Pearl Talent - Customer Success Manager

We're hiring a Customer Success Manager 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 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: Remote, working hours that overlap with our US-based clients.

Purpose of Your Role

You’ll own what happens after a client signs a proposal to work with Pearl. Every signed proposal is a founder or business owner trusting us with a critical seat on their team, and how fast that talent starts creating value decides whether the client pays, stays and grows with us. This role exists because our sales motion is adding new clients every month, and the path from signed proposal to paid, happy, expanding account needs a dedicated owner.

You’ll move three numbers:

→ Time to Value for new clients (30 days or less)

→ Conversion from Signed Proposal to Closed Won-Paid

→ Net revenue retention across your book through retention and seat expansion.

What You’ll Own

1. New Customer Onboarding
• Convert Signed Proposals into Closed Won-Paid deals by running a clear, fast path from signature to first invoice paid.
• Get every new client to value within 30 days: kickoff, role scoping, talent matching, first-week ramp and a check-in that confirms the placement is working.
• Coordinate recruiting, training and finance to provide a cohesive customer experience.
• Maintain a CSAT of 95% or higher and fix the steps that drag it down.
2. Account Retention and Expansion
• Manage a book of client accounts and own their retention, renewals and overall health.
• Act as a trusted advisor to each Customer Business Owner, learning their business well enough to make them see you as a value add business partner, and not as a vendor contact.
• Identify and close upsells, from additional seats to new role types, and bring in sales when a deal needs it.
• Catch risk early by tracking talent performance and client sentiment, and step in before a small issue becomes a cancellation.
3. Customer Experience Process and Insights
• Turn what works in onboarding and expansion into repeatable playbooks and processes so we can increase onboarding velocity while maintaining our high quality bar.
• Bring what customers tell you back to the founders, sales and recruiting so it shapes how we hire, train and sell.

What Success Looks Like

In your first 90 days, you’ve taken over your assigned book of accounts, met every Customer Business Owner, and personally run onboarding for new assigned Customers from signed proposal to paying customer. Every Customer you onboard sees value from talent in 30 days, and you’ve written down the onboarding steps that worked and the ones that didn’t.

By six months, onboarding runs on a playbook you built. New clients hit value in 30 days or less at 95% CSAT or higher, nearly every signed proposal converts to Closed Won-Paid, and you’ve closed your first upsells from your book.

By twelve months, your book is growing on its own. Net revenue retention is above 100% because expansion outpaces churn, at-risk accounts are flagged and saved before they cancel, and the founders trust you with our most important client relationships.

What We're Looking For

• You might look like one of the following, and want to own the full client relationship at a company that is growing every month:
• A Customer Success Manager at an early stage, high-growth SaaS, healthcare technology or fintech company who owned a book end to end
• An onboarding or implementation lead who got customers live fast and then moved into managing and expanding accounts
• An account manager at a services or staffing business who kept clients and grew them into larger accounts
• You have owned retention at an early stage, high-growth company:
• The number was yours, you can tell us what it was when you started and what it was when you left, and you can name the accounts you saved.
• You have onboarded new customers in 30 days or less at 95% CSAT or higher:
• You can walk us through the steps you ran and where customers usually got stuck.
• You have identified and closed upsells yourself. You see expansion as part of the job and you’re comfortable asking a client for more business when it’s right for them.
• You build trust with founders and business owners quickly. They come to you for advice on their team and their business, not only when something breaks.
• You close loops without being chased. When a client is waiting on something from you, it’s handled, and the people around you know it.
• You write clearly and keep good records in the CRM. Your accounts are documented well enough that someone else could pick them up tomorrow.
• You have worked in Software as a Service, Healthcare Technology or Financial Technology. Experience in a venture-backed startup is a plus, and familiarity with healthcare technology is a strong plus since healthcare is our first vertical.

• 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.