Head of Customer Experience & Retention

Head of Customer Experience & Retention

Location: Oakland, CA (Hybrid preferred)

Compensation: $150,000 - $175,000

Reports to: CEO

Type: Full-time, Senior Leadership

Stage: High-growth, premium DTC + Subscription brand, Startup

If you are customer obsessed, believe in a clean, healthy, and transparent food system free from synthetic chemicals and pesticides, and want to make a positive change in the global food system, this role is for you.

Heirloom Coffee Roasters is building one of the most intentional retention systems in the clean, healthy food category designed around Access, Value, and Experience.

We are hiring a Head of Customer Experience & Retention to own and execute this strategy end-to-end.

This role is accountable for turning first-time buyers into lifelong subscribers, building emotional loyalty to the mission through education and access, and increasing customer lifetime value while protecting Heirloom’s premium brand.

The Head of Retention & Customer Experience is the owner of customer lifetime value and will:

• Improve 90-day repurchase rate from ~10% → 45% within 12 months
• Expand subscription conversion, tenure, and contribution margin
• Design, build and scale Heirloom’s loyalty ecosystem
• Reduce churn through experience, mission, and loyalty
• Turn customers into loyalists, advocates, and evangelists

1. Retention Strategy & Execution

• Own Heirloom’s Retention Operating System across lifecycle stages:
• First-time buyer
• Second purchase conversion
• Active subscriber
• Power user
• At-risk / lapsed
• Translate the Access, Value, Experience framework into daily execution
• Build, maintain, and evolve:
• Lifecycle email and SMS flows
• Subscription onboarding and save flows
• Loyalty and milestone programs
• Win-back and reactivation strategies
• Ensure all programs reinforce Heirloom’s premium, clean & healthy, culinary positioning

• Own subscription strategy and performance:
• Attach rate
• Tenure
• Monthly churn
• Subscriber LTV
• Lead the rollout and optimization of Heirloom’s loyalty program
• Design milestone rewards that feel earned, emotional, and brand elevating
• Partner with Operations to ensure flawless fulfillment of rewards and experiences

• Own the end-to-end customer experience across all DTC touchpoints
• Set CX standards, tone, and escalation paths
• Turn customer support into a retention engine
• Build & implement churn-prevention systems before customers reach cancellation with our agency partners

• Own all retention KPIs and reporting
• Build and manage cohort-based analysis by:
• Acquisition channel
• Product
• Subscription vs one-time
• Tenure
• Maintain an executive-ready retention dashboard with weekly visibility
• Run weekly retention business reviews with leadership

• Partner with:
• Founder
• Roaster team/ Q-Grader
• Content team
• Execute subscriber-only experiences including:
• Quarterly audio notes
• Digital cuppings
• Early access programs
• Office hours and private events
• Ensure all content educates, deepens trust, and builds intimacy

• Manage
• CRM / Lifecycle Agency
• Content Manager
• Loyalty vendors and platforms
• Own tooling decisions (CRM, loyalty, subscription CX stack)
• Scale systems that work

• 90-day repurchase rate reaches or exceeds 45% within 8 months
• Subscription becomes the dominant purchase path for repeat customers
• Subscriber churn consistently under 3.5% monthly
• Loyalty program shows meaningful lift in repeat purchase and tenure
• Customers actively reference Heirloom’s story, standards, clean & healthy attributes, and access as reasons they stay.
• Turn customers into loyalists & evangelists

Required Experience

• 6+ years in customer experience & retention, lifecycle marketing, or customer experience
• Deep experience in:
• DTC ecommerce
• Subscriptions
• Loyalty programs
• Strong analytical background with comfort in dashboards, cohorts, and experimentation
• Experience owning revenue-impacting KPIs
• Hands-on operator who can both strategize and execute
• Ability to work in a small and agile team

Strongly Preferred

• Experience in premium CPG, food &…