Senior Director, Chief of Staff to the CEO

Justworks · New York, New York

  • Senior
  • Full-time
  • Posted 2026-11-09
  • Confirmed live on 10 November 2026

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Job description

Who We Are

At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people.

We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you.

We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team.

Our Values

If this sounds like you, you’ll fit right in.

Who You Are

Justworks is seeking a senior, AI-forward Chief of Staff to the CEO. You will partner with the CEO and executive team as we accelerate how the company grows, operates, and serves customers. As AI changes how work gets done, you will be a key contributor to our ongoing cross-company transformation.

This role combines strategic judgment with hands-on execution. You will help the CEO focus on the highest-impact work, turn company priorities into coordinated action, and translate AI opportunities into practical changes to ways of working and organizational capabilities. The right person is a trusted advisor, a strong cross-functional operator, and a robust thinker who can move from enterprise-level considerations to the tactical details required to make progress.

The intention is that you would be in this role for at least 2 years and, through this experience, become ready to take on a more senior role within the company.

Your Success Profile

What You Will Work On

• CEO partnership: Become a trusted advisor to the CEO. Contribute to making the CEO more effective for the executive team, and the executive team more effective for the CEO. Evolve the CoS role as necessary to provide maximum leverage to the CEO & enable the CEO to focus on the highest impact activities.

• Enterprise priorities: Enable teams to translate strategy into clear execution plans and outcomes. Bring leaders together to resolve issues that are stuck between functional boundaries.

• AI-enabled operating transformation: Partner with the CEO, Chief People Officer, & functional leaders to identify where AI can materially improve how work gets done. Take selected cross-functional opportunities from problem definition and workflow redesign through development, adoption, and measurement.

• Strategic planning and alignment: Partner with the CEO, CFO, Head of Strategy, and functional leaders to connect longer-term objectives with annual planning, resource choices, and near-term execution.

• Executive operating rhythm: Drive the operating cadence of the business. Manage the operational rhythm of our leadership team with the goal of building shared consciousness, making timely decisions, and driving accountability.

• Board and executive communications: Reimagine how we synthesize, capture, and report on company strategy, learning, & execution for the Board. Distill complex information into clear thinking and messages tailored to that audience.

• Special initiatives: Own complex, high-impact work on behalf of the CEO and executive team, including urgent issues or opportunities that do not fit neatly within one function.

• Strategy & Operations stewardship: Own the evolution of Strategy & Operations as a capability by shaping its talent strategy, developing roles and career paths, and ensuring its capabilities grow with the needs of the business.

How You Will Do Your Work

As Senior Director, Chief of Staff, how results are achieved is paramount for your success and ultimately result in our success as an organization. In this role, your foundational knowledge, skills, abilities and personal attributes are anchored in the following competencies:

• Strategic mindset: See the broader business context, anticipate implications, and form recommendations even amidst ambiguity.

• AI fluency and builder mindset: Use AI actively in your own work, personally build or test workflows and tools where useful, and help teams adopt approaches that improve speed, quality, or customer outcomes.

• Results-driven: Take ownership from problem definition through implementation, maintain momentum, and deliver measurable outcomes.

• Influence and communication: Build trust with senior leaders and teams, communicate with clarity, and move work forward without relying on formal authority.

• Nimble learning: Learn unfamiliar domains quickly, seek input, test assumptions, and adapt as evidence changes.

• Customer focus: Keep the impact on customers in view when making decisions about priorities.

• Speed and prioritization: Accelerate organizational momentum by pairing decisive prioritization with fast, focus

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