
Executive Chief of Staff
Swooped · United States
- Hybrid
- Full-time
- $150,000 / year
- United States
Job highlights
- Partner directly with CEO and ELT.
- Drive strategic initiatives and execution.
- Own cross-functional operating rhythm.
- Leverage AI for efficiency and insights.
- Handle sensitive information with discretion.
About the role
About the Opportunity
The companies that define the next decade will be the ones who learned to move faster, decide smarter, and execute with precision—AI at the core. The organization is building that company now, and the Executive Chief of Staff is how it gets there. In this role, you will sit at the intersection of strategy, transformation, and execution—partnering directly with the CEO and Executive Leadership Team to drive the initiatives that accelerate growth, unlock efficiency, and shape the future of work. You will own the cross-functional operating rhythm that keeps the business moving, and you will do it with the judgment and discretion that comes from being trusted with things that matter. This is high-speed, high-visibility, and high-impact—and it demands someone who can take a complex problem, drive it independently through to a decision, and return with a clear output. If that’s the environment where you do your best work, the team wants to meet you.Key Responsibilities
Independent Initiative Ownership
- Own high-impact strategic initiatives end-to-end—from scoping and alignment through execution and measurable business results. You drive the work, not the calendar.
- Translate executive priorities into clear, AI-enabled execution plans across functions—with the autonomy to make calls and move without constant direction.
- Identify execution risks early and deploy mitigation strategies using predictive insights and scenario modeling. Surface what matters; resolve what you can before it lands on the CEO’s desk.
- Design and track KPIs that tie initiatives directly to revenue, efficiency, and profitability—owning the accountability loop, not just the reporting layer.
Operating Cadence & Cross-Functional Execution
- Own and drive the organization’s cross-functional operating cadence—QBRs, executive rhythms, leadership forums, and the connective tissue that keeps a fast-moving business aligned and accountable.
- Orchestrate cross-functional teams to deliver faster, with tighter feedback loops and real-time visibility. You are the force multiplier that unblocks decisions and moves work forward.
- Build AI-powered operating systems—dashboards, copilots, workflows—that increase the speed and quality of decision-making across the ELT.
Executive Partnership & Storytelling
- Partner with the ELT to prepare board materials, CEO updates, and investor narratives using AI-assisted synthesis—turning complex data and dynamics into clear, high-stakes communications.
- Support the storytelling of the business in a transformative year of AI-native product and company evolution. Help the CEO communicate with clarity, credibility, and confidence internally and externally.
Change Management & Organizational Navigation
- Act as a trusted partner to the CEO through periods of organizational change—helping design, sequence, and land transformational decisions in ways that stick.
- Help the ELT navigate the human side of change: communication, sequencing, stakeholder alignment, and the difference between a decision that’s made and one that’s actually adopted.
- Serve as a connective bridge across functions—building trust with leaders, surfacing misalignments before they become problems, and modeling the operating culture the organization is building toward.
Judgment, Discretion & Confidentiality
- Exercise exceptional judgment about what to act on, what to escalate, and what to hold—recognizing that proximity to sensitive information is a trust, not a tool.
- Handle commercially sensitive data, executive dynamics, personnel decisions, and investor-level information with the discretion expected of someone operating at the most senior level of the organization.
- Know when to be visible and when to work quietly behind the scenes. Influence without overstepping. Move without leaving a wake.
Required Qualifications
- 5–7 years in strategy consulting, SaaS operations, private equity value creation, or similar high-intensity environments—with a track record of owning outcomes, not just supporting them.
- Demonstrated ability to take complex, ambiguous workstreams from problem definition through to a clear decision or output—independently, without requiring structure to be built around you.
- Exceptional judgment: you know what to escalate, what to resolve, and what to hold in confidence. You’ve earned trust by being the person who handles sensitive situations with maturity.
- Change management experience—you understand that transformation is as much about people and sequencing as it is about strategy. You’ve helped organizations navigate hard decisions, not just document them.
- Strong operator mindset—you advise and execute, owning outcomes end-to-end. Coordination and synthesis are the floor, not the ceiling.
- High AI fluency—experience using GenAI, automation tools, and data systems to accelerate workflows and insights. You build with AI, not just use it.
- Sharp analytical thinking—you translate data into clear decisions and action, and you can hold a financial model, a SaaS metric, and an executive narrative in your head at the same time.
- Executive presence—you communicate with clarity, influence senior stakeholders, and build trust quickly, even when you’re the least experienced person in the room.
- Strong financial and SaaS metric literacy—you understand how decisions impact ARR, NRR, EBITDA, and the Rule of 40, not just in theory but in context.
- A “Love to Win” attitude—you operate from a desire to see success, not a fear of failure. You bring pace, optimism, and resilience to hard problems.
- Comfort in ambiguity—you bring structure, speed, and focus to complex problems, and you don’t wait to be told what to do next.
Why This Role?
- High-Performance Culture: The organization believes in the power of accountability, focus, and drive. The A-Player team members work together to deliver measurable, meaningful results. Excellence is recognized and rewarded.
- Ownership and Accountability: Employees are trusted to take full ownership of their roles, providing the autonomy to innovate and the support to succeed. Individuals who are self-motivated and thrive in an environment where they can drive impactful outcomes are sought.
- Technology-Forward: As an organization invested in cutting-edge technology, AI and other advanced solutions are integrated across the platform to enhance productivity, customer experience, and process efficiency. Team members are excited by the potential of AI and proactively explore ways it can drive success.
- Growth Mindset: Continuous learning and improvement are integral to the culture. The team is encouraged to embrace challenges, seek knowledge, and develop both personally and professionally.
- Innovation and Agility: A dynamic, fast-paced environment where fresh ideas and bold solutions are celebrated. Change is embraced and challenges are turned into opportunities, with a team that is agile, proactive, and resilient.
- Collaborative, Results-Driven Environment: Purposeful collaboration that leads to shared success and stronger results is valued. While team members are independent, they recognize the value of working together to drive the mission forward.
- Competitive Benefits and Rewards: Comprehensive and competitive benefits packages are offered globally, designed to support the team’s health, well-being, and financial security. Investment is made in people so they can excel.
Key skills/competency
- Executive Chief of Staff
- Strategy Consulting
- SaaS Operations
- Private Equity Value Creation
- AI Fluency
- Change Management
- Analytical Thinking
- Executive Presence
- Financial Literacy
- Project Management
Skills & topics
- Executive Chief of Staff
- Strategy Consulting
- SaaS Operations
- AI
- GenAI
- Change Management
- Executive Leadership
- Strategic Initiatives
- Operations Management
- Business Transformation
How to get hired
- Tailor your resume: Highlight 5-7 years of experience in consulting, SaaS ops, or PE value creation, emphasizing outcome ownership.
- Showcase AI fluency: Detail your experience with GenAI and automation tools in driving workflows and insights.
- Demonstrate judgment: Provide examples of handling complex, ambiguous situations and sensitive information with maturity.
- Quantify impact: Use data and metrics to illustrate your success in driving revenue, efficiency, and profitability in previous roles.
- Prepare for strategy discussions: Be ready to discuss your approach to change management, executive partnership, and cross-functional execution.
Technical preparation
Master GenAI and automation tools.,Understand SaaS metrics and financial models.,Develop data analysis and synthesis skills.,Practice building AI-powered workflows.
Behavioral questions
Describe handling ambiguity and driving results.,How do you manage sensitive information?,Share an example of leading change.,How do you partner with senior executives?
Frequently asked questions
- What is Swooped's role in the hiring process for the Executive Chief of Staff position?
- Swooped is a Talent Platform and is not the employer for this role. Clicking 'Apply' will direct you to Swooped to review the role and hiring company details. Swooped does not make hiring decisions.
- What level of AI proficiency is required for the Executive Chief of Staff role?
- High AI fluency is required. This includes experience using GenAI, automation tools, and data systems to accelerate workflows and insights. You should be comfortable building with AI, not just using it.
- What kind of experience is expected for the Executive Chief of Staff position?
- The role requires 5-7 years in strategy consulting, SaaS operations, private equity value creation, or similar high-intensity environments, with a proven track record of owning outcomes independently.
- How does the Executive Chief of Staff role contribute to the company's growth?
- The Executive Chief of Staff drives initiatives that accelerate growth, unlock efficiency, and shape the future of work by partnering with the CEO and ELT, owning strategic projects, and optimizing the operating cadence.
- What are the key leadership qualities needed for this Executive Chief of Staff role?
- Exceptional judgment, discretion, change management experience, a strong operator mindset, sharp analytical thinking, executive presence, financial and SaaS metric literacy, a 'Love to Win' attitude, and comfort in ambiguity are crucial.
- Will I be working directly with the CEO in this Executive Chief of Staff position?
- Yes, this role involves partnering directly with the CEO and the Executive Leadership Team to drive strategic initiatives and manage the cross-functional operating rhythm.
- What does 'owning outcomes' mean for the Executive Chief of Staff at this company?
- Owning outcomes means taking full responsibility for strategic initiatives from scoping and alignment through execution and measurable business results, driving the work independently and delivering clear outputs.