Quality & Training Senior Manager

OAKLAND LEAF FOUNDATION•Oakland, CA

1d•Hybrid

About The Position

The Quality & Training Senior Manager owns Oakland Leaf's staff development infrastructure and program quality systems ensuring every staff member, from a first-year Program Instructor to a veteran Site Manager, has the training, tools, and support to do their job well and grow within it. This is not a training coordinator role. The Quality & Training Senior Manager operates at a systems level designing training scope and sequences, conducting cross-program observations, building quality assurance processes, and serving as a thought partner to Associate Directors on coaching and practice improvement. The right person understands that training is only as good as its connection to real practice and brings the instructional credibility, relational trust, and organizational skill to close that gap consistently across a multi-site program team.

Requirements

Strong commitment to Oakland Leaf's mission and belief in the power of youth leadership and equity in education
At least 3–5 years of experience in staff training, instructional design, program quality, or a closely related field with demonstrated experience designing and delivering professional development for frontline youth development or education staff
Strong understanding of positive youth development principles, social-emotional learning frameworks, and best practices in expanded learning programming
Experience conducting program observations and using structured feedback tools to support staff growth and program improvement
Demonstrated ability to build and maintain training systems and quality assurance processes across multiple sites or program contexts
Knowledge of California Quality Standards for Expanded Learning Programs and CDE compliance requirements for ASES, ELO-P, and 21st CCLC programs preferred
Excellent facilitation, coaching, and communication skills with the ability to build trust and credibility with staff at every level of the organization
Systems thinker with strong organizational and project management skills. Ability to manage a complex annual training calendar while staying responsive to emerging staff development needs
Experience working within or alongside OUSD or comparable urban public school systems a plus
Proficiency with Google Workspace, Microsoft Office Suite, and learning management or training tracking systems
Experience: 3–5 years in staff training, program quality, instructional coaching, or youth development program management; experience in expanded learning or out-of-school time programs strongly preferred
Education: Bachelor's degree in Education, Youth Development, Organizational Development, or related field preferred; equivalent experience considered; credentials in instructional design, coaching, or youth development a plus

Nice To Haves

Knowledge of California Quality Standards for Expanded Learning Programs and CDE compliance requirements for ASES, ELO-P, and 21st CCLC programs
Experience working within or alongside OUSD or comparable urban public school systems
Credentials in instructional design, coaching, or youth development

Responsibilities

Design and maintain a comprehensive training scope and sequence for all program roles ensuring clarity on what staff need to know, when they will learn it, and how mastery will be assessed
Own the annual training calendar: role-specific onboarding training, mid-year professional development, and refresher sessions including coordinating logistics, facilitators, and content in close partnership with Associate Directors
Develop onboarding pathways that go beyond paperwork ensuring every new staff member understands Oakland Leaf's values, program framework, youth development philosophy, and their role within the whole before they step into a site
Create training content that is culturally responsive, youth-centered, and grounded in Oakland Leaf's actual practice. Continuously evaluate training effectiveness using observation data, staff feedback, and outcome trends to refine content and delivery in real time
Develop and maintain observation and feedback tools that are specific, actionable, and developmental giving staff and their supervisors a shared language for what quality looks like in Oakland Leaf programs
Conduct regular structured site observations across programs not to evaluate staff directly, but to identify system-level patterns that inform training design, coaching priorities, and program support
Coordinate with Associate Directors to ensure observation cycles are happening consistently and that feedback is being used by staff and supervisors
Own and administer program quality surveys for both internal staff and external stakeholders including participants, families, and school partners, synthesizing findings into actionable insights that inform program improvement and organizational learning
Own Oakland Leaf's Quality Assurance process: establish clear quality benchmarks across program contexts, track them consistently, and report findings to the Director of Programs with concrete, actionable recommendations
Maintain alignment with California Quality Standards for Expanded Learning Programs ensuring Oakland Leaf's internal quality framework reflects and exceeds state expectations and supports CDE compliance
Serve as a thought partner and active resource to Associate Directors and Site Managers on staff coaching challenges providing frameworks, tools, and real-time support when staff development situations require it
Support the Director of Programs in building a coaching culture across the program team where feedback is normalized, growth is expected, and staff feel developed rather than evaluated
Facilitate communities of practice, peer learning sessions, and team reflection structures that build connection and shared learning across sites and program areas
Identify high-potential staff across program sites and surface those observations to Associate Directors and the Director of Programs contributing to Oakland Leaf's internal promotion pathway and succession planning
Partner with site leadership to support staff who are struggling including providing targeted coaching resources, observation support, and development plans in collaboration with the supervising coordinator or manager
Participate in and contribute to the monthly HR Operations Sync alongside the Office & People Operations Manager ensuring onboarding timelines, training compliance tracking, and staff development systems are integrated across HR and program functions
Partner with the Office & People Operations Manager to sequence and integrate the HR and program components of new hire orientation ensuring new staff experience a coherent, well-coordinated entry into Oakland Leaf
Maintain training compliance records across all program staff including tracking required certifications, mandated reporter training, first aid and CPR completion, and any CDE-required training hours
Support grant reporting and funder communications as they relate to staff development, training hours, and quality assurance data in partnership with the Director of Programs and Development