Customer Retention Lead

Flagship is building an innovative Sales and Operations Planning (S&OP) software that empowers DTC retail brands to maximize growth efficiency. Our platform seamlessly integrates with their first-party data to provide tailored insights based on advanced data analytics to drive cross-functional strategic decision-making.

At Flagship, we have built a multidisciplinary team of machine learning experts and industry professionals from the tech, commerce, and retail sectors. This has allowed us to build software that actually serves the needs of retail planning teams and executives and enables data-driven collaboration across departments. Our mission is to break businesses free from the limitations of outdated, siloed metrics and instead, focus on high-impact growth indicators that contribute to a positive net business outcome.

Join us in revolutionizing the way that retailers interact with their data to make more accurate, granular decisions informed by both their business expertise and machine learning algorithms.

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.

1. 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

2. Partner closely with customers to apply Flagship to real inventory and planning decisions 3. Own day-to-day customer support requests, triaging and resolving issues with speed, clarity, and empathy
4. Proactively educate customers on new features, product improvements, and best practices

5. Gather structured customer feedback and work closely with Product, Engineering, and Data Science to influence roadmap decisions

6. Design creative solutions and workarounds when customer needs extend beyond current product capabilities

7. Lead renewal and expansion conversations—ensuring customers clearly understand and experience the value we deliver

8. Monitor customer health and satisfaction, identifying risks early and taking action to mitigate them

● 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.

● Experience working at a planning software

● Experience working in a customer facing role

● Worked previously at a ecommerce-focused appeal or accessories brand

**This position is open only to US Residents with valid work authorization as visa/work sponsorship is not available at this time.