Chief of Staff

Swayable

• $140K — $160K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2-5 years of management or strategy consulting experience
  • Proven ability to manage complex projects for senior stakeholders
  • Strong organizational skills with a focus on accuracy
  • Excellent writing and communication skills
  • Comfortable with data analysis and presentation tools
  • Ability to build trust and exercise sound judgment
  • Thrives in fast-paced, ambiguous environments

Responsibilities

  • Drive strategic projects from inception to completion
  • Own tracking of executive team projects and priorities
  • Run leadership meeting cadence and document decisions
  • Produce high-quality executive deliverables like board decks
  • Identify inefficiencies and improve operational processes
  • Lead special projects to create leverage for executives
  • Coordinate events to strengthen company culture and communication

Benefits

  • 100% Medical, Dental & Vision Plans with no employee contribution
  • Generous PTO
  • Equity Options
  • 401k plan and FSA
  • Investments in ongoing professional development
Full Job Description
About The Role:

We're looking for a Chief of Staff to help our executive team turn strategic priorities into results. Working closely with the CEO, Chief Growth Officer, Chief Revenue Officer, and Head of Finance, you'll own cross-functional projects, executive deliverables, and the systems that keep our leadership team aligned and accountable.

This is an opportunity for someone with 2-5 years of management or strategy consulting experience who wants to move into a fast-paced startup environment, and take direct ownership of execution. You'll gain exposure to decisions across growth, revenue, finance, and company strategy, with meaningful responsibility from day one and room to take on an increasing scope over time.

What You'll Do:
  • Drive strategic projects from start to finish. Translate executive priorities into clear work plans, coordinate stakeholders, and own timelines, deliverables, and follow-through across growth, revenue, finance, and operations.
  • Own executive team project tracking. Maintain a clear view of company priorities, milestones, owners, and dependencies. Proactively remove blockers, flag risks, and ensure decisions turn into action.
  • Run the leadership operating cadence. Prepare agendas and materials for leadership meetings, document decisions, and drive follow-up. Coordinate quarterly planning, OKRs, and progress reviews to keep teams aligned.
  • Produce high-quality executive deliverables. Own the development of board decks, investor updates, strategic presentations, and company communications, working with executives to gather inputs and turn them into clear, compelling materials.
  • Improve how the company operates. Identify inefficiencies across departments and build practical processes that improve communication, clarify ownership, and help teams execute as the business grows.
  • Create leverage for the CEO and executive team. Lead special projects such as investor diligence, strategic hiring, and partnership initiatives. Prepare leaders for important meetings and represent their priorities in select internal and external discussions.
  • Help strengthen company culture and communication. Coordinate all-hands meetings, team events, and other moments that connect employees to Swayable's priorities and build excitement around our work.

Who You Are:
  • You have 2-5 years of experience in management or strategy consulting, with experience managing complex projects and delivering work for senior stakeholders.
  • You combine structured thinking with hands-on execution. You're excited to take a project from an initial question through analysis, recommendations, and implementation.
  • You're highly organized and dependable, able to manage competing priorities while maintaining a high standard for accuracy and follow-through.
  • You're an excellent writer and communicator who can turn complex information into concise presentations, clear recommendations, and actionable plans.
  • You're comfortable working with data, building analyses, and using spreadsheets and presentation tools to support business decisions.
  • You build trust across teams, exercise sound judgment with sensitive information, and can drive progress forward.
  • You thrive in ambiguity, learn quickly, and take initiative when you see something that needs to get done.
  • You're excited to move into a fast-paced startup, work closely with executive leadership, and grow through meaningful ownership and responsibility.

Benefits:
  • 100% Medical, Dental & Vision Plans - no employee contribution required
  • Generous PTO
  • Equity Options
  • 401k plan, FSA
  • Ongoing professional development investments
  • Compensation: $140-160K, dependent on experience

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