Fast Facts

Join Pluralsight as a Chief of Staff for the Office of the CTO, where you will partner with the CTO to drive operational excellence and execute strategic initiatives in a fast-paced technology environment.

Responsibilities: Key responsibilities include partnering with the CTO on strategic priorities, leading cross-functional initiatives, coordinating leadership engagements, providing decision support, and representing the Office of the CTO.

Skills: Candidates should possess strong leadership, project management, analytical, and communication skills, along with the ability to influence across functions and handle sensitive information.

Qualifications: Preferred qualifications include 10+ years of experience in technology strategy or operations, particularly in large-scale or complex organizations, and experience supporting C-level executives.

Location: This is a remote role, but applicants within 45 miles of Westlake/Dallas, TX should expect to work on-site Tuesday through Thursday, with remote flexibility on Mondays and Fridays.

Compensation: $115300 - $160100 / Annually

Job Description:

The Chief of Staff is a strategic partner to the Chief Technology Officer, responsible for driving operational excellence and enabling the effectiveness of the Office of the CTO. This role provides critical support in shaping and executing the technology strategy, ensuring cross-functional alignment and overseeing high impact initiatives.

In this role, you will coordinate strategic planning, operational reviews and leadership team engagements to ensure clarity of priorities and accountability for results. You will also act as an extension of the CTO in preparing for board meetings, partner engagements and stakeholder interactions.

This position is critical for fostering collaboration across the enterprise, providing decision support and enabling the CTO to focus on the most critical priorities. They will bring strong business acumen, organizational agility and a high tolerance for ambiguity to operate effectively in a dynamic and fast-paced environment.

Who you’re committed to being:

• You enjoy learning and are open to new ways of doing things.
• You are not afraid to be yourself, experiment, make mistakes and learn from them, ask questions, or voice your concerns.
• Relationship building is at your core and you use that ability to gain alignment and deliver results.
• You are a professional with strong communication and presentation skills.

What you’ll do:

• Partner with the CTO to define, communicate, and execute the technology organization’s strategic priorities and roadmap.
• Lead and manage cross-functional initiatives, ensuring delivery against scope, timeline, and outcomes.
• Coordinate leadership team meetings, offsites, and board engagements to drive alignment, accountability, and follow-through.
• Provide decision support through data analysis, insights, and preparation of executive materials for the CTO.
• Act as a liaison between the CTO, senior leadership, and external stakeholders to ensure effective communication and follow-up.
• Identify and drive process improvements to increase operational efficiency within the technology organization.
• Support change management and organizational readiness for technology-driven initiatives.
• Represent the Office of the CTO in select forums, ensuring consistent messaging and alignment with organizational objectives.

Experience you’ll bring:

• 10+ years of progressive experience in technology strategy, operations, consulting, or related roles.
• Experience in large-scale, global, or complex organizational environments is preferred.

Requirements:

• Demonstrated experience supporting C-level or senior technology executives in a strategic or operational capacity.
• Strong leadership and project management skills with the ability to advance multiple high-priority initiatives simultaneously.
• Exceptional analytical, problem-solving, and critical thinking skills.
• Strong written and verbal communication skills with proven ability to influence and build relationships across functions.
• High integrity, discretion, and ability to manage sensitive and confidential information.
• Collaborative, adaptable, and comfortable operating in an environment of ambiguity and change.
• This is a remote role; however, applicants located within 45 miles of our Westlake/Dallas, TX office should expect to work on-site Tuesday through Thursday, with remote flexibility on Mondays and Fridays. This approach enables more effective collaboration, quicker decision-making, and a stronger culture, while still providing flexibility.

Why you’ll love working here:

• We’re a blended workplace, where team members work remotely or in a hybrid setup depending on their role and location
• We’re mission driven and guided by our culture pillars
• We have a strong commitment to diversity and belonging
• We cultivate a culture of trust, autonomy, and collaboration
• We’re lifelong learners and champion team member growth and advancement
• We’ve got you covered - team member benefits include competitive compensation packages, medical coverage, unlimited PTO, wellness reimbursements, Pluralsight subscription, professional development funds and more.

About us:

Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today’s tech workforce. Thousands of companies, government organizations and individuals around the world rely on Pluralsight to support critical technology skill development in areas that are crucial to innovation including artificial intelligence, cloud computing, cybersecurity, software development, and machine learning. Pluralsight provides highly curated content developed by vetted technology experts, industry leading skill assessments, and hands on, immersive learning experiences designed to help individuals skill-up faster.

Physical Requirements:

This role is primarily performed in an office or home office setting and involves standard computer-based work.

EEOC Statement & Accommodations Statement:

Bring yourself. Pluralsight is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, or veteran status. We also consider qualified applicants with criminal histories, consistent with EEOC guidelines and local laws.

If you need an accommodation to apply, interview, or perform essential job functions, please visit the bottom of our website to learn how to request an accommodation. Learn more about our commitment to diversity, equity, inclusion, and belonging in our DEIB Report.

The annual US base salary range for this role is $115,300 - $160,100 USD. Actual compensation will depend on location, skills, experience, and other factors. Additional benefits and bonuses may apply.

Applications must be submitted within 90 days after the initial posting date to be considered.

Please be aware of recruiting scams. We’ll only contact you from an @pluralsight.com email or verified channels. We never ask for sensitive personal info or payments as part of the hiring process. All openings are posted on our Careers page.

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