Customer Retention Lead

FlagshipRTL•New York, NY

About The Position

As Customer Retention Lead, you’ll own the post-onboarding customer experience end-to-end: ensuring customers are successful, confident, and excited to renew and expand their use of Flagship. You’ll be the primary partner to our customers after go-live—helping them apply the product to real business decisions, navigating challenges as they arise, and translating feedback into meaningful product improvements. This is a highly cross-functional role at an early-stage startup. You’ll work closely with Product, Engineering, Data Science, and Sales, operate comfortably in ambiguity, and take real ownership over outcomes. We’re looking for someone who is deeply curious, outcome-oriented, and energized by helping customers solve hard problems. If you’ve lived in inventory spreadsheets, enjoy working directly with customers, and want to help shape both a product and a function from the ground up, this role is for you.

Requirements

5–10 years of inventory planning experience—you’ve owned OTBs, replenishment cycles, or assortment decisions at a brand or retailer
Familiarity with inventory planning or forecasting software (or strong intuition for how planners actually use tools)
A genuine desire to work directly with customers—you’ll be the face of Flagship for many accounts and a key driver of trust
Zero aversion to hands-on work—this is a strategic role, but as an early hire you’ll also be deep in the details
Strong triage skills—you can juggle 20+ accounts, quickly understand what customers are really asking, and get them unstuck
A pattern-recognizer mindset—you don’t just solve individual issues, you identify root causes and build scalable solutions
Builder mentality—you see gaps, inefficiencies, or missing processes and take initiative to fix them without being asked
Comfort operating independently with minimal direction—you prioritize, execute, and drive outcomes without waiting for a perfect roadmap
Clear, confident communicator—able to explain planning concepts to non-planners while also earning credibility with seasoned operators
Thrives in ambiguity and fast-paced environments—you stay calm, adaptable, and constructive when things change
This role has clear potential to grow into leading a broader CX function. We’re looking for someone who can scale with the company—shaping not just how we support customers today, but how we deliver world-class customer experience as we grow.

Nice To Haves

Experience working at a planning software
Experience working in a customer facing role
Worked previously at a ecommerce-focused appeal or accessories brand

Responsibilities

Act as the primary point of contact for a portfolio of customers post-onboarding, meeting with them regularly to support adoption, usage, and long-term success
Partner closely with customers to apply Flagship to real inventory and planning decisions
Own day-to-day customer support requests, triaging and resolving issues with speed, clarity, and empathy
Proactively educate customers on new features, product improvements, and best practices
Gather structured customer feedback and work closely with Product, Engineering, and Data Science to influence roadmap decisions
Design creative solutions and workarounds when customer needs extend beyond current product capabilities
Lead renewal and expansion conversations—ensuring customers clearly understand and experience the value we deliver
Monitor customer health and satisfaction, identifying risks early and taking action to mitigate them

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