Senior Director of People Operations

Careerwise Colorado•Glendale, CO

40d•$93,000 - $138,000•Hybrid

About The Position

CareerWise is a nationally-recognized nonprofit organization that creates life-changing opportunities for the youngest generation of America’s workforce. We build industry-led, student-centered, modern youth apprenticeships through classroom and on-the-job learning, providing flexible, alternative pathways to economic mobility. As our programs have launched in multiple states, we are leveraging our institutional knowledge, technology, and infrastructure to scale our impact. We are seeking an operational leader who can strategically guide and manage all People Operations functions for a rapidly growing organization. You are a proactive thought partner, a structured problem-solver, and a highly organized leader who excels at translating strategic vision into high-impact processes and programs. You bring executive-level HR and operations management experience, a deep commitment to Diversity, Equity, and Inclusion (DEI), and the ability to inspire, guide, and develop a high-performing HR team. Reporting directly to the Chief of Staff and People Operations, the Senior Director of People Operations will lead the execution of the organization's comprehensive HR strategies, ensuring seamless operations across all CareerWise markets (Colorado and New York City). This role will directly supervise the Director of Human Resources and is responsible for talent acquisition, performance management, employee experience, and HR technology. You will ensure that all people's systems and policies are aligned, compliant, and supportive of a vibrant, inclusive workplace culture.

Requirements

Deep knowledge of HR best practices and demonstrated experience leading a hybrid/distributed workforce, cross-functional projects, and change management initiatives.
Proven ability to serve as an objective, strategic thought partner to executive leadership.
Operates with the highest level of integrity and maintains strict confidentiality.
Exceptional critical thinking and analytical skills to break down complex problems and drive solutions.
Demonstrated commitment to DEI principles and proven experience advancing them in the workplace.
Proven ability to build trusting relationships with senior leaders and staff at all levels.
Highly organized, with the ability to prioritize and execute multiple high-stakes priorities on tight deadlines.
Comfort with change and ambiguity, thriving in a fast-paced, rapidly changing environment.
Self-motivated with a proven record of establishing and scaling systems and processes where none currently exist, providing structure to an evolving organizational landscape.

Responsibilities

Serve as a key thought partner to the Chief of Staff, proactively analyzing internal data and industry best practices to identify strategic opportunities and develop compelling, data-informed recommendations for organizational design, talent strategy, and operational excellence.
Execute and operationalize the HR strategies, including talent acquisition, performance management, upskilling, and culture initiatives.
Drive the operationalization of strategic priorities, translating high-level goals into concrete, measurable projects, timelines, and resource plans.
Serve as a key leader within People Operations, ensuring all practices uphold the highest level of integrity and align with the organization's mission and goals.
Appraise and align HR policies, procedures, and systems across locations (Denver, CO, and New York City, NY), guiding staff through change management processes.
Collaborate with the Executive Leadership Team (ELT) on strategic staffing plans, providing input on optimal hiring approaches and compensation strategy.
Support the Director of Human Resources, ensuring effective day-to-day HR function across employee relations, compliance, and core HR services.
Provide high-level guidance and support on complex employee relations issues and workplace investigations, ensuring all actions are unbiased, legally sound, and consistent with company policy.
Oversee the management and optimization of all People Operations technology, including HRIS, Payroll, ATS, and employee engagement platforms.
Ensure all HR policies, procedures, and standards adhere to federal, state (Colorado and New York), and local employment laws, with a strong emphasis on multi-state and remote work compliance.
Lead the development and execution of strategies to effectively onboard, engage, and support a multi-state remote workforce.
Lead efforts to cultivate a vibrant, inclusive workplace culture that promotes wellness, engagement, and success.
Oversee the strategic design and delivery of employee development and upskilling programs to ensure staff growth and high performance.
Drive continuous improvement in the performance management system, ensuring consistency and effectiveness across all departments.
Develop and present key metrics and performance insights to the Chief of Staff and ELT, monitoring the progress of strategic people initiatives and recommending necessary course corrections.
Foster strong relationships with internal and external stakeholders to advance organizational priorities and effectively communicate change.