Chief of Staff

This is a fully remote position, open to applicants in United States, +2 more locations.

📋 Description

• Collaborate with the founder to convert priorities, initiatives, and strategic vision into structured plans with designated owners, timelines, and success metrics.

• Manage special projects and organizational initiatives at the founder level from initial scoping to delivery and performance measurement.

• Ensure accountability across the founder's priorities while identifying conflicts, dependencies, and risks.

• Create strategy briefs, decision memos, board materials, and organizational roadmaps.

• Act as a strategic thought partner to the founder.

• Develop and enhance hiring infrastructure, resource allocation processes, capacity planning, and systems for cross-functional coordination.

• Design hiring systems that include interview frameworks, candidate evaluation rubrics, and onboarding procedures.

• Oversee organizational resource allocation and capacity planning.

• Establish regular leadership meeting schedules, decision-making frameworks, communication protocols, and reporting structures.

• Identify operational bottlenecks and implement effective solutions.

• Manage complex cross-functional initiatives.

• Coordinate and troubleshoot issues across various departments.

• Represent the founder's office in internal discussions.

• Foster working relationships throughout the organization.

• Ensure clear internal communication regarding strategy, priorities, and decisions.

• Prepare the founder for meetings, presentations, and decision-making processes.

• Monitor organizational health metrics and key initiatives.

• Potentially lead AI transformation projects, manage client CEOs, drive sales initiatives, support recruiting efforts, oversee client delivery, enhance client data and analytics value, and spearhead client go-to-market initiatives.

⛳️ Requirements

• 5-7+ years of experience in high-performing environments such as Chief of Staff roles, strategic operations, management consulting, venture capital/private equity, business development, or startup leadership positions.

• AI-native, possessing experience in tinkering, building small tools, automating workflows, and sharing insights.

• Proven track record of completing ambiguous and complex initiatives successfully.

• Strong systems thinking and process design capabilities.

• Exceptional project management and coordination skills across multiple concurrent work streams.

• High proficiency in Google Workspace, Asana/Notion, and Slack.

• Intermediate to advanced comfort level with AI-powered productivity tools.

• Excellent written and verbal communication skills.

• Bachelor’s degree or equivalent experience.

• Commitment to ethical practices and responsible business operations.

• Preference for working hours that overlap with EST.

• An advanced degree in a relevant field is a plus.

• Availability for occasional travel of 10–25%.

• Bonus experience in high-growth startups, venture studios, AI/tech companies, talent operations, organizational design, B2B business development, or board-level strategy and operations.

🏝️ Benefits

• Remote-friendly work arrangement.

• Occasional travel (10–25%) for company offsites, key events, and leadership meetings.

• Full-Time position for US Applicants.

• Independent Contractor role for Canadian Applicants.