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Swooped

Chief of Staff to the Founder

united states / Posted
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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 is scaling rapidly and has a growing pipeline of opportunities that demand exceptional talent across disciplines. The mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help realize this next chapter of growth.


This is a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate individuals from feedback or basics. Critique is invited, learning happens quickly, and the bar is continuously raised. The best ideas win here, no matter where they come from, because clients trust the organization to deliver the strongest outcomes every time.


Clients' missions, products, and bottom lines are sacred. The organization immerses itself in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset created must be both beautiful and functional; practical, usable, and designed for real-world impact.


Humans are the most valuable resource, and growth only happens by hiring people who push the organization forward. Across strategy, engineering, design, data, and operations, the organization seeks out teammates who raise the bar and make everyone better. Always hire up, never down.


The organization partners with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. The belief is that AI should amplify human potential, not replace it, and this conviction guides every engagement. From advisory and tooling to implementation and education, the organization meets clients where they are at and helps them integrate AI in ways that align with their mission and values. The goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.


And through it all, the organization leads with purpose, love, and adventure. Meaningful work is done with people who care about each other, and the ride is made an adventure worth taking. Because at this organization, who we are and how we work are one and the same.


The Opportunity

The organization is seeking an exceptional Chief of Staff to serve as a force multiplier to the founder. This role will be the engine that translates the founder's vision and initiatives into executable plans, builds the systems that allow the leadership team to operate at their highest level, and ensures nothing critical falls through the cracks as the organization scales rapidly.

Rather than being hired for a predetermined set of tasks, the individual will be brought on to solve complex, evolving challenges. Success in this role requires self-direction, proactive value creation, and the ability to thrive without constant oversight.


Over the coming year, responsibilities will be tailored to both organizational needs and individual strengths, potentially including:

  • Leading AI transformation projects with clients
  • Managing CEOs at client organizations
  • Driving sales initiatives for the organization
  • Partnering with Recruiting to help find and close top-tier talent
  • Managing client project delivery
  • Driving value through data and analytics for clients
  • Leading go-to-market initiatives for clients


This role will own special projects, drive organizational initiatives from concept to completion, and build the infrastructure (GTM motions, resource allocation, operational rhythms) that allows the organization to grow while maximizing its greatest strength – its people. If the candidate thrives on turning ambitious ideas into reality and building the scaffolding that makes a fast-growing startup actually work, this is the role.


Key Responsibilities

Strategic Execution & Founder Partnership

  • Partner with the founder to translate priorities, initiatives, and strategic vision into sequenced plans with clear owners, timelines, and success metrics
  • Own end-to-end execution of founder-level special projects and organizational initiatives, from scoping and planning through delivery and measurement
  • Maintain focus and accountability across the founder's portfolio of priorities; proactively identify conflicts, dependencies, and risks before they become problems
  • Prepare high-quality executive materials (strategy briefs, decision memos, board materials, organizational roadmaps) that drive alignment and enable confident decision-making
  • Serve as a strategic thought partner to the founder, pressure-testing ideas, surfacing options and trade-offs, and ensuring initiatives align with company strategy and capacity


Internal Systems & Operations

  • Build and continuously improve the internal operating systems that allow the organization to scale: hiring infrastructure, resource allocation processes, team capacity planning, and cross-functional coordination mechanisms
  • Design and implement hiring systems that support the organization's growth target without overwhelming the existing team, including interview frameworks, candidate evaluation rubrics, and onboarding processes
  • Own resource allocation and capacity planning across the organization, ensuring the right people are working on the right priorities at the right time, and that no one is stretched unsustainably thin
  • Establish organizational rhythms that create alignment without bureaucracy: leadership meeting cadences, decision-making frameworks, communication protocols, and reporting structures
  • Identify operational bottlenecks and inefficiencies; design and implement solutions that increase organizational velocity while maintaining quality


Cross-Functional Leadership & Coordination

  • Orchestrate complex, cross-functional initiatives that require coordination across leadership and multiple teams
  • Serve as a neutral coordinator and problem-solver when initiatives span multiple departments or require difficult trade-offs between competing priorities
  • Represent the founder's office in key internal discussions, ensuring the founder's priorities and perspective are understood even when they cannot be in every meeting
  • Build strong working relationships across the organization; earn trust as someone who gets things done without ego and acts in the organization's best interest


Communications & Organizational Transparency

  • Ensure crisp internal communication on company strategy, priorities, and decisions—translating founder-level thinking into clear, actionable guidance for the broader team
  • Prepare the founder for key meetings, presentations, and decisions; provide relevant context, background materials, and recommended talking points
  • Maintain visibility on organizational health metrics and key initiatives; proactively surface issues and opportunities to leadership


Who You Are

Experience & Skills

  • 5-7+ years in high-performing environments such as Chief of Staff roles, strategic operations, management consulting, venture capital/private equity, business development, or startup leadership positions
  • AI-native, not AI-curious. Before doing almost anything manually, the individual has already asked themselves whether AI can do it better. Constantly tinkering, building small tools, automating personal workflows, and sharing findings.
  • Demonstrated success in taking ambiguous, complex initiatives and driving them to completion; the person who makes hard things happen
  • Strong systems thinking and process design capability; not just executing tasks, but building the infrastructure that makes future execution easier and more scalable
  • Exceptional project management and coordination skills across multiple concurrent work-streams with competing priorities and timelines
  • High proficiency with modern collaboration tools (Google Workspace, Asana/Notion, Slack) and intermediate to advanced comfort with AI-powered productivity tools
  • Outstanding written and verbal communication; ability to synthesize complex information into clear, actionable briefs for different audiences
  • Bonus: Experience in high-growth startups, venture studios, or AI/tech companies; background in talent operations or organizational design; proven success driving business development in B2B environments; exposure to board-level strategy and operations


Mindset & Traits

  • Mission-driven operator with deep commitment to the organization's values and vision
  • Systems builder, not just task executor, thinking about sustainable processes, not one-off solutions
  • High agency and bias for action, seeing what needs to happen and making it happen without waiting for permission
  • Calm under pressure with excellent judgment about when to escalate vs. solve independently
  • Ego-free collaborator who earns trust through delivery, not title or authority
  • Intellectually curious with strong learning agility, comfortable moving between strategic thinking and tactical execution
  • Comfortable operating in ambiguity, thriving when there's no playbook and creating clarity from complexity


Considerations

  • Education: Bachelor's degree or equivalent experience; an advanced degree in a relevant field is a plus


  • Ethics: Commitment to ethical practices and responsible business operations


  • Travel: Occasional (10–25%) for company offsites, key events, and leadership meetings


  • Location: Remote-friendly with preference for candidates in major tech hubs and strong preference for overlap with EST business hours


The hiring organization is an equal opportunity employer committed to building a diverse and inclusive team.