Chief of Staff

Pearl Talent - Chief of Staff

We're hiring a Chief of Staff for Pearl, which finds exceptional talent from around the world, trains them to be AI-native, and places them into operational roles at startups as managed contractors: from client-facing roles to software engineers to executive assistants. We're 3x founders who’ve bootstrapped our company to a couple million in ARR and are adding six to seven figures in net new annualized revenue each month. Our clients span venture-backed tech and healthcare, including fast-growing startups and phenomenal US-based businesses that have raised over $3B in funding from Sequoia, a16z, Founders Fund, Y Combinator, and other top VC firms.

Today we're roughly 50 people managing a few hundred talents, growing fast and into new verticals. We started Pearl because we believe that even though opportunity isn’t created equal in the world, ambitious talent is. And our goal is to scale Pearl to $100M in ARR bootstrapped by placing 2777 operators into top startups in the next 3 years.

Location: USA remote

Purpose of Your Role

You'll be the force multiplier for both founders as we scale Pearl from a few million to $100M in revenue over the next three years.

This is not a calendar-and-inbox role. You'll take the highest-leverage, messiest problems off our plates: the initiatives that don't yet have an owner, the cross-functional projects that stall without someone driving them, and the strategic questions we haven't had time to properly answer. You'll be handed ambiguity and expected to return clarity, decisions, and shipped outcomes.

This role is explicitly designed as a track to VP of Operations. In year one, you'll split your time between founder-directed special projects and progressively taking ownership of Pearl's internal operating machine: our processes, metrics, and capacity planning. Within 12-18 months, the expectation is that you formally lead the operations function, having already proven you run it.

What You’ll Own

1. Founder Leverage
• Represent the founders in rooms they can't be in, with the judgment to know when to decide and when to escalate
• Run the operating rhythm: leadership meetings, weekly and monthly business reviews, quarterly planning, and follow-through on decisions made
2. Cross-Functional Execution
• Drive initiatives that cut across sales, client success, recruiting, and finance, where no single team owns the outcome
• Act as the connective tissue between the founders and department leads: translate strategy into workstreams, and surface what leadership needs to know before it becomes a fire
• Progressively take ownership of Pearl's internal operations, with the expectation of formally leading the function within 12-18 months
3. Strategic Analysis and Special Projects Ownership
• Build the analyses behind our biggest decisions: pricing changes, new market entry, competitive positioning, build-vs-buy calls
• Consistently keep up with the market and help us understand: what are the best staffing, recruiting, and services businesses doing that we're not?
• Take full ownership high priority initiatives as needed, from ambiguous mandate to shipped result (examples: launching a new service line, standing up a new market, fixing a broken internal process, running diligence on a partnership or acquisition)

What Success Looks Like

Within your first year, you own the operational day to day cadence of the business. The weekly and monthly operating rhythm runs through you: meetings have agendas, decisions have owners, and follow-through happens without founder chasing. You're the person who unblocks and coordinates VPs across the company, so cross-functional initiatives move without the founders having to broker them. The founders hand you problems and don't think about them again, and the VP of Operations seat is within reach because you're already doing the job.

What We're Looking For

• You might look like one of the following, and want a higher leverage role working directly with the CEO to launch strategic initiatives:
• A chief of staff at a fund or early stage startup
• An ex-consultant who then spent a few years in a bizops or strategy role
• A bizops or strategy and ops lead at a high-growth startup
• An ex-IB or PE associate who jumped into a portfolio company and has operating experience
• You were on the founding team at a operationally intensive startup that’s scaled quickly
• You’ve worked in an services based agency and led out operations/delivery
• You want to run operations, not just advise on them. This role ends in a VP of Operations seat. You should be excited by building the machine, not just working on projects adjacent to it.
• Extreme ownership and speed. You close loops without being chased. When something is yours, it's handled, and everyone around you knows it.
• Systems over heroics. You'd rather build the process that prevents the fire than be the person who's great at fighting it. You've documented, automated, or delegated yourself out of a job before.
• Structured thinking under ambiguity. You can take a vague one-line Slack message from a founder and turn it into a scoped project with a timeline, owners, and a definition of done.
• Strong writing and communication. Much of this role is turning fuzzy thinking into crisp documents, decision memos, and updates that busy people actually read.
• Low ego, high standards. You'll do strategy work on Monday and fix a broken spreadsheet on Tuesday. Both matter, and you treat them that way.
• Comfort with a services business. Experience in staffing, recruiting, agencies, or another people-driven business model is a plus, but not required. Pattern-matching from marketplaces or B2B SaaS works too.

Benefits

• Build and Grow Quickly - We’re scaling fast, and we trust that you’ll know best on the ground what needs to be done. You’ll have the opportunity to step into leadership early and own decisions that shape how our company grows.
• Fully Remote. Forever. - We’ve built Pearl with a multicultural DNA and teammates across 23 countries. We trust that the best work isn’t done behind a cubicle
• Unlimited PTO - We trust that you’ll get your work done, and we want to create space for you to take time away with the people you care about.
• Global Retreats - We create space for our teammates to get to know each other as people, rather than just to-do lists. We’ve shared meals, laughs, and sunrises across the world in places like Cancun, El Nido, Boracay, and Siargao**.**
• Ambitious and Kind Team - We build with the most competent people we know, and we maintain a low-ego, no-assholes policy. We’re looking for people who are sharp, kind, and open to being vulnerable when it matters.