Chief of Staff - REMOTE - SR005

Department: Operations

Work Arrangement: Remote

Job Type: Independent Contractor, Full Time

Work Schedule: US Time Zone (candidate expected to be flexible with the client's preference)

Locations: Philippines, LATAM, South Africa, Kenya, and other remote regions with excellent English communication skills

About Pearl Talent

Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund. They're looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we've hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US.

Hear why we exist, what we believe in, and who we're building for: WATCH HERE

Why Work with Us?

At Pearl, we're not just another recruiting firm—we connect you with exceptional opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, be challenged, and build long-term, meaningful careers.

Role Overview

The Chief of Staff acts as the strategic and operational extension of executive leadership—bridging long-term priorities with day-to-day execution to ensure the organization runs efficiently and leadership focus stays on the highest-impact work. This role blends strategy, execution, and systems ownership, requiring someone who can move seamlessly between big-picture thinking and meticulous follow-through.

You will manage executive workflows, drive cross-functional initiatives, build and maintain internal systems, and ensure alignment across priorities, projects, and stakeholders. This role is ideal for highly autonomous operators who thrive in fast-paced environments, enjoy building structure from ambiguity, and take full ownership of outcomes.

Your Impact

Your work will significantly amplify executive effectiveness and organizational clarity. By managing priorities, systems, and execution rigor, you’ll reduce friction, prevent issues before they escalate, and ensure critical initiatives move forward without dropping details. Your operational discipline and strategic insight will enable leadership to operate at peak leverage while the organization scales sustainably.

Core Responsibilities

Strategic Partnership & Advisory — 25%

• Serve as a trusted advisor to executive leadership on priorities and decision-making
• Conduct research, analysis, and synthesis to inform strategic initiatives
• Translate strategic goals into actionable execution plans
• Track progress against key initiatives and flag risks or misalignment early
• Represent executive priorities in cross-functional discussions

Executive Support & Workflow Management — 25%

• Manage executive calendars with strategic prioritization
• Own inbox management, drafting and triaging communications as needed
• Prepare meeting agendas, briefs, and post-meeting action tracking
• Coordinate complex scheduling across stakeholders and time zones
• Track executive to-dos and ensure follow-through

Process, Systems & Documentation — 20%

• Design and maintain internal systems (CRM, project trackers, knowledge bases)
• Build and organize documentation, SOPs, and internal workflows
• Ensure data accuracy, consistency, and accessibility across tools
• Identify inefficiencies and implement lightweight process improvements
• Maintain clean information architecture and version control

Communication & Stakeholder Coordination — 15%

• Draft polished internal and external communications on behalf of leadership
• Coordinate stakeholder follow-ups and relationship touchpoints
• Track interactions and commitments across partners, clients, or investors
• Support preparation of reports, updates, and leadership materials
• Exercise strong judgment in managing sensitive communications

Project Management & Cross-Functional Execution — 10%

• Lead strategic projects from planning through execution
• Coordinate across teams to ensure alignment and accountability
• Track milestones, dependencies, and deliverables
• Remove blockers and escalate issues when needed
• Maintain visibility across all major initiatives

Operational Problem-Solving — 5%

• Proactively identify risks, gaps, and inefficiencies
• Troubleshoot operational issues before they escalate
• Coordinate vendors, tools, or service providers as needed
• Support light operational or financial tracking when required

Requirements

Must-Haves (Required)

Experience & Background

• 3–5+ years in Chief of Staff, Executive Assistant to C-level, Operations, Consulting, or similar roles
• Proven experience supporting senior leadership in fast-paced environments
• Strong track record managing complex, multi-step initiatives

Strategic & Operational Skills

• Strong analytical and problem-solving abilities
• Ability to think strategically while executing with precision
• Exceptional organization, prioritization, and follow-through

Communication & Professionalism

• Excellent written and verbal English communication
• High discretion and sound judgment with sensitive information
• Ability to interface confidently with senior stakeholders

Work Style

• Highly autonomous and proactive
• Comfortable building structure from ambiguity
• Proven success working fully remote

Nice-to-Haves (Preferred)

• 5+ years in Chief of Staff or senior operations roles
• Experience in startups, VC-backed companies, or high-growth environments
• Strategic consulting background
• Experience with investor relations, board materials, or fundraising support
• Multilingual capabilities (Spanish a plus)

Tools Proficiency

Must-Haves (Required)

• Google Workspace (Docs, Sheets, Drive, Calendar, Slides)
• Project & task management tools (Notion, Asana, ClickUp, Monday, or similar)
• CRM systems (platform-agnostic; must be comfortable configuring and maintaining)
• Spreadsheets for tracking, analysis, and reporting

Nice-to-Haves (Preferred)

• Notion (advanced workspace and documentation setup)
• CRM platforms (HubSpot, Salesforce, Airtable, Attio)
• Communication tools (Slack, Zoom, Microsoft Teams)
• AI tools (ChatGPT, Claude, Gemini) for drafting and research
• Loom or similar tools for documentation
• Scheduling automation tools (Calendly, Chili Piper)

Benefits

• Competitive Salary: Based on experience and skills
• Remote Work: Fully remote — work from anywhere
• Generous PTO: In accordance with company policy
• Direct Mentorship: Access to global industry leaders
• Learning & Development: Continuous growth resources
• Global Networking: Work with international teams
• Health Coverage (Philippines only): HMO after 3 months (full-time)

Our Recruitment Process

1. Application
2. Skills Assessment
3. Initial Screening
4. Top-grading Interview
5. Client Matching
6. Job Offer
7. Onboarding

Ready to Join Pearl Talent?

Build a long-term remote career supporting high-impact leaders and fast-growing companies. Join Pearl Talent and apply your strategic and operational strengths where they matter most.