Sr Manager, Customer Success

CargoSprint

1h•Remote

About The Position

CargoSprint is building a new Customer Success function and is looking for a leader to build it. As Senior Manager, Customer Success, you will own the post-sale customer lifecycle for CargoSprint's growing portfolio of logistics technology products: payments, appointments, and visibility. This is a greenfield role with executive backing and a clear mandate: ensure that every customer who signs with CargoSprint activates, adopts, and grows.

Requirements

5+ years in Customer Success, account management, or a post-sale customer-facing role at a SaaS, logistics technology, fintech, or B2B platform company.
Demonstrated ability to design and operate a structured CS playbook across onboarding, adoption, retention, and expansion—with measurable outcomes.
Hands-on experience tracking and reporting CS KPIs including Time to Value, NRR, GRR, Customer Health Score, Churn Rate, and NPS. You know what these metrics mean and how to move them.
Proven track record owning and presenting weekly and monthly business reviews to senior leadership, with the ability to translate lifecycle complexity into clear, actionable narrative.
Experience managing a tiered book of business—High-Touch, Mid-Touch, and Low-Touch—with appropriate playbooks and resource allocation for each segment.
Ability to work across Product, Support, Sales, and Account Management to align the CS function with the broader customer experience and revenue agenda.
Comfort with CS platforms and CRM tooling (Salesforce, HubSpot, Gainsight, or equivalent) and the analytical rigor to build dashboards and track customer health at scale.

Nice To Haves

Background in logistics, freight forwarding, payments, or port and terminal technology is a strong differentiator. Our customers—freight forwarders, truckers, and facility operators—operate in a complex, high-stakes environment, and pattern recognition matters.
Experience standing up a Customer Success function from scratch, including defining the playbook, instrumentation, segmentation model, and metrics framework.
Experience building and maintaining customer-facing knowledge centers (Confluence, Guru, Zendesk Guide, or equivalent) that serve both self-service and agent enablement goals.
Familiarity with designing automated onboarding flows, triggered email sequences, and in-app engagement tools for low-touch customer segments.
Exposure to Lean, Six Sigma, or similar operational frameworks for identifying and eliminating systematic causes of customer failure to activate or retain.

Responsibilities

Design and operate a structured, repeatable playbook that moves customers from contract signature to measurable value—before issues arise, before churn sets in, and before Support has to intervene.
Own onboarding, health monitoring, retention, and expansion signals across a tiered book of business that spans major freight forwarders, regional drayage companies, and individual owner-operators.
Bring data discipline to every layer of the function, tracking Time to Value, Customer Health Score, Net Revenue Retention, and Churn Rate on a weekly and monthly basis—and presenting those metrics clearly to executive leadership.
Design and own a defined onboarding journey for new customers, including how-to resources, training sessions, and milestone check-ins within the first 30 to 60 days of engagement.
Own Time to Value (TTV)—the speed at which a new customer completes their first successful transaction on the CargoSprint platform. This is the primary activation metric for the function.
Build and continuously improve onboarding playbooks tailored to 2 to 3 key product and customer segment combinations, starting with CargoSprint's highest-volume use cases.
Monitor product usage signals—login frequency, transaction volume, feature adoption—to identify customers who are disengaging before they churn or escalate to Support.
Build and maintain a Customer Health Score for each account, using usage data, support ticket rates, and NPS inputs. Trigger proactive outreach when scores fall below defined thresholds.
Establish baseline health score definitions and the data instrumentation required to make them operational—one of the function's three founding priorities.
Intervene proactively when usage declines, a renewal approaches, or a new product feature is directly relevant to a customer's workflow—before Account Management has to chase.
Identify natural expansion opportunities and route them to Account Management with full context. Customer Success identifies the signal; AM closes the revenue.
Drive Net Revenue Retention (NRR) above 100% by ensuring existing customers are growing their usage and spend without requiring reactive intervention.
Manage a segmented book of business across three engagement tiers: High-Touch (named CSM coverage for enterprise accounts), Mid-Touch (pooled team with structured onboarding for commercial accounts), and Low-Touch (automated flows and self-serve for SMB and long-tail payees).
Allocate CS resources based on customer size and strategic value, ensuring the highest-value accounts receive proportional attention without under-serving the long tail.
Design and maintain automated onboarding flows and triggered email sequences for low-touch segments, reducing cost-to-serve without sacrificing activation quality.
Define, instrument, and own the core CS metrics: Time to Value, Net Revenue Retention, Gross Revenue Retention, Customer Health Score, Churn Rate, Product Adoption Rate, NPS, and Expansion Revenue.
Build and present Weekly Business Reviews (WBR) and Monthly Business Reviews (MBR) to executive leadership with clear narrative analysis of lifecycle trends, at-risk accounts, and initiative status.
Identify the top five reasons new customers fail to activate within 30 days—a founding workstream for the function—and translate findings into playbook improvements and Product feedback.
Own the customer-facing knowledge center: how-to articles, FAQs, and product guides that reduce inbound Support volume and enable customers to help themselves.
Provide structured Voice of Customer input to Product Management, translating recurring customer friction points and feature requests into actionable roadmap influence.
Coordinate tightly with the VP of Customer Support & Operations to ensure that Support's reactive ticket data informs CS's proactive outreach priorities—and vice versa.