Chief of Staff

JamaicaPosted Jul 16, 2026

Chief of Staff (Strategy & Operations) – Remote

Position Type: Full-Time, Remote
Working Hours: U.S. Business Hours

About the Role

At Pavago, one of our clients is hiring an experienced Chief of Staff to serve as a strategic partner to the CEO and executive leadership team. This is a high-impact leadership role focused on driving company strategy, improving operational execution, aligning cross-functional teams, and ensuring key initiatives move forward efficiently.

This is more than an operations role.

You’ll translate executive priorities into action, lead strategic initiatives, improve business processes, and provide leadership with the visibility needed to make informed decisions. Success in this role requires exceptional business judgment, operational excellence, and the ability to influence across teams without direct authority.

If you thrive in fast-paced, high-growth environments and enjoy balancing strategic thinking with hands-on execution, this role is a strong fit.

What You’ll Own

Strategic Planning & Execution

  • Partner with the CEO to define and execute company strategy.
  • Translate executive priorities into actionable plans and measurable outcomes.
  • Drive accountability across strategic initiatives and company-wide projects.
  • Identify execution risks and recommend proactive solutions.
  • Lead special projects and high-priority business initiatives.

Executive Partnership

  • Support the CEO with prioritization, planning, and decision-making.
  • Prepare executive briefings, presentations, reports, and communications.
  • Assist with board meetings, investor updates, and executive reporting.
  • Represent leadership in meetings and cross-functional initiatives when appropriate.
  • Handle confidential business matters with professionalism and discretion.

Cross-Functional Leadership

  • Align teams around company objectives and strategic priorities.
  • Facilitate communication and collaboration across departments.
  • Lead leadership meetings, follow-up processes, and action-item tracking.
  • Remove operational bottlenecks and improve execution.
  • Build strong relationships with internal and external stakeholders.

Operations & Business Performance

  • Improve internal processes, systems, and operating procedures.
  • Support quarterly planning, annual planning, and business reviews.
  • Develop executive dashboards and performance reporting.
  • Track KPIs, business metrics, and organizational performance.
  • Identify opportunities to improve efficiency, accountability, and scalability.

Communication & Organizational Alignment

  • Draft executive communications and company-wide updates.
  • Ensure consistent messaging across teams and stakeholders.
  • Support leadership communications related to strategic initiatives and partnerships.
  • Reinforce company culture, organizational alignment, and business priorities.

What Success Looks Like

  • Strategic initiatives are delivered on time and aligned with business goals.
  • Executive leadership operates with greater focus and efficiency.
  • Cross-functional teams remain aligned and accountable.
  • Business reporting provides clear visibility into performance.
  • Operational processes scale effectively alongside company growth.
  • Leadership has timely insight into priorities, risks, and execution.

What Makes You a Strong Fit

  • You think strategically while executing with urgency.
  • You solve problems before they become roadblocks.
  • You influence teams without relying on formal authority.
  • You communicate confidently with executives and stakeholders.
  • You remain organized while managing multiple high-priority initiatives.
  • You thrive in ambiguity and fast-changing environments.

Required Experience & Skills

Experience

  • 7+ years of experience in:
    • Chief of Staff
    • Strategy
    • Operations
    • Business Management
    • Consulting
    • Executive Leadership
  • Experience working directly with CEOs, founders, or executive leadership teams.
  • Proven success leading cross-functional initiatives and strategic projects.
  • Strong business acumen and operational decision-making skills.
  • Exceptional communication and stakeholder management abilities.
  • Strong organizational, analytical, and execution skills.
  • Ability to manage multiple priorities in fast-paced environments.

Nice to Have

  • MBA or other advanced degree.
  • Experience in:
    • High-growth startups
    • Technology companies
    • Consulting firms
    • Scaling organizations
  • Background in:
    • Management Consulting
    • Investment Banking
    • Corporate Strategy
    • Business Operations
  • Experience supporting board reporting and executive planning.
  • Experience leading organizational change and process improvement initiatives.

Tech Stack

  • Microsoft Office Suite
  • Google Workspace
  • Project Management Tools
    • Asana
    • Monday.com
    • Notion
    • Similar platforms
  • Executive dashboards and KPI reporting tools
  • CRM and business productivity platforms
  • AI productivity tools (ChatGPT, Microsoft Copilot, Claude, or similar)

What a Typical Day Looks Like

  • Meet with the CEO to review priorities and strategic initiatives.
  • Coordinate cross-functional projects and leadership action items.
  • Monitor KPIs and business performance dashboards.
  • Prepare executive presentations, reports, and communications.
  • Lead follow-ups on strategic initiatives across departments.
  • Remove execution bottlenecks and improve operational workflows.
  • Support leadership meetings, planning sessions, and business reviews.
  • Identify opportunities to improve organizational efficiency and scalability.

In short: You’ll serve as the CEO’s strategic partner, ensuring company priorities are executed effectively while aligning teams, improving operations, and driving organizational performance.

Key Metrics for Success (KPIs)

  • Strategic initiative completion rate.
  • Executive priority execution.
  • Cross-functional project delivery.
  • KPI reporting accuracy and visibility.
  • Operational efficiency improvements.
  • Stakeholder and leadership satisfaction.
  • Organizational alignment and accountability.

Why This Role Stands Out

  • Direct partnership with the CEO and executive leadership.
  • High ownership over strategy, operations, and company execution.
  • Significant influence on business growth and organizational performance.
  • Exposure to executive decision-making and company-wide initiatives.
  • Fully remote work environment.
  • Career progression into:
    • VP of Operations
    • Chief Operating Officer (COO)
    • General Manager
    • Executive Leadership

Interview Process

  1. Application Review
  2. Spark Hire Intro Video (3–5 minutes)
  3. Client Interview
  4. Offer & Onboarding

What Happens After You Apply

After submitting your application, you’ll receive an email invitation from Spark Hire to record a short 3–5 minute Intro Video. This is the first step in our hiring process and can be completed whenever it’s convenient for you.

Instead of multiple initial screening calls, you’ll have one opportunity to introduce yourself, discuss your experience supporting CEOs and executive leadership, and explain how you’ve led strategic initiatives, improved operations, aligned cross-functional teams, and driven organizational execution. You’ll also have the opportunity to highlight your leadership style, business judgment, and experience managing high-impact projects in fast-paced environments. Your video will be reviewed by the hiring team before moving to the client interview.

You can record your video as many times as you’d like before submitting it—only your final version will be reviewed.

Please keep an eye on both your inbox and spam folder for your Spark Hire invitation after applying.

Apply Now

If you’re passionate about strategy, operations, executive partnership, and driving meaningful business impact, we’d love to hear from you. Apply today and help shape the growth and execution of a high-performing organization.

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