Chief of Staff

About the role

The Chief of Staff serves as a trusted execution partner, helping leaders translate priorities into action and ensuring strategic initiatives move from concept to measurable results. This is a highly collaborative, relationship-oriented role that influences through trust, diplomacy, and operational excellence rather than direct authority.

Responsibilities

• Lead the planning and execution of strategic initiatives by developing project plans, defining milestones, tracking progress, and ensuring alignment with organizational priorities.
• Persistently partner with leaders across departments to drive cross-functional collaboration, remove obstacles, and ensure successful execution of business objectives.
• Carefully coordinate leadership operating rhythms, including recurring meetings, agendas, action items, and follow-up activities that support organizational effectiveness and accountability.
• Support organizational change initiatives by helping leaders implement new processes, improve ways of working, and drive adoption of operational improvements.
• Identify and proactively address execution risks, organizational challenges, and cross-functional dependencies, escalating issues and recommending solutions when needed.
• Collaborate with leaders to establish meaningful performance metrics, improve reporting processes, and translate data into actionable insights and recommendations.
• Provide decision-making support for key initiatives by facilitating planning discussions, evaluating options and tradeoffs, documenting decisions, and ensuring clear communication of next steps.
• Lead special projects from concept through implementation, defining success measures, testing solutions, and delivering measurable business outcomes.

Requirements

• Educated. Bachelor’s degree in business or a related field required; MBA or equivalent graduate degree preferred. 8–12+ years of experience in business operations, management consulting, and program leadership required. Experience with ERISA regulatory requirements, Taft-Hartley pension / health and welfare plans, and vendor contracting is a plus.
• Strategic Partner. Demonstrated ability to build strong relationships, leading cross-functional delivery without formal authority (stakeholder management, influencing, and disciplined follow-through).
• Effective Communicator. Strong written and verbal communication: can create clear executive and stakeholder updates, decision frameworks, and meeting materials.
• Data fluent. Comfortable working with analytics and systems teams. Familiar with the use of AI to support workflows and data analysis.

Qualifications

• Ethical and Credible. Low-ego, high-accountability operator with resilience, discretion, and strong follow-through; trusted with sensitive information and able to earn confidence across long-tenured teams while still driving needed change.

Skills

• Strong stakeholder management and influence skills.
• Ability to work collaboratively across departments.
• Experience with ERISA regulatory requirements, Taft-Hartley pension / health and welfare plans, and vendor contracting is a plus.
• Comfortable working with analytics and systems teams.
• Familiarity with using AI to support workflows and data analysis.

Benefits

• Starting salary range of $15,400 - $20,840 per month. Pay is dependent on experience, skills, and qualifications.
• Excellent Medical, Dental (w/Ortho), Vision, Rx benefits, disability, life insurance
• Optional benefits include health flex spending & dependent care assistance plans, pet insurance
• Paid Vacation (10 days), Sick Leave (10 days) and Holidays (10 days)
• Generous 401k plan with company base contribution & match
• Work-Life Balance

Pay

• Starting salary range of $15,400 - $20,840 per month. Pay is dependent on experience, skills, and qualifications.

Schedule

• Full time