Senior Director - Chief of Staff & Strategic Operations Leader

Role Description

We are seeking an experienced, highly strategic Chief of Staff and Strategic Operations Leader to serve as a key partner to senior leadership in scaling and optimizing a large, complex organization of approximately 500 employees. This role goes beyond traditional operational support. The Chief of Staff will help shape organizational strategy, drive execution against business priorities, and establish the planning, governance, and operating frameworks that enable teams to scale effectively.

The ideal candidate is a systems thinker, exceptional problem solver, and influential leader who thrives in ambiguity, challenges conventional thinking, and continuously seeks innovative ways to improve organizational efficiency. As a trusted advisor to leadership, this individual will play a meaningful role in aligning strategy to execution, ensuring resources are focused on the highest-value work, and driving cross-functional collaboration across the organization and its key partners.

Responsibilities

• Lead strategic planning and execution by partnering with senior leadership to translate business strategy into roadmaps, priorities, governance, and measurable outcomes across a 500-person organization.
• Drive organizational design and workforce strategy through headcount planning, budgeting, organizational effectiveness, operating model evolution, and talent planning in partnership with Finance and HR.
• Advise executives and lead strategic programs by managing cross-functional initiatives, facilitating executive decision-making, and developing data-driven business cases and recommendations.
• Champion operational excellence by improving planning processes, business rhythms (QBRs/QBOs), governance, metrics, and scalable operating models that accelerate execution and productivity.
• Enable cross-functional alignment by coordinating Product, Engineering, Sales, Customer Success, Finance, and HR to manage dependencies, align priorities, and ensure execution remains focused on customer and business outcomes.

Qualifications

• 10+ years of experience in strategic operations, management consulting, business transformation, Chief of Staff, program leadership, or similar strategic roles.
• Demonstrated success supporting large, complex organizations (300+ employees preferred) through periods of growth, transformation, or scale.
• Proven ability to influence senior executives and drive alignment across diverse stakeholder groups without direct authority.
• Strong experience in organizational planning, workforce strategy, operating model design, portfolio management, and strategic execution.
• Outstanding critical thinking, problem-solving, and analytical capabilities with the ability to navigate ambiguity and make data-driven recommendations.

Preferred Qualifications

• Experience leading large-scale cross-functional initiatives involving multiple teams and business functions.
• Outstanding executive communication and storytelling skills, including development of board-level and executive-level content.
• Strong business acumen with the ability to balance strategic thinking and execution.
• Demonstrated ability to challenge existing processes and introduce innovative approaches that improve organizational performance.

Benefits

• Medical, dental and vision insurance.
• 401(k) plan with a Cisco matching contribution.
• Paid parental leave.
• Short and long-term disability coverage.
• Basic life insurance.
• 10 paid holidays per full calendar year, plus 1 floating holiday for non-exempt employees.
• 1 paid day off for employee’s birthday, paid year-end holiday shutdown, and 4 paid days off for personal wellness determined by Cisco.
• Non-exempt employees receive 16 days of paid vacation time per full calendar year.
• Exempt employees participate in Cisco’s flexible vacation time off program.
• 80 hours of sick time off provided on hire date and each January 1st thereafter.
• Optional 10 paid days per full calendar year to volunteer.