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.

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.

• 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 cadence) and hold the team to them with clear expectations and clear support.

• Own GRR and NRR:
  Deliver Gross and Net Revenue Retention for the merchant base and publish a monthly retention forecast with named at-risk accounts, dollar exposure, and save plans.
• Risk Register Cadence:
  Run the weekly at-risk review. Every Yellow or Red account has a root cause, an owner, a dated next step, and an executive sponsor where needed.
• Churn Post-Mortems:
  Lead a written post-mortem within 10 business days of any logo loss or volume loss in the Enterprise and Strategic segments, and convert findings into playbook, operations, or product changes.
• Executive Escalations:
  Serve as the senior escalation point for Enterprise and Strategic merchants, driving root cause and corrective action across Operations, Technical Solutions, and Engineering.

• Segmented Coverage:
  Design and run tiered engagement for Enterprise, Strategic, and Growth merchants, including a digital and pooled motion for the long tail so high-touch time goes where revenue and risk concentrate.
• Hypercare to CSM Graduation:
  Own the handoff standard from the four-phase Hypercare program (Stabilization to Enablement to Optimization to Graduation) into lifecycle CSM ownership, including handoff brief quality, a ≥90% graduation rate, and