Senior Director, Chief of Staff to the CEO

Justworks•New York, NY

1d•$240,000 - $274,000•Onsite

About The Position

Justworks is seeking a senior, AI-forward Chief of Staff to partner with the CEO and executive team as the company accelerates its growth, operations, and customer service. The role contributes to the company’s cross-company transformation as AI changes how work gets done, combining strategic judgment with hands-on execution. The Chief of Staff will help the CEO focus on high-impact work, turn company priorities into coordinated action, and translate AI opportunities into practical changes to workflows and organizational capabilities. The position is intended to last at least two years, after which the person should be ready to take on a more senior role within the company. The role is based at Justworks’ New York City headquarters and requires working from the office five days per week. The stated annual base wage range is $240,000–$274,000. Actual compensation may vary based on factors including skills, relevant experience, and work location.

Requirements

At least 6 years of experience in a Chief of Staff, strategy, business operations, consulting, product, operations, or transformation role, with the judgment and range to work effectively with a CEO and executive team.
Track record of leading complex, cross-functional initiatives from strategy through implementation and delivering meaningful business outcomes.
Hands-on experience using AI tools regularly at work, along with a clear point of view on how AI can improve workflows, decision-making, and organizational effectiveness.
Strong analytical skills and business acumen.
Excellent written and verbal communication skills.
Ability to build productive relationships, influence senior stakeholders, and handle confidential or sensitive matters with discretion and sound judgment.
Ability to work from the New York City office five days per week.

Responsibilities

Serve as a trusted advisor to the CEO and help improve the effectiveness of the CEO and executive team; evolve the Chief of Staff role to provide maximum leverage to the CEO.
Help teams translate strategy into clear execution plans and outcomes, and bring leaders together to resolve issues between functional boundaries.
Partner with the CEO, Chief People Officer, and functional leaders to identify and deliver cross-functional AI-enabled improvements, from problem definition and workflow redesign through development, adoption, and measurement.
Partner with the CEO, CFO, Head of Strategy, and functional leaders to connect long-term objectives with annual planning, resource choices, and near-term execution.
Drive the company’s operating cadence and leadership-team rhythm to build shared understanding, support timely decisions, and drive accountability.
Improve how company strategy, learning, and execution are synthesized, captured, and reported to the Board; communicate complex information clearly for that audience.
Lead complex, high-impact special initiatives for the CEO and executive team, including urgent issues or opportunities that do not fit within a single function.
Steward the evolution of Strategy & Operations by shaping its talent strategy, developing roles and career paths, and growing its capabilities to meet business needs.
Use AI actively in personal work and build or test workflows and tools where useful; help teams adopt approaches that improve speed, quality, or customer outcomes.
Maintain customer impact in view when making decisions about priorities.