Chief of Staff

This is a fully remote position, open to applicants in United States.

📋 Description

• Represent the founders in situations they cannot attend, determining when to act independently and when to escalate issues.

• Manage the operational rhythm, which includes leadership meetings, weekly and monthly business reviews, quarterly planning, and ensuring decisions are executed.

• Propel cross-functional initiatives across sales, client success, recruiting, and finance departments.

• Facilitate connections between the founders and department leaders by translating strategy into actionable workstreams and identifying potential risks.

• Gradually take ownership of Pearl’s internal operations, with the expectation of formal leadership of the function within the next 12 to 18 months.

• Develop analyses for pricing adjustments, new market entries, competitive positioning, and build-versus-buy assessments.

• Oversee staffing, recruiting, and service operations to pinpoint best practices.

• Lead high-priority initiatives from an ambiguous directive to a delivered outcome.

• Establish a structured operational routine, ensuring that meetings have agendas, decisions are assigned to owners, and follow-through is maintained.

• Remove obstacles and coordinate with VPs across the organization to ensure cross-functional initiatives move forward without the need for founder involvement.

⛳️ Requirements

• Proven experience as a chief of staff at a fund or early-stage startup, or as a former consultant with business operations/strategy expertise.

• Background as a business operations or strategy lead at a rapidly growing startup.

• Operational experience within a portfolio company following investment banking or private equity roles.

• Experience as part of a founding team at a startup that scaled rapidly and operationally intensive.

• Leadership experience in operations or delivery within a services-based agency.

• A strong desire to manage operations and advance into a VP of Operations position.

• Demonstrated extreme ownership and speed; capacity to close loops without needing reminders.

• Proficiency in building processes, automating tasks, delegating work, and minimizing dependence on individual heroics.

• Structured thinking in ambiguous situations; ability to transform vague requests into clearly defined projects with timelines, responsible parties, and criteria for completion.

• Exceptional writing and communication skills for preparing decision memos, documents, and updates.

• Low ego coupled with high standards; readiness to engage in both strategic and detailed operational tasks.

• Familiarity with a services business; experience in staffing, recruiting, agency work, people-driven businesses, marketplaces, or B2B SaaS is advantageous.

🏝️ Benefits

• Opportunity to assume leadership responsibilities early and make impactful decisions that influence company growth.

• Fully remote work arrangement.

• Unlimited paid time off (PTO).

• Participation in global retreats.

• A team environment that is both ambitious and supportive.

• A low-ego, no-asshole policy.