People Operations

We're hiring a People Operations Lead 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 $10M+ 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 60 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.

Hear why we exist, what we believe in, and who we’re building for: Watch here

Location: Fully Remote

Purpose of Your Role

You'll own the internal operating system that keeps Pearl running as we grow from a few million to $100M in revenue.

Right now, a lot of how Pearl runs internally still depends on the founders: onboarding new leaders, chasing end-of-week reports, preparing all hands, keeping sprints on track, and deciding which meetings are worth everyone's time. That works at 60 people. It won't work at 200. We need someone who takes all of that off our plates and does it better than we do.

This is an internal role. You'll build and run the systems that help every team at Pearl grow, get feedback, stay aligned, and execute: how people progress, how they're onboarded, how they give and receive feedback, how the company comes together at all hands, and how work moves week to week. You'll work directly with both founders and every department lead, and you'll be the person who makes sure the things we agree on actually happen.

Beyond running our operating systems, you'll be a force multiplier for the founders on the messy, high-leverage internal initiatives that don't have an owner yet. When we need something new stood up, like finding the right lawyers, choosing an accounting firm, or getting ahead of a compliance requirement, you take the ambiguous ask, figure out what good looks like, and own it until it's done.

There's a real opportunity to grow into a VP of Operations role. As Pearl scales toward $100M in ARR, the right person will expand from running our internal operating system to leading operations across the company, building and managing a team as the scope grows.

What You'll Own

1. Progression, Banding, Scorecards, and Reviews

• Build a clear progression banding system that works consistently across every org at Pearl, so everyone knows what the next level looks like and what it takes to get there.
• Organize our Scorecard system so it's simple enough that people actually do it, and so everyone receives feedback consistently.
• Connect banding, scorecards, and feedback into our 2x a year review and progression cycle, so promotions and growth conversations are consistent and fair across teams.
• Run the review cycle end to end: timelines, reminders, calibration, and follow-through.

2. Onboarding and Pearl Drivers Ed

• Standardize how new team members are onboarded across Pearl, including 30-60-90 day plans, first-week setup, and the check-ins that help new hires ramp quickly.
• Build and run Pearl Drivers Ed: the shared program that teaches every new hire how Pearl works, how we operate, and what great looks like here.
• Make sure new leaders, including new directors, have clear milestones and initiatives from day one.

3. All Hands

• Run our all hands from start to finish.
• Collate the data from across the company, decide who is speaking, and craft a story that connects what each team is doing to where Pearl is going.
• Keep all hands sharp, prepared, and worth everyone's time.

4. Operating Rhythm: End-of-Week Checks and Sprints

• Run end-of-week (EOW) checks with the different department leads, so reports come in on time and the founders can see what moved, what's stuck, and what needs attention.
• Help manage sprints across the company: set priorities, track progress, and make sure what we commit to gets done.
• Support our weekly and monthly data reviews, so leads are looking at the right numbers, both lagging indicators and trends.

5. Meeting Quality

• Own the question: are all the meetings happening across the company high value?
• Audit recurring meetings, cut or merge the ones that aren't earning their time, and make sure the rest have clear owners, agendas, and outcomes.
• Design formats that keep meetings engaging, such as rotating who leads and presents.

6. Founder Leverage

• Support the founders on the highest-leverage internal work wherever it's needed, including cleanup projects that don't yet have an owner.
• Clean up our internal processes and documentation on Notion and Docs, so the right information is easy to find and up to date.
• Act as the connective tissue between the founders and department leads, turning decisions into owners, timelines, and follow-through.

7. Founder-Directed Special Projects and New Initiatives

• Own the new initiatives the founders need stood up, end to end: scope the problem, research options, run the process, make a recommendation, and drive it to a decision and a working outcome.
• Examples include finding and onboarding the right legal counsel, selecting and transitioning to the right accounting firm, and leading compliance work as Pearl grows into new verticals and geographies. These are examples, not the full list: expect a steady stream of new, often ambiguous asks.
• Manage the outside partners these projects bring in (law firms, accountants, advisors, vendors), keeping them on scope, on timeline, and on budget.
• Once something is stood up, turn it into a repeatable process or hand it to a clear owner, so it doesn't fall back on the founders.

What Success Looks Like

Within your first 90 days, you've taken over the weekly operating rhythm from the founders. EOW reports come in on time from every lead, all hands runs through you, and every new hire goes through a standard onboarding with a clear 30-60-90 day plan.

Pearl has a progression banding system that every org uses, scorecards are being filled out and feedback is given consistently, and our first review and progression cycle has run on top of that system without the founders having to chase anyone. You've also taken several founder asks, such as standing up a new legal, accounting, or compliance workstream, from a one-line request to a finished outcome.

Within your first year, Pearl's internal operating system runs through you. Sprints stay on track, meetings across the company are fewer and better, and people know how they're growing and what it takes to get to the next level. When a new initiative needs to be stood up, the founders' first instinct is to hand it to you. The founders spend their time on the highest-value problems because they trust you to run everything else, and you're on a clear path to stepping into a VP of Operations role.

Requirements

What We're Looking For

• You might look like one of the following, and want a high-leverage role working directly with founders to build how a company runs:

• A chief of staff or business operations lead at a high-growth startup

• A people operations or internal operations lead who has built performance, onboarding, or review systems from scratch

• An ex-consultant who moved into an operating role and has owned real execution

• Someone on an early team at a fast-scaling, people-heavy company who ended up running the internal operating rhythm

• You've worked at a services business or agency and led internal operations

• You build systems people actually use. Anyone can design a process on paper. We want someone who has built scorecards, review cycles, or onboarding programs that people followed and that lasted after launch.

• You thrive on ambiguous founder asks. Give you a one-line request like "we need the right lawyers" or "figure out our compliance plan," and you come back with options, a recommendation, and then the finished outcome. You don't need a playbook to get started.

• Extreme ownership and follow-through. You close loops without being chased. When an EOW report is missing or a sprint slips, you notice first and fix it.

• You can lead without authority. You're comfortable holding department leads and directors accountable, and getting buy-in across teams who don't report to you.

• Strong storytelling and communication. You can take data from across the company and turn it into a clear story for all hands, a sharp update, or a document busy people actually read.

• High bar for everyone's time. You have opinions about what makes a meeting worth having, and you're willing to cut the ones that aren't.

• Low ego, high standards. You'll design a company-wide progression system on Monday and chase down a missing scorecard on Tuesday. Both matter, and you treat them that way.

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.