Senior Director of Operations at CareerWise

Who we are:  

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. We have hundreds of CareerWise apprentices in the workplace, charting new paths to academic and career success. In addition, workforce and education leaders from across the country have visited CareerWise to learn about our youth apprenticeship model. As a result, our programs have launched in multiple states, leveraging our institutional knowledge, technology, and infrastructure.  

Who We’re Looking For: 

We’re seeking a mission-driven Senior Director of Operations to partner closely with CareerWise’s COO in making big ideas real. This role is for a seasoned operator who thrives on turning strategy into action, building systems that create clarity, and keeping complex projects moving forward. You’re the kind of person who loves when processes run smoothly, communication is clear, and goals are met. With 10+ years of nonprofit operations experience, you bring the steady hand, strategic mind, and problem-solving instincts needed to make our work more effective and impactful.

Job Summary:

Reporting to the COO, the Senior Director of Operations serves as the execution arm of CareerWise’s operational strategy. This leader will manage cross-functional projects, streamline internal systems, and build processes that ensure accountability and alignment. Acting as a hub for operations, the Senior Director will support strategic planning, monitor progress against goals, and drive solutions to operational challenges.

The role is remote however there will be occasional travel to Denver, New York City, and Washington, DC offices.

What You’ll Be Doing:

• Strategic Planning & Execution

  • Partner with the COO to translate strategy into clear, actionable plans.

  • Facilitate strategic discussions across teams to align efforts with organizational goals.

  • Build dashboards, reports, and presentations to track and communicate progress.

  • Monitor strategic initiatives, surface roadblocks, and recommend solutions.

• Operational Leadership & Systems Design

  • Identify opportunities to improve workflows and implement best practices.

  • Develop and document operational processes that create clarity and consistency.

  • Represent the COO in internal meetings to advance operational priorities.

  • Create systems that ensure visibility, accountability, and alignment across teams.

• Project Management

  • Lead cross-functional projects from planning through execution.

  • Define project scope, set timelines, manage budgets, and track milestones.

  • Serve as the hub for issue resolution, ensuring projects move forward smoothly.

  • Support flagship operations by identifying challenges and streamlining workflows.

• Collaboration & Communication

  • Build strong relationships with leaders and staff across all departments.

  • Ensure operational decisions and updates are clearly communicated across the organization.

  • Act as a connector between the operations team, consulting team, and flagship staff.

• May perform other duties as assigned.

Key competencies to be successful in this role:

• Ability to advance and execute operational strategy in complex, multi-stakeholder environments.

• Skilled at creating systems that bring clarity and accountability across functions.

• Strong judgment and ability to balance big-picture strategy with detailed execution.

• Ability to design and manage projects that integrate seamlessly into team workflows.

• Resourceful and adaptable when navigating roadblocks and shifting priorities.

• Deep belief in organizational mission and the ability to rally others to achieve it.

• Comfortable leading from the center of the action, providing steady guidance during times of change.

Additional Proficiencies:

• 10+ years of progressive experience in nonprofit operations management (required).

• Demonstrated success in strategic planning, project management, and process improvement.

• Strong reliance on data and comfort in making data-informed decisions.

• Exceptional written and verbal communication skills, able to convey complex ideas simply.

• Experienced in Microsoft Office and Google Suite. Bonus if you have exposure to Slack, Monday.com, Salesforce, or LucidSpark.

• Comfortable managing high-stakes projects and supporting leadership in external presentations and reporting.

• Skilled collaborator who thrives in cross-functional environments and fosters positive team culture.

The above statements are intended to describe the essential functions of the job being performed by employees assigned to this classification. The duties listed are not to be construed as an exhaustive list of all responsibilities, duties, and skills required. All employees may be required to perform duties outside of their normal responsibilities from time to time, as needed. With the evolution of the organization and this role, the responsibilities of this position may change at any time.

Location:

This role can be remote or based in either of our flagship offices located in New York, NY and Denver, CO. CareerWise staff typically work a hybrid schedule with Tuesday, Wednesday, and Thursday in the office and other days remote. Remote work is not guaranteed and the schedule must be approved by the supervisor. There may be occasions (possibly 1-3 times per year) for staff to gather together in person. Exceptions will be made for special circumstances.

Compensation:

The starting salary range for this role is: $93,094 to $138,586 annually; this role is not covered by the minimum wage and overtime provisions of the FLSA. CareerWise offers a generous benefits package including group medical, dental, and vision plans, short-term disability, 100% vested 401k plan with a 3% employer contribution, and flexible time off.

How to Apply:

Please upload your resume with a cover letter letting us know why you are interested in working at CareerWise along with what specific experience you have that uniquely qualifies you for this position. We are excited to review your application materials!

Application Window:

CareerWise anticipates the application window closing approximately 30 days from the date this notice was posted. However, factors such as candidate flow and business necessity may require CareerWise to shorten or extend the application window.

CareerWise is an Equal Opportunity Employer and Prohibits Discrimination and Harassment of Any Kind: CareerWise is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at CareerWise are based on business needs, job requirements, and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. CareerWise will not tolerate discrimination or harassment based on any of these characteristics. CareerWise encourages applicants of all ages. CareerWise is committed to building a diverse staff and encourages applications from people of color. If you need assistance or accommodation due to a disability, you may contact us at: [email protected]