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Chief of Staff

💰 $120,000 - $250,000

ExecutiveOperationsStrategy

🎯 Role Definition

The Chief of Staff (CoS) partners closely with the CEO and executive leadership to translate high-level strategy into executable plans, remove barriers to progress, and ensure organizational alignment. The CoS acts as a force-multiplier for the CEO: managing priority initiatives, coordinating cross-functional programs, preparing board and investor materials, and representing the CEO in meetings to accelerate decision-making and execution. This role requires a blend of strategic thinking, operational rigor, executive communication, and high emotional intelligence.


📈 Career Progression

Typical Career Path

Entry Point From:

  • Director of Operations / Head of Operations
  • Senior Program Manager / Director of Strategy
  • Chief Operating Officer (Deputy) / Director of Corporate Development

Advancement To:

  • Chief Operating Officer (COO)
  • Chief Strategy Officer (CSO)
  • General Manager / Business Unit Leader
  • CEO (startup / scale-stage)

Lateral Moves:

  • Head of Corporate Strategy
  • Head of Program Management Office (PMO)
  • Head of Investor Relations / Corporate Affairs

Core Responsibilities

Primary Functions

  • Act as a strategic partner to the CEO by synthesizing complex information, framing strategic options, and recommending clear decisions and next steps to accelerate company priorities.
  • Lead cross-functional, high-impact strategic initiatives from ideation to execution, including setting timelines, defining success metrics, coordinating stakeholders, and removing obstacles to delivery.
  • Own the CEO’s weekly operating cadence: manage meeting agendas, prioritize topics, track action items, and ensure timely follow-through across executive and functional teams.
  • Drive quarterly and annual planning processes, including goal-setting (OKRs/KPIs), resource prioritization, cross-functional dependencies mapping, and progress reviews with leadership.
  • Prepare, edit, and present executive-level materials — investor updates, board decks, strategy documents, and all-hands presentations — ensuring clarity, data-driven storytelling, and alignment to company objectives.
  • Serve as a trusted proxy for the CEO in internal and external forums, representing company priorities to senior leaders, partners, and investors while preserving confidentiality and trust.
  • Facilitate executive decision-making by conducting deep analysis, synthesizing stakeholder input, outlining trade-offs, and drafting decision memos that enable rapid alignment.
  • Design and maintain critical management processes (e.g., executive scorecards, risk registers, escalation frameworks) that improve transparency, cadence, and operational rigor across the organization.
  • Lead post-merger integration, major change initiatives, or strategic pivots by coordinating cross-functional teams, setting milestones, and tracking outcomes to ensure value capture.
  • Build and manage a prioritized portfolio of strategic projects, allocating resources, monitoring budgets, and reporting progress against defined milestones and ROI expectations.
  • Identify systemic issues affecting organizational performance, propose scalable solutions (process, people, tools), and partner with functional leaders to implement improvements.
  • Drive talent planning and organizational design discussions with HR and senior leadership to ensure the right structure, roles, and capability gaps are identified and addressed.
  • Partner with Finance to model scenarios, evaluate strategic investments, and translate financial outcomes into operational plans that balance growth and profitability.
  • Monitor market, competitive, and regulatory trends; synthesize implications for strategic planning and recommend proactive moves to capitalize on opportunities or mitigate risks.
  • Manage time-sensitive, confidential projects such as special investigations, executive transitions, or high-stakes negotiations, ensuring discretion and clarity of outcomes.
  • Coordinate investor relations activities, including due diligence preparation, fundraising support, and investor communication follow-ups, to maintain credibility and momentum.
  • Lead or partner on corporate communications for critical announcements, ensuring alignment across legal, HR, and product teams and minimizing execution risks.
  • Establish and run the executive operating model for scaling organizations — defining meeting rhythms, escalation paths, decision rights, and governance to drive faster, clearer outcomes.
  • Coach and mentor senior leaders and direct reports to build cross-functional collaboration skills, increase accountability, and foster a high-performance leadership culture.
  • Translate CEO vision into functional roadmaps and runnable plans for Product, Engineering, GTM, and Operations, ensuring clarity on dependencies, timelines, and owners.
  • Own escalation management for blockers that impede company priorities: triage issues, convene the right stakeholders, and drive to resolution within compressed timeframes.
  • Conduct executive-level stakeholder management across external partners, customers, and community leaders to remove friction and enable strategic partnerships.
  • Oversee special projects such as new market entries, pilot programs, and internal incubators — designing experiments, setting success metrics, and scaling winners.
  • Maintain a continuous improvement mindset: gather feedback on executive processes, iterate on tools and templates, and scale best practices across the organization.

Secondary Functions

  • Manage administrative and operational support for the CEO’s office including calendar optimization, travel planning for strategic trips, and prioritization of competing requests.
  • Support talent acquisition for key leadership roles by participating in hiring committees, defining role requirements, and conducting executive-level interviews.
  • Collaborate with People & HR to operationalize culture initiatives, performance management cycles, and leadership development programs tied to strategic priorities.
  • Partner with Legal and Compliance to ensure board materials, contracts, and strategic initiatives align with regulatory and governance expectations.
  • Support ad-hoc research and investor diligence requests with structured summaries, data pulls, and narrative framing to accelerate fundraising or M&A processes.
  • Maintain institutional knowledge and historical decision logs that enable faster onboarding of new leaders and continuity of strategic initiatives.
  • Facilitate leadership retreats, offsites, and cross-functional workshops to align teams around priorities and accelerate team dynamics.
  • Oversee vendor relationships tied to strategic programs (consultants, research firms, agency partners), negotiating scope and ensuring delivery against objectives.
  • Coordinate crisis response planning and execution, serving as a control point for communications, resource allocation, and stakeholder updates during incidents.
  • Manage operational dashboards and executive reports that provide near-real-time visibility into business performance and early warning indicators.

Required Skills & Competencies

Hard Skills (Technical)

  • Strategic planning and operational execution: proven ability to translate strategy into measurable plans, roadmaps, and milestones.
  • Program and project management: experience owning complex cross-functional initiatives with clear delivery frameworks (e.g., Agile, SCRUM, PMO practices).
  • Data analysis and synthesis: strong Excel/Sheets modeling, comfort interrogating dashboards (Tableau/Looker/Power BI) and producing executive summaries.
  • Financial literacy and modeling: ability to build scenario models, understand P&L drivers, and work with Finance on budgeting and forecasting.
  • Executive communications and storytelling: experience drafting board materials, investor decks, and high-stakes executive presentations.
  • Process design and change management: skill in designing scalable processes (decision rights, RACI, SOPs) and driving adoption across teams.
  • Tools fluency: proficiency with Google Workspace/Microsoft Office, Slack, Notion/Confluence, project management tools (Asana/Jira/Trello), and CRM basics (Salesforce).
  • Vendor and partner management: experience managing external advisors, consultancies, or boutique firms through procurement to delivery.
  • Risk and compliance awareness: familiarity with corporate governance, basic legal/compliance considerations, and confidentiality protocols.
  • Basic technical literacy: ability to partner with Engineering/Product teams, understand product roadmaps, and translate technical constraints into business plans.

Soft Skills

  • Executive presence and discretion: trusted to handle highly confidential information with professionalism and sound judgment.
  • Exceptional written and verbal communication: clear, concise, persuasive writing and presentation skills tailored to senior stakeholders.
  • High emotional intelligence: ability to read complex interpersonal dynamics and influence without direct authority.
  • Problem-solving and structured thinking: comfort breaking down ambiguous problems into hypotheses, analyses, and recommended actions.
  • Facilitation and convening: proven ability to run efficient meetings, workshops, and decision-making forums that generate alignment.
  • Prioritization and time management: expert at triaging competing priorities for the CEO and the leadership team.
  • Stakeholder management and diplomacy: experience balancing competing interests across functions, investors, and external partners.
  • Adaptability and resilience: thrives in fast-changing environments and can pivot priorities responsively while maintaining quality.
  • Coaching and team development: ability to mentor leaders and build leadership capability across teams.
  • Attention to detail with a bias for action: rigorous about follow-through and delivering polished outputs under tight deadlines.

Education & Experience

Educational Background

Minimum Education:

  • Bachelor’s degree in Business, Finance, Economics, Management, Public Policy, or related field.

Preferred Education:

  • MBA or advanced degree in a relevant discipline preferred but not required; or equivalent experience in high-growth startups or management consulting.

Relevant Fields of Study:

  • Business Administration
  • Strategy / Management
  • Finance / Economics
  • Public Policy / International Relations
  • Computer Science or Engineering (for product- or tech-heavy environments)

Experience Requirements

Typical Experience Range:

  • 6–12+ years of progressive experience in operations, strategy, program management, management consulting, or corporate development; including 2–5 years supporting C-suite leaders or operating at the executive level.

Preferred:

  • 8+ years with demonstrated ownership of company-level programs, board and investor communication experience, and a track record of driving measurable business outcomes in a fast-scaling organization.