Senior Director, Retention Marketing - Remote AI-Driven

Nerdy; United States; Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Remote-first culture

401(k) match

Learning membership

AI tooling access

Job summary

Nerdy is seeking a Senior Director of Retention Marketing to lead email, messaging, and automated journeys for current and lapsed customers. You will own the end-to-end retention program and drive initiatives across activation, engagement, renewal, and winback using AI-native workflows.

This is a remote role based in the United States, reporting to executive leadership and partnering with Product, Sales, Customer Retention, and BI teams to maximize customer lifetime value and platform usage.

Qualifications

• Proven track record of retention marketing programs that measurably improve retention, reactivation, and customer lifetime value.
• Deep understanding of activation, product adoption, ongoing engagement, renewal, and winback.
• Exceptional customer judgment and product fluency; translate needs into messages and timing.
• Top 1% AI-native marketer: daily use of generative AI across the workflow including research, analysis, copy, landing pages, and automation.
• Strong copywriting and conversion rate optimization skills; write persuasively and optimize experiences.
• Strong quantitative fluency; define segments, lifecycle metrics, and experiment measurement.
• Impeccable written and verbal communication; align stakeholders and drive changes without direct authority.
• Highly organized, hands-on operator who thrives with ambiguity and ambiguity.
• Alignment with Nerdy’s apolitical, mission-focused culture.

Responsibilities

• Own retention marketing strategy and execution across onboarding, engagement, retention, renewal, winback, upsell, cross-sell, and referrals.
• Develop deep understanding of customers and products via research and collaboration with customer-facing teams.
• Build and improve retention programs across email, SMS, push, and web experiences; tailor reach and messaging.
• Personally create and launch communications, creatives, landing pages, and automated journeys using AI-native tools.
• Run continuous experimentation on messaging, offers, timing, targeting, and conversion experiences.
• Define customer data signals and reporting; guide data teams and translate insights into action.
• Partner with Product to shape features and experiences that support engagement and renewal.
• Align Sales and Customer Service on outreach and handoffs for a consistent customer experience.
• Build and maintain performance reports; iterate programs based on evidence.
• Continuously adopt and build AI tools and automations to scale impact.

Job description

Nerdy is seeking a Senior Director of Retention Marketing to lead email, messaging, and automated journeys for current and lapsed customers. You will own the end-to-end retention program and drive initiatives across activation, engagement, renewal, and winback using AI-native workflows.

This is a remote role based in the United States, reporting to executive leadership and partnering with Product, Sales, Customer Retention, and BI teams to maximize customer lifetime value and platform usage.