Senior Director, Chief of Staff to the CEO

Justworks; New York (NY); On-site; USD 240,000 - 274,000; Full time

Job summary

Justworks seeks a senior, AI-forward Chief of Staff to the CEO in New York City. You will partner with the CEO and executive team to accelerate company growth, refine operating models, and translate AI opportunities into practical changes that improve how we work and serve customers.

The role blends strategic judgment with hands-on execution, focusing on prioritization, cross-functional impact, and building organizational capabilities.

Qualifications

• 6+ years of experience in a Chief of Staff, strategy, business operations, consulting, product, operations, or transformation role.
• Strong strategic judgment and ability to translate priorities into action.
• Hands-on execution capability and senior leadership partnering.
• Ability to operate with CEO and executive team and influence across functions.
• Ability to translate AI opportunities into practical changes.

Responsibilities

• Become a trusted advisor to the CEO and contribute to executive team effectiveness.
• Translate strategy into clear execution plans and outcomes across the organization.
• Identify and drive AI-enabled operating transformations with cross-functional leaders.
• Align longer-term objectives with annual planning and resource allocation.
• Drive the executive operating rhythm, communications, and board reporting.
• Own high-impact strategic initiatives on behalf of the CEO and leadership team.

Skills

Strategic thinking

AI fluency

Results-driven

Influence & communication

Nimble learning

Customer focus

Speed & prioritization

Cross-functional collaboration

Job description

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 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, focused execution.

In addition, all Justworkers focus on aligning their behaviors to our core values known as COGIS. It stands for:

• Camaraderie - Day to day, you can be seen working together toward a higher purpose. You like to have fun. You’re an active listener, treat people respectfully, and strongly desire to know and help others.
• Openness - Your default is to be open. You're willing to share information, understand other perspectives, and consider new possibilities. You’re curious, ask open questions, and are receptive to thoughts and feedback from others.
• Grit - You demonstrate grit by having the courage to commit and persevere. You’re committed, earnest, and dive in to get the job done well with a positive attitude.
• Integrity - Simply put, do what you say and say what you'll do. You’re honest and forthright, have a strong moral compass, and strive to match your words with your actions while leading by example.
• Simplicity - Be like Einstein: “Everything should be made as simple as possible, but no simpler.”

Qualifications

• 6+ years of experience in a Chief of Staff, strategy, business operations, consulting, product, operations, or transformation role, with the judgment and range to operate effectively with a CEO and executive team.
• A track record of leading complex, cross‑functional initiatives from strategy through implementation and delivering meaningful business outcomes.
• Hands‑on experience using AI tools as a regular part of your work, plus 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
• Demonstrated 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.

This role is based in our New York City headquarters. The base wage range for this position will be $240,000 - $274,000 annually.

Actual compensation is based on multiple factors that are unique to each candidate, including and not limited to skill set, level of relevant experience, and specific work location. Salary ranges for positions based in other locations may differ based on the cost of labor in that location.

For more information about Justworks’ Total Reward Philosophy, including all of the perks and benefits we are proud to offer our team members, please visit Total Rewards @ Justworks .

Diversity At Justworks

Justworks is committed to maintaining a workplace where diversity of identity, culture, and life experience is the norm and is celebrated authentically and consistently. Diversity in our work, our people, and our product drives creativity and innovation, entrepreneurial leadership and integrity, competitiveness and collaboration throughout our business and in the market. We depend on our differences to make our team stronger, our workplace more dynamic, and our product accessible to all of our customers.

We’re proud to be an equal opportunity employer open to all qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or familial status, disability, pregnancy, gender identity or expression, veteran status, genetic information, or any other legally protected status. Justworks is fully dedicated to providing necessary support to candidates with disabilities who may require reasonable accommodations. We also provide reasonable accommodations to employees based on their sincerely held religious beliefs, as well as for other covered reasons consistent with applicable federal, state, and local laws. If you're in need of a reasonable accommodation, please reach out to us at [e-mail]. Your comfort and success matter to us, and we're here to ensure an inclusive experience.

Our DEIB Report