Chief of Staff
Remote
Full-Time
US-Aligned
7+ Years
Apply Now
Role Overview

As a Chief of Staff at Tailored Teams, you will operate as a strategic extension of a founder or senior executive, helping translate vision into execution across the organization. This is a high-impact leadership role designed for experienced operators who thrive in ambiguity, ownership, and cross-functional influence.

You’ll work closely with executive leadership to drive alignment, prioritize initiatives, and ensure that critical decisions turn into measurable outcomes. The role sits at the intersection of strategy, operations, and communication — requiring strong judgment, discretion, and the ability to move seamlessly between big-picture thinking and hands-on execution.

This position is ideal for professionals who want deep exposure to leadership decision-making, increasing scope over time, and a clear path toward expanded executive responsibility.

Key responsibilities
  • Act as a strategic thought partner to the founder or executive leadership
  • Translate executive priorities into clear plans, timelines, and execution frameworks
  • Drive alignment across teams, ensuring initiatives move forward efficiently
  • Manage cross-functional projects and high-priority initiatives from start to finish
  • Prepare executive-level briefs, updates, presentations, and decision summaries
  • Identify risks, blockers, and misalignment early and proactively resolve them
  • Support operational cadence through planning, reviews, and follow-ups
  • Serve as a trusted point of contact between leadership and internal stakeholders
  • Maintain discretion and confidentiality across sensitive discussions and decisions
What We’re Looking For
  • Minimum 7+ years experience working closely with founders, C-suite executives, or senior leadership
  • Background in operations, strategy, consulting, or senior executive support
  • Proven ability to operate in fast-paced, high-accountability environments
  • Strong strategic thinking combined with hands-on execution ability
  • Exceptional written and verbal English communication skills
  • High emotional intelligence and stakeholder management capability
  • Ability to work autonomously with minimal direction
  • Comfort navigating ambiguity, shifting priorities, and incomplete information
  • Full-time commitment with no conflicting engagements
What success looks like
  • You are fully trusted to manage executive priorities and drive initiatives without micromanagement
  • Leadership relies on you for clarity, judgment, and structured decision-making
  • Strategic initiatives move faster and with less friction because of your involvement
  • Teams are aligned around priorities, timelines, and ownership
  • Risks and misalignment are surfaced early and resolved proactively
  • You reduce cognitive load for executives by bringing structure to complex situations
  • By 12 months, your impact is felt across the organization through stronger execution and alignment
Tools & Ways of Working
  • Google Workspace (Docs, Sheets, Slides, Calendar)
  • Slack for async and real-time communication
  • Notion or similar tools for documentation, planning, and knowledge management
  • Project and task management tools as required
  • AI tools for research, summarization, and productivity

You should be comfortable learning new tools quickly and improving systems independently.

Why This Role Is Different
  • Long-term executive leadership placements, not short-term consulting or gigs
  • High trust and autonomy from day one
  • Direct exposure to founder-level decision-making
  • No micromanagement or task-ticket culture
  • Designed for experienced operators, not junior support roles
growth & career path
  • Expand into broader executive leadership or operating roles over time
  • Increased ownership across strategy, operations, and execution
  • Deep exposure to leadership decision-making and company building
  • Long-term partnership and ongoing support from the Tailored Teams leadership team

This role is built for professionals seeking sustained growth, not a temporary title.

What You Get
  • Long-term, stable engagement
  • Real ownership and trust
  • Competitive compensation (experience & location based)
  • A career path, not just a role
Hiring process
  • Application review
  • Screening interview
  • Scenario-based assessment
  • Founder match interview
  • Placement & onboarding