Full-time | Washington, DC | Reports to the Senior Vice President, Quality Coaching | Travel: 15–20%

Lead how technology can strengthen human-connected coaching

Strada Education Foundation's Quality Coaching team is working to expand access to quality education-to-career coaching. Its work is organized around three change drivers: Transition Coaching, strengthening guidance as learners move from high school into postsecondary education and employment; Postsecondary Education Quality Coaching, strengthening coaching within postsecondary institutions; and Statewide Quality Coaching Models, helping states expand access to quality coaching at scale.

Strada's Principles for Quality Education-to-Career Guidance emphasize outcomes, student agency, universal access, relationships, and the use of data and evidence. New technologies like AI offer cross-cutting capabilities that can strengthen these principles by expanding access and personalization, improving the use of labor market and outcomes information, and augmenting – rather than replacing – the human relationships central to quality coaching.

We are looking for a Senior Director who will lead Quality Coaching's Technology Innovation portfolio, building on Strada's existing research, investments, and partnerships to advance human-centered technology that augments human-connected coaching. The portfolio focuses on three key questions: (1) where and how technology can most effectively augment career coaching; (2) what quality standards and benchmarks should guide career navigation tools; and (3) what data systems and infrastructure are needed to support quality coaching at scale.

As a member of the Quality Coaching leadership team, you will also strengthen the entire portfolio by overseeing the team's Project Manager and providing strategic oversight for grants, impact measurement and learning, and teamwide project management. You will bring rigorous analysis, synthesis, and judgment to complex strategic questions and help translate strategy, evidence, and innovation into measurable impact.

What You'll Do

Lead Technology Innovation Strategy and Portfolio (60%) You'll develop and lead the strategy and portfolio that helps scale Quality Coaching's three change drivers. That means:

• Develop and lead Quality Coaching's Technology Innovation strategy and portfolio, defining priorities and use cases, investments, partnerships, measures of success, and other pathways to scale.
• Advance the Technology Innovation learning agenda by building evidence and actionable guidance about how technology can augment human-connected coaching and career navigation.
• Determine the quality standards and technical benchmarks that should guide technology-enabled career coaching tools.
• Understand the systems, data infrastructure, and appropriate roles for AI needed to support quality coaching at scale.
• Assess the career navigation technology ecosystem and identify promising solutions, capabilities, gaps, and emerging opportunities, to help Strada determine whether to partner, invest, or discontinue approaches.
• Translate research, investments, pilots, and field learning into practical frameworks and scalable approaches that help states, institutions, schools, and coaching organizations responsibly adopt and integrate human-centered technology.
• Serve as Strada's Quality Coaching subject-matter leader on technology and AI, partnering across other departments (Research, Strategy & Innovation, and Impact Investments) and with external partners to advance shared opportunities.
• Collaborate with Strada's Learner Engagement team to incorporate what students are saying about their lived experiences into the design, evaluation, and continuous improvement of tech-enabled coaching approaches.

Provide Strategic Analysis, Synthesis and Cross-Team Leadership (15%) Strong strategy depends on clear thinking and trusted relationships. You will:

• Independently frame and analyze complex strategic questions, drawing on research, data, portfolio learning, and partner perspectives to identify patterns, risks, opportunities, and next steps.
• Synthesize complex and incomplete information, shape initial responses to cross-functional and organizational requests, and drive issues toward resolution through clear options, tradeoffs, and decision-ready recommendations for the SVP, Quality Coaching and other senior leaders.
• Contribute as a member of the Quality Coaching leadership team, identifying connections across the three change drivers and leading cross-functional priorities through influence, clear decision-making, and accountability.
• Represent Strada with researchers, funders, policymakers, education leaders, and technology providers to share relevant learning through presentations, publications, partnerships, and convenings.
• Lead complex, cross-functional initiatives through influence, establishing clear roles, decision rights, and accountability across internal and external partners.

Advance Impact, Evidence and Portfolio Execution (15%) You'll help make sure good ideas turn into measurable results. You will:

• Provide strategic oversight for Quality Coaching's grants, contracts, and impact investments, working with cross-functional partners to strengthen portfolio coherence, grant development, implementation, learning, and decision-making.
• Coordinate Quality Coaching's approach to impact measurement and learning, partnering with Research and initiative leaders to establish clear outcomes, learning questions, measures of success, and evidence-building approaches and to translate findings into decisions.
• Manage and develop the Project Manager, Quality Coaching, providing strategic direction for teamwide project and portfolio management, annual planning, progress monitoring, grants coordination, budgets, and other operating systems.
• Provide light-touch project management leadership across Quality Coaching, ensuring visibility into major priorities, deliverables, dependencies, risks, resource needs, and decision points while maintaining clear accountability with initiative leaders for substantive strategy and results.
• Strengthen connections across the Quality Coaching portfolio by identifying patterns, shared learning, and opportunities that can improve execution and impact across initiatives.

Support Organizational Health and Culture (10%)

• Serve as an integrator across Quality Coaching, connecting perspectives and work across initiative leaders and coordinating strategic follow-through on shared priorities.
• Foster a collaborative, inclusive, and high-performing team culture grounded in Strada's board-approved principles, valued behaviors, and ways of working.
• Contribute to Quality Coaching and organization-wide efforts to strengthen organizational health, employee engagement, collaboration, inclusion, belonging, and continuous improvement.
• Support the development and success of colleagues through coaching, feedback, and knowledge sharing while contributing to shared accountability and collective success.

What Success Looks Like in Your First Year

• You are advancing a coherent Technology Innovation strategy and portfolio across Quality Coaching's three change drivers, with clear priorities, use cases, intended outcomes, and pathways for testing, learning, adoption, and scale
• You have generated actionable frameworks and insights addressing how technology augments human-connected coaching, quality standards and technical benchmarks for career navigation tools, and the systems, data infrastructure, and interoperability needed to support quality coaching at scale
• You have strengthened impact measurement and learning across Quality Coaching through clearer outcomes, learning questions, measures of success, and synthesis of evidence to inform strategy, investment, adaptation, and scale
• You have established effective oversight of Quality Coaching's grants and portfolio management, with clear visibility into major investments, priorities, deliverables, risks, dependencies, resources, and decision points
• You are successfully managing and developing the Project Manager and have established a light-touch PMO function that improves teamwide planning, coordination, accountability, and execution without displacing initiative-level ownership
• You are providing high-quality strategic analysis, decision support, and cross-team leadership by independently framing complex questions, producing decision-ready recommendations, and strengthening collaboration across Quality Coaching and Strada

What You Bring

Required:

• At least 8 years of progressively responsible experience in education technology, innovation, career coaching, student success, workforce development, philanthropy, strategy, and consulting, including significant responsibility for independently leading complex strategic initiatives.
• Demonstrated experience developing and executing technology- or AI-enabled strategies and translating innovative ideas into practical pilots, partnerships, investments, and scalable approaches, preferably involving education, coaching, advising, career navigation, or other learner-facing services.
• Strong portfolio leadership and execution skills, with experience overseeing complex portfolios, grants or investments, project-management systems, and progress monitoring from strategy through implementation, measurement, and learning.
• Highly independent strategic thinker and self-starter who can create structure amid ambiguity, frame and analyze complex questions, synthesize qualitative and quantitative information, assess alternatives and tradeoffs, distinguish signal from noise, and translate analysis into actionable recommendations.
• Exceptional synthesis, writing, communication, and presentation skills, with demonstrated ability to translate complex information into concise, compelling memos, analyses, recommendations, presentations, and board-level materials for technical and nontechnical audiences.
• Demonstrated experience defining measurable outcomes and learning questions and partnering with research or evaluation experts to use evidence to inform strategy, investment, adaptation, and scale.
• Demonstrated experience managing and developing staff and leading complex, cross-functional work by building trusted relationships and successfully advancing shared priorities in a distributed leadership team environment and in a matrixed organization.
• Experience managing consultants, grants, vendors, and external partnerships and leading teams and complex initiatives through influence, with a demonstrated commitment to developing others and strengthening team performance.
• Knowledge of responsible AI practices and the opportunities, limitations, and risks associated with using technology to serve learners, including privacy, accessibility, transparency, student agency, data interoperability, evidence, and the appropriate role of human relationships in coaching and career navigation.
• Demonstrated ability to cultivate, grow, and manage positive, mutually beneficial relationships at all levels of an organization and with partners outside the organization, with strong communication, interpersonal, and relationship management skills, underscored by strong judgment and emotional intelligence.

Nice to have:

• An advanced degree, with training in education, technology, innovation, business, public policy, social science, data and analytics, or a related field

Also important:

• Commitment to providing equitable pathways to opportunity through postsecondary education and training, particularly for individuals who have faced significant barriers, and demonstrated alignment with Strada's guiding values
• Demonstrated commitment to contributing to a collaborative, inclusive, and mission-driven culture: you value diverse perspectives and lived experiences, seek input from those affected by your work, collaborate effectively across organizational boundaries, and demonstrate curiosity, accountability, agility, stewardship, and continuous learning
• Personal attributes including: strategic problem solver, disciplined and creative mind, player-coach mentality, takes initiative and works independently, embraces ownership and responsibility, secure in sharing and receiving feedback, elevates the success of others, finds fulfillment in teaching and mentoring, eager learner, contagious enthusiasm, high integrity and commitment to accuracy, and committed to improving individual lives and our society

Why Strada

Strada Education Foundation is a national nonprofit dedicated to strengthening the connections between education and employment — with a particular focus on people who've faced the greatest barriers to economic opportunity through postsecondary education and training. Our strategic plan centers on five priorities: clear outcomes, quality coaching, affordable postsecondary education and training, work-based learning, and employer alignment.

We offer a dynamic, collaborative, and inspiring professional environment with robust opportunities to test innovative approaches and build evidence for impact at scale to improve education-to-career outcomes for millions of learners. We invest in our people the same way — with real learning and professional development opportunities, inside the organization and out.

Benefits

• Medical, dental, and vision insurance
• Generous PTO and paid holidays
• 401(k) retirement plan with employer contributions
• Paid parental leave
• Wellness reimbursement
• Professional development resources

Strada welcomes diverse candidates and values a wide range of backgrounds, experiences, and perspectives. Bringing together people with a variety of personal, educational, and professional experiences strengthens our understanding of the learners we serve, leads to better decisions, and enhances our mission impact. We encourage applicants who will enrich our workplace through their knowledge, skills, perspectives, and expertise.

 

By submitting this application, I certify that the information provided is accurate and complete to the best of my knowledge. I understand that any false statement, misrepresentation, or omission may disqualify me from consideration or result in termination if discovered after employment begins. Candidates who receive an offer of employment will be required to provide professional references and successfully complete a background check and education verification as a condition of employment.