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

2. Retention, Forecasting & Risk Leadership

• 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.

3. Coverage Model & Lifecycle Design

• 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 → Enablement → Optimization → Graduation) into lifecycle CSM ownership, including handoff brief quality, a ≥90% graduation rate, and <5% early churn.
• Peak Readiness: Lead merchant-facing peak planning (BFCM, Chinese New Year) with Operations: volume forecasts by merchant, inventory positioning, carrier mix, and surcharge communications delivered on a published calendar.

4. Value Realization & Merchant Outcomes

• Health Scoring on Leading Indicators: Partner with CS Operations to design and maintain a merchant health score built on volume trend, exception rate, SLA attainment, stockout risk, invoice disputes, and engagement, and use it to trigger plays rather than to describe history.
• Executive Business Reviews: Set the standard for MBRs/QBRs/EBRs that quantify merchant outcomes in the merchant's terms (cost per order, delivery speed by country, cash flow released, exception rate) and end with agreed priorities and owners.
• Voice of the Merchant Program: Own the merchant sentiment system: risk scoring as the primary operating signal, Customer Effort Score at the transaction level, and decision-maker NPS as the relationship instrument, each with a defined response path and owner.

5. Expansion via Services (Expand)

• Service Attach Rate: Own attach-rate targets and the expansion playbook for Portless services and partner solutions (Onward package protection, OpenBorder tax and duty compliance, Portless Capital inventory financing, US fulfillment expansion), with triggers, messaging, and objection handling documented for every play.
• Commercial Rigor: Coach CSMs on services-led discovery and business cases with clear merchant ROI. Partner with Sales on commercial terms and pipeline hygiene so influenced expansion is tracked in HubSpot, not in memory.
• Share-of-Wallet Growth: Identify merchants shipping a portion of their volume elsewhere and build the win-back and expansion motion with Sales and Operations.

6. Systems, Data & Cross-Functional Leadership

• HubSpot as System of Record: Set and enforce data standards (health, phase, renewal, and expansion fields) so forecasts and dashboards can be trusted without manual reconciliation.
• AI-Assisted CS Operations: Deploy AI tooling where it removes CSM toil (call summaries, business review prep, anomaly alerts on volume and exceptions, draft merchant communications) and set the quality bar for when a human must review before anything reaches a merchant.
• Product & Operations Feedback Loop: Convert recurring merchant friction into ranked, evidenced requests to Product and Operations, and close the loop back to merchants when changes ship.
• Cross-Functional Accountability: Partner with the Head of Technical Solutions on implementation handoffs, with Account Champions in the China and Chicago FCs on Tier 1 and Tier 2 execution, and with RevOps on CS Ops tooling and reporting.

Success Metrics (What "Good" Looks Like)

• Retention: Gross Revenue Retention at or above 90%, logo churn below 95%, and retention forecast accuracy within 10% points of actual.
• Growth: Net Revenue Retention above 100%, service attach rate of 15%, and influenced expansion pipeline and closed-won revenue tracked in HubSpot.
• Lifecycle: ≥90% Hypercare graduation rate, <5% early churn, and 100% of Enterprise and Strategic accounts with a current success plan and a business review in the last 90 days.
• Sentiment: Decision-maker NPS at or above 50 (in collaboration with all of Portless leadership), with every detractor contacted within 5 business days.
• Team: New CSMs carrying a full book within 90 days, voluntary CSM attrition below 10%, and a documented competency model with quarterly calibration.

Qualifications

• Fluent in English: Executive-level written and spoken communication. Able to run a board-ready retention review and a difficult merchant conversation in the same day.
• 8+ Years in Customer Success or Account Management: Including 3+ years directly managing CSMs or Account Managers with ownership of retention and expansion targets.
• Domain Expertise: Fulfillment, 3PL, cross-border logistics, or e-commerce operations experience is required. You understand SLA attainment, exception rates, carrier mix, inventory positioning, duties and de minimis exposure, and why merchants leave a 3PL.
• Modern CS Operating Model: Hands-on experience designing segmented coverage models, leading-indicator health scores, retention forecasting, digital and pooled CS motions, and outcome-based business reviews.
• Commercial Rigor: Track record of services-led expansion, attach-rate management, and forecasting NRR alongside GRR.
• Analytical Depth: Comfortable in HubSpot, a BI tool (Metabase or equivalent), and spreadsheets. SQL is a strong plus. You interrogate the data yourself before you ask an analyst.
• AI Fluency: Has deployed AI tooling in a CS team (call intelligence, drafting, anomaly detection) and can articulate where it helped, where it failed, and what guardrails it needed.
• Platform Familiarity: Shopify ecosystem knowledge, plus experience with Intercom, Jira, and Gong or similar call intelligence tools.

Values & Ways of Working

• Extreme Ownership: You own the retention number and every merchant escalation that reaches you, with a kind-and-caring orientation toward your team and the FC teams who execute.
• Judgment & Precision: Knows when to be strategically bold with a merchant's growth plan and when to be operationally precise about what Portless can deliver this week.
• Scalability: Builds playbooks, cadences, and coverage models that work for 100 merchants, and refuses one-off heroics as a growth strategy.

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 that a QBR slide about delivery speed means nothing if the carrier mix is wrong on Tuesday. You forecast churn with the discipline of a sales leader and coach with the patience of a great manager. You want to build the Customer Success Management function at a global 3PL from an early stage and be measured on Gross Revenue Retention, Net Revenue Retention, and the caliber of the team you build.