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.