Lifecycle Marketer

What You'll Do

Churn & Retention

• Own the win-back and re-engagement strategy for lapsed free users and at-risk paid subscribers
• Diagnose the drivers of our current subscriber plateau using Stripe, PostHog, and CRM data, and build the first corrective campaigns within 30 days
• Design and ship lifecycle flows that recover users who abandon checkout which is currently our single largest funnel drop-off at roughly 80%
• Build a recurring churn cohort analysis and present findings to marketing and product leadership monthly

Trial & Conversion

• Own the trial-to-paid journey end to end including timing, messaging, and incentive structure for every touchpoint between sign-up and subscription
• Partner with Product Marketing to align in-platform messaging with lifecycle email and notification sequences
• Run structured A/B tests on trial length, onboarding sequencing, and conversion offers, and scale what works
• Build segmentation logic across our CRM contacts so every message reflects where a person actually is in their journey whether free, trial, lapsed, or paid

Email & CRM Strategy

• Set the strategic roadmap for all lifecycle and nurture email, partnering with the Marketing Operations Coordinator who owns execution and tooling
• Define the audience segments, triggers, and journey logic inside our CRM platform (Customer.io)
• Own subject line, send time, and frequency strategy across the lifecycle calendar, balancing conversion goals against list fatigue and unsubscribe risk
• Partner with Editorial on how The Batch and other newsletters feed into lifecycle journeys rather than existing as a disconnected channel

Measurement & Reporting

• Own lifecycle KPIs including free-to-paid conversion rate, checkout completion rate, 30/60/90-day retention, and churn rate. Report on them with a consistent cadence
• Build the LTV and cohort retention views our current dashboard is missing, partnering with Data Engineering on the underlying instrumentation
• Translate lifecycle performance into a clear narrative for leadership: what's improving, what isn't, and what you're doing about it

What You Bring

Required

• 3–6 years of experience in lifecycle, CRM, or retention marketing, with direct ownership of conversion or churn metrics
• Experience in subscription, edtech, or freemium-to-paid business models
• Hands-on experience with a marketing automation or CRM platform (Customer.io, Braze, Iterable, HubSpot, or similar)
• Demonstrated ability to read funnel and behavioral data (PostHog, Amplitude, Mixpanel, or similar) and translate it into a campaign strategy
• Experience designing and analyzing A/B tests with a clear hypothesis, control, and success metric
• Comfort working with subscription billing data (Stripe or similar) to understand the relationship between marketing activity and revenue
• Strong, clear writing, you will write or closely direct the copy for every lifecycle touchpoint
• A bias toward diagnosis before action, you investigate root cause before shipping a fix

Nice to Have

• Familiarity with the AI/ML or technical education landscape
• Experience partnering with engineering on event tracking and instrumentation
• Working knowledge of SQL for self-serve data exploration
• Experience with checkout or payment flow optimization specifically