Flagship · 3 days ago
Customer Retention Lead
United States
Full-time
Remote
Senior Level
5+ years expFlagship is building innovative Sales and Operations Planning software for DTC retail brands. The Customer Retention Lead will own the post-onboarding customer experience and ensure clients are successful and satisfied with the product, working cross-functionally with various teams to drive customer engagement and product improvements.
Artificial Intelligence (AI)Machine LearningRetail TechnologySaaS
No H1B
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
Qualification
Required
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
Preferred
Experience working at a planning software
Experience working in a customer facing role
Worked previously at a ecommerce-focused appeal or accessories brand
Company
Flagship
Flagship develops a SaaS data science solution that brings predictive machine-learning intelligence to retail.
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$12.92MKey Investors
Insight Partners
2023-07-11Seed· $5M
2023-06-08Seed· $7.92M
Leadership Team
Justin Abrams
Co-Founder & CEO
Haftan Eckholdt
Chief Technology Officer
Recent News
Sydney Morning Herald - Business
2025-11-04
Sydney Morning Herald - Business
2025-09-12
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