Chief of Staff - CTO

Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details. About the Opportunity The organization was launched with a mission to provide universal access to world-class learning. Today, it is one of the largest online learning platforms in the world, with millions of registered learners. The organization partners with over 375 leading university and industry partners to offer a broad catalog of content and credentials, including courses, Specializations, Professional Certificates, and degrees. The platform innovations — including generative AI-powered features like Coach, Role Play, and Course Builder, and role-based solutions like Skills Tracks — enable instructors, partners, and companies to deliver scalable, personalized, and verified learning. Institutions worldwide rely on the organization to upskill and reskill their employees, students, and citizens in high-demand fields such as GenAI, data science, technology, and business, while learners globally turn to the organization to master the skills they need to advance their careers. The organization is a public benefit corporation and a B Corp. The hiring company is committed to building a globally diverse team and is thrilled to extend employment opportunities to individuals in any country where the organization has a legal entity. Candidates are required to possess eligible working rights and have a compatible timezone overlap with their team to facilitate seamless collaboration. As a remote-first company, interviews and onboarding are entirely virtual, providing a smooth and efficient experience for candidates. Job Overview A Chief of Staff is sought to join the team and serve as a strategic integrator for the Chief Technology Officer, operating across a major function or business domain to connect strategy and execution. This role ensures that the Tech organization scales effectively, translating company strategy into a cohesive operating system that drives alignment, accountability, and results across multiple teams. The organization is evolving how it operates to enable sustained growth and agility. The Chief of Staff plays a central role in that evolution, designing and improving the frameworks that underpin performance, including planning, governance, decision-making, and resource allocation. Operating at the intersection of strategy and operations, this role enables the executive and leadership team to deliver the organization’s goals with greater clarity, speed, and discipline. Objectives of this role: Translate company strategy into functional operating systems that connect priorities, plans, and execution across teams Drive cross-functional alignment within and adjacent to the Tech organization, ensuring shared accountability for results Design and evolve frameworks that bring structure, discipline, and visibility to planning, goal-setting, and performance tracking Enable high-quality decision-making through data, narratives, and governance models that clarify tradeoffs and resource allocation Ensure organizational readiness and adaptability, balancing scale with speed as the organization continues to evolve Strengthen the leadership system within the Tech org, increasing focus, follow-through, and clarity across teams Responsibilities: Manage and continuously improve the CTO Org operating rhythm, including timely review and action of key performance indicators (KPIs) Partner with executive-enabling functions - People, Finance, Administration - to drive CTO’s strategic change and improvement initiatives org-wide Drive the strategic and operational planning system for the CTO organization, defining and continuously improving processes that enable the CTO to effectively and efficiently manage their large team with ongoing visibility into results and impact Oversee a portfolio of strategic projects, structuring and driving to completion complex, ambiguous initiatives, steering large, cross-functional projects, and building consensus with senior leadership across the organization Lead employee engagement strategy, in collaboration with People Business Partner, crafting initiatives that foster a positive, inclusive, and dynamic work environment. Plan and execute internal communications within the team, ensuring that all team members are informed, aligned, and motivated Create cross-functional connections between the principal’s org and adjacent functions to accelerate decision-making and remove friction Facilitate strategic meetings, ensuring alignment and clarity on objectives, and drive follow-through on action items. Represent the COO in certain cross-functional meetings and projects, advocating for their priorities and ensuring alignment with overall company strategy Build and develop relationships with the CTO’s direct reports and other individuals in critical roles - providing an unbiased ear - to understand the need and opportunities in existing ways of working and helping define new strategies to address Required Qualifications: 12-15 years in a business or executive management role In-depth experience driving results in an Engineering organization Extremely versatile, dedicated to efficient productivity Experience defining, planning, and driving top-level strategic initiatives Excellent communicator in written and verbal form Demonstrated experience organizing and directing multiple teams and departments Proven track record of data-driven approach to complex decision-making Preferred Qualifications: Master’s degree in Business Administration or similar field Experience with data analysis Experience with budget management Consulting experience with a focus on operations management Proven success in a project management role Nimble business mind with a focus on developing creative solutions Strong project reporting skills, with a focus on interdepartmental communication Compensation: This role is available in the following US Pay Zones: US Zone 1: $188,480 - $235,600 US Zone 2: $180,120 - $225,150 US Zone 3: $167,200 - $209,000 US Zone 4: $155,420 - $194,275 The organization offers competitive, zone-based pay aligned to location, experience, and role level across four U.S. pay zones. The total rewards package goes beyond salary, with comprehensive health and wellness benefits, bonus and RSU equity programs, and global perks designed to help individuals grow and thrive wherever they are. US Pay Zones: US-Z1: Bay Area US-Z2: NYC and Seattle Metro US-Z3: CA, WA, NY, NJ, CO, CT, DC, GA, IL, MA, MD, OR, RI, TX, VA US-Z4: AK, AZ, DE, FL, HI, ID, IN, IA, KS, KY, MI, MN, MO, MT, NC, NV, NH, OH, OK, PA, SC, TN, UT, VT, WI The hiring company is an Equal Employment Opportunity Employer and considers all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, age, marital status, national origin, protected veteran status, disability, or any other legally protected class.