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.