Churn & Retention
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Own the win-back and re-engagement strategy for lapsed free users and at-risk paid subscribers
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Diagnose the drivers of our current subscriber plateau using Stripe, PostHog, and CRM data, and build the first corrective campaigns within 30 days
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Design and ship lifecycle flows that recover users who abandon checkout which is currently our single largest funnel drop-off at roughly 80%
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Build a recurring churn cohort analysis and present findings to marketing and product leadership monthly
Trial & Conversion
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Own the trial-to-paid journey end to end including timing, messaging, and incentive structure for every touchpoint between sign-up and subscription
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Partner with Product Marketing to align in-platform messaging with lifecycle email and notification sequences
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Run structured A/B tests on trial length, onboarding sequencing, and conversion offers, and scale what works
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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
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Set the strategic roadmap for all lifecycle and nurture email, partnering with the Marketing Operations Coordinator who owns execution and tooling
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Define the audience segments, triggers, and journey logic inside our CRM platform (Customer.io)
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Own subject line, send time, and frequency strategy across the lifecycle calendar, balancing conversion goals against list fatigue and unsubscribe risk
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Partner with Editorial on how The Batch and other newsletters feed into lifecycle journeys rather than existing as a disconnected channel
Measurement & Reporting
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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
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Build the LTV and cohort retention views our current dashboard is missing, partnering with Data Engineering on the underlying instrumentation
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Translate lifecycle performance into a clear narrative for leadership: what's improving, what isn't, and what you're doing about it
Required
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3–6 years of experience in lifecycle, CRM, or retention marketing, with direct ownership of conversion or churn metrics,
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Experience in subscription, edtech, or freemium-to-paid business models
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Hands-on experience with a marketing automation or CRM platform (Customer.io, Braze, Iterable, HubSpot, or similar)
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Demonstrated ability to read funnel and behavioral data (PostHog, Amplitude, Mixpanel, or similar) and translate it into a campaign strategy
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Experience designing and analyzing A/B tests with a clear hypothesis, control, and success metric
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Comfort working with subscription billing data (Stripe or similar) to understand the relationship between marketing activity and revenue
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Strong, clear writing, you will write or closely direct the copy for every lifecycle touchpoint
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A bias toward diagnosis before action, you investigate root cause before shipping a fix
Nice to Have
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Familiarity with the AI/ML or technical education landscape
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Experience partnering with engineering on event tracking and instrumentation
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Working knowledge of SQL for self-serve data exploration
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Experience with checkout or payment flow optimization specifically
In your first 30 days, you will have audited the current lifecycle and CRM setup, diagnosed the leading drivers behind our checkout abandonment and subscriber plateau, and identified the two or three highest-leverage fixes. Within 30 days, you will have shipped your first churn and win-back campaigns, established a recurring reporting cadence, and have early data showing directional improvement in free-to-paid conversion. In 6 months, you will have measurably improved retention and conversion, built a durable lifecycle infrastructure with the Marketing Engineer and Marketing Operations Coordinator, and become the team's authority on what drives a user from sign-up to loyal subscriber.