Pearl Talent - Chief of Staff

Pearl

1d • Remote

About The Position

Pearl Talent is seeking a Chief of Staff to act as a force multiplier for its founders as the company scales from a few million to $100M in revenue over the next three years. This role is designed to take on high-leverage, complex problems, including initiatives without a clear owner, cross-functional projects that require driving, and strategic questions needing thorough answers. The Chief of Staff will be expected to handle ambiguity and deliver clarity, decisions, and tangible outcomes. This position is explicitly designed as a track to VP of Operations, with the first year split between founder-directed special projects and taking ownership of Pearl's internal operating machine (processes, metrics, capacity planning). Within 12-18 months, the expectation is to formally lead the operations function.

Requirements

• Experience as a chief of staff at a fund or early-stage startup.
• Experience as an ex-consultant with subsequent years in a bizops or strategy role.
• Experience as a bizops or strategy and ops lead at a high-growth startup.
• Experience as an ex-IB or PE associate who transitioned into an operating role at a portfolio company.
• Experience as part of a founding team at an operationally intensive startup that scaled quickly.
• Experience in a services-based agency with leadership in operations/delivery.
• Desire to run operations, not just advise on them, with excitement for building the operational machine.
• Extreme ownership and speed; ability to close loops without being chased.
• A preference for building systems over heroics; ability to document, automate, or delegate.
• Structured thinking under ambiguity; ability to translate vague requests into scoped projects with timelines and owners.
• Strong writing and communication skills.
• Low ego and high standards; willingness to handle both strategic work and operational tasks.
• Comfort with a services business model; experience in staffing, recruiting, agencies, or other people-driven businesses is a plus, but not required. Pattern-matching from marketplaces or B2B SaaS is also acceptable.

Nice To Haves

• Experience in staffing, recruiting, agencies, or another people-driven business model.
• Pattern-matching from marketplaces or B2B SaaS.

Responsibilities

• Represent the founders in meetings, with the judgment to know when to decide and when to escalate.
• Run the operating rhythm, including leadership meetings, weekly and monthly business reviews, and quarterly planning.
• Drive initiatives that span across sales, client success, recruiting, and finance.
• Act as the connective tissue between founders and department leads, translating strategy into workstreams and surfacing critical information for leadership.
• Progressively take ownership of Pearl's internal operations, with the expectation of formally leading the function within 12-18 months.
• Build analyses for key strategic decisions such as pricing changes, new market entry, competitive positioning, and build-vs-buy evaluations.
• Stay informed about the market to identify best practices in staffing, recruiting, and services businesses.
• Take full ownership of high-priority initiatives from ambiguous mandate to shipped result, including launching new service lines, standing up new markets, fixing internal processes, or running diligence on partnerships/acquisitions.

Benefits

• Opportunity to build and grow quickly with significant leadership opportunities.
• Fully remote work environment.
• Unlimited PTO.
• Global retreats for team building.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed