box 1894
Soquel, CA 95073

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