Director (Head) of Customer Success Management

About Portless

Portless is a dynamic and innovative 3PL provider revolutionizing how businesses manage their direct supply chain. We help merchants deliver a fast, reliable post-purchase experience through fulfillment and logistics built for cross-border scale, powered by international warehouses and global orchestration so they can grow with confidence.

About the Role

As Director (Head) of Customer Success Management, you own the post-launch merchant relationship for every Portless merchant and the team that delivers it. You lead the Customer Success Management motions, including onboarding & lifecycle teams. You are the owner of Gross and Net Revenue Retention for the merchant base, and set the coverage model, playbooks, and cadences that turn the customer success flywheel (Adopt Realize Value Expand Renew with Confidence) into a repeatable system across the Enterprise, Strategic, and Growth segments.

This is a player-coach leadership role in a 0-to-1 environment. You will build the retention forecast leadership runs on, coach CSMs into commercially credible advisors, and partner with Technical Solutions, Operations, Product, Sales, and RevOps so that what we promise a merchant in a business review is what happens on the warehouse floor. You serve as an accountable partner in the success of our merchants and the Portless team members who support them.

What You'll Own (Responsibilities)

1. Team Leadership & Talent

• Build & Coach the Team: Hire, onboard, and develop CSMs & Hypercare managers (onboarding CSMs) across segments. Run weekly 1:1s, recorded call reviews (Gong), and a coaching cadence tied to a documented CSM competency model.
• Capacity & Book Design: Set book-of-business size and revenue coverage per CSM by segment, and re-balance books quarterly as merchants graduate from Hypercare or change tier.
• Performance Management: Define scorecards (retention, attach rate, health-score coverage, business review cade