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Swooped logo

Chief of Staff Director

Swooped
Posted 2 days ago
🇺🇸United States🏠Remote💰$255.0K–$335.0K📁Operations & Admin
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About the Opportunity

The organization is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest.


About the People team

The People team helps individuals cultivate a high-performing, inclusive organization. The team focuses on three core areas: attracting talent aligned to the organization's mission, enabling growth through people and team development, and retaining employees through thoughtful experiences and rewards. The team develops the organization's people programs and systems to create a workplace where all employees can thrive and contribute meaningfully. By investing in people, the organization creates a long-term advantage for the business.


About the role

The Director, Chief of Staff will directly support the Chief People Officer and serve as a trusted advisor, thought partner, and strategic operator for the People organization. This role will work closely with the CPO and People leadership team to define priorities, sharpen strategy, create clear narratives, and drive execution across a broad, complex, and highly cross-functional organization.


The ideal candidate is an analytical, strategic, and self-directed operator who brings strong judgment, humility, discretion, and ownership to work that ranges from highly strategic to highly operational. The Director, Chief of Staff will help operationalize the People agenda, run organizational cadences, prepare executive-ready content, manage critical initiatives, and help the CPO and People leadership team anticipate challenges, surface insights, and connect dots across the organization.


Success in this role requires executive presence, exceptional communication skills, strong business judgment, and the ability to build deep trust with senior leaders. The right candidate will quickly develop a strong understanding of the organization's business, people strategy, operating model, and organizational dynamics, using that context to influence effectively, operate independently, and help the People organization move with clarity, alignment, and impact.


Key Responsibilities

  • Serve as a thought partner and trusted advisor to the Chief People Officer. Help the CPO pressure-test priorities, evaluate tradeoffs, anticipate challenges, surface insights, and make high-quality decisions with the right context.
  • Shape the People organization’s strategic narrative. Partner with the CPO to articulate the team’s strategy, priorities, progress, tradeoffs, and impact in a way that is clear, compelling, and grounded in business context and organizational outcomes.
  • Drive clarity and execution against People organization priorities. Help partner with the People Leadership Team and initiative owners to define, communicate, and advance the People team’s most important initiatives, ensuring leaders have the context, alignment, and follow-through needed to execute effectively.
  • Run the People organization’s operating rhythm. Manage key organizational cadences, including leadership team meetings, offsites, annual planning, business reviews, and other forums that enable effective decision-making and execution.
  • Prepare executive-ready content for key audiences. Develop high-quality presentations, narratives, leadership updates, and decision support for the CPO and People organization.
  • Act as connective tissue across the People leadership team and sub-teams. Improve information flow, surface risks and dependencies, identify decision bottlenecks, and help ensure leaders are operating with shared context, clear ownership, and aligned priorities.
  • Own special projects from problem definition through execution. Take on high-priority, ambiguous, confidential, or time-sensitive projects on behalf of the CPO, independently structuring the work, driving analysis, aligning stakeholders, and delivering outcomes.
  • Represent the CPO’s voice and priorities in cross-functional forums. Exercise sound judgment on when to make decisions, escalate issues, seek input, or drive work forward independently.


Required Qualifications

  • 10+ years of experience in business management, HR/People strategy, Chief of Staff, or related roles, preferably in high-growth technology, fintech, or other complex operating environments.
  • Demonstrated understanding of how People organizations operate, including the core functions within a People team, the responsibilities and priorities of those functions, and how they work together to support the business and employee experience.
  • Experience operating as a strategic partner, trusted advisor, or thought partner to executive leadership, ideally supporting a Chief People Officer or another senior enterprise leader.
  • Exceptional storytelling and synthesis skills, with the ability to turn complex, cross-functional inputs into clear narratives, executive-ready materials, and compelling communications.
  • Highly self-directed, with strong judgment, discretion, and ownership; able to operate independently in a senior executive environment, handle sensitive matters, and know when to drive forward, seek input, or escalate.
  • Strong structured problem-solving and analytical skills, with the ability to break down ambiguous issues into clear options, tradeoffs, and recommendations.
  • Excellent communication skills, the ability to influence without formal authority, and to convey complex ideas succinctly.
  • Strong operational discipline, with a track record of managing complex cross-functional workstreams from strategy through execution.
  • Strong business acumen, with the ability to connect People priorities to the organization’s business, operating model, strategic priorities, and organizational needs.
  • A proven ability to use AI tools to raise the quality, depth, and impact of the work. This includes synthesizing large, cross-functional inputs, pressure-testing analysis, and generating executive-ready materials, paired with the judgment to know when to rely on AI and when not to.


Compensation and Benefits

  • Base Pay Grade - S
  • Equity Grade - USA 11
  • Employees new to the organization typically come in at the start of the pay range. The organization focuses on providing a simple and transparent pay structure which is based on a variety of factors, including location, experience and job-related skills.
  • Base pay is part of a total compensation package that may include equity rewards, monthly stipends for health, wellness and tech spending, and benefits (including 100% subsidized medical coverage, dental and vision for you and your dependents.)
  • USA base pay range (CA, WA, NY, NJ, CT) per year: $255,000 - $335,000
  • USA base pay range (all other U.S. states) per year: $226,000 - $306,000
  • Visa sponsorship is not available for this position.


Work Environment

The organization is proud to be a remote-first company! The majority of roles are remote and you can work almost anywhere within the country of employment. Individuals in proximal roles have the flexibility to work remotely, but will occasionally be required to work out of their assigned office. A limited number of roles remain office-based due to the nature of their job responsibilities.


The organization is extremely proud to offer competitive benefits that are anchored to its core value of people come first. Some key highlights of the benefits package include:

  • Health care coverage - The organization covers all premiums for all levels of coverage for you and your dependents.
  • Flexible Spending Wallets - generous stipends for spending on Technology, Food, various Lifestyle needs, and family forming expenses.
  • Time off - competitive vacation and holiday schedules allowing you to take time off to rest and recharge.
  • ESPP - An employee stock purchase plan enabling you to buy shares of the organization at a discount.


The organization believes It’s On Us to provide an inclusive interview experience for all, including people with disabilities. The organization is happy to provide reasonable accommodations to candidates in need of individualized support during the hiring process.


For U.S. positions that could be performed in Los Angeles or San Francisco, the organization will consider for employment qualified applicants with arrest and conviction records.


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

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