[Hiring] Director of Customer Success Management @Portless

Role Description

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 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.

Responsibilities

• Team Leadership & Talent
  • Build & Coach the Team: Hire, onboard, and develop CSMs & Hypercare managers across segments.
  • Capacity & Book Design: Set book-of-business size and revenue coverage per CSM by segment.
  • Performance Management: Define scorecards and hold the team to them with clear expectations.
• Retention, Forecasting & Risk Leadership
  • Own GRR and NRR: Deliver Gross and Net Revenue Retention for the merchant base.
  • Risk Register Cadence: Run the weekly at-risk review.
  • Churn Post-Mortems: Lead a written post-mortem within 10 business days of any logo loss.
  • Executive Escalations: Serve as the senior escalation point for Enterprise and Strategic merchants.
• Coverage Model & Lifecycle Design
  • Segmented Coverage: Design and run tiered engagement for Enterprise, Strategic, and Growth merchants.
  • Hypercare to CSM Graduation: Own the handoff standard from the four-phase Hypercare program.
  • Peak Readiness: Lead merchant-facing peak planning with Operations.
• Value Realization & Merchant Outcomes
  • Health Scoring on Leading Indicators: Partner with CS Operations to design and maintain a merchant health score.
  • Executive Business Reviews: Set the standard for MBRs/QBRs/EBRs that quantify merchant outcomes.
  • Voice of the Merchant Program: Own the merchant sentiment system.
• Expansion via Services (Expand)
  • Service Attach Rate: Own attach-rate targets and the expansion playbook for Portless services.
  • Commercial Rigor: Coach CSMs on services-led discovery and business cases.
  • Share-of-Wallet Growth: Identify merchants shipping a portion of their volume elsewhere.
• Systems, Data & Cross-Functional Leadership
  • HubSpot as System of Record: Set and enforce data standards.
  • AI-Assisted CS Operations: Deploy AI tooling where it removes CSM toil.
  • Product & Operations Feedback Loop: Convert recurring merchant friction into ranked requests.
  • Cross-Functional Accountability: Partner with various teams on implementation handoffs.

Success Metrics (What "Good" Looks Like)

• Retention: Gross Revenue Retention at or above 90%.
• Growth: Net Revenue Retention above 100%.
• Lifecycle: ≥90% Hypercare graduation rate.
• Sentiment: Decision-maker NPS at or above 50.
• Team: New CSMs carrying a full book within 90 days.

Qualifications

• Fluent in English: Executive-level written and spoken communication.
• 8+ Years in Customer Success or Account Management: Including 3+ years directly managing CSMs.
• Domain Expertise: Fulfillment, 3PL, cross-border logistics, or e-commerce operations experience.
• Modern CS Operating Model: Hands-on experience designing segmented coverage models.
• Commercial Rigor: Track record of services-led expansion and forecasting NRR alongside GRR.
• Analytical Depth: Comfortable in HubSpot, a BI tool, and spreadsheets.
• AI Fluency: Has deployed AI tooling in a CS team.
• Platform Familiarity: Shopify ecosystem knowledge, plus experience with Intercom, Jira, and Gong.

Values & Ways of Working

• Extreme Ownership: You own the retention number and every merchant escalation.
• Judgment & Precision: Knows when to be strategically bold and operationally precise.
• Scalability: Builds playbooks, cadences, and coverage models that work for 100 merchants.

Ideal Candidate Profile

You have led CSM teams through a retention turnaround or a scale-up and can show the before-and-after numbers. You have worked inside fulfillment or e-commerce and know the intricacies of delivery speed and carrier mix. You forecast churn with the discipline of a sales leader and coach with the patience of a great manager.