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Nerdy

Senior Director – Retention Marketing

Nerdy

. Own retention marketing strategy and execution across onboarding, engagement, retention, renewal, winback, upsell, cross-sell, and referrals .

Posted 10/16/2026full-timeRemote • United StatesSeniorWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in retention marketing strategy and execution, leveraging AI-native tools for customer engagement and communication. Proven ability to analyze customer behavior and data to drive measurable improvements in retention and customer lifetime value.

Highest-signal resume keywords
Retention Marketing StrategyCustomer Behavior AnalysisAI-Native Tools ProficiencyCopywriting and Conversion Rate OptimizationQuantitative Fluency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
Retention Marketing ProgramsCustomer ResearchBehavioral AnalysisCustomer SegmentationExperiment MeasurementLifecycle MetricsCampaign DevelopmentData Usability ValidationCustomer Lifetime Value ImprovementSubscription Retention Mechanics
Soft Skills
Exceptional Customer JudgmentImpeccable Written CommunicationStrong Verbal CommunicationHighly OrganizedHands-On Operator
Tools & Technologies
AI-Native Builder ToolsCursorClaude CodeCodexVercelNetlifySupabase
Industry Keywords
Customer EngagementRenewalWinbackUpsellCross-SellCustomer FrictionCustomer ExperienceOperational ChangesPerformance ReportingMission-Focused Culture

About the role

Key responsibilities & impact
  • Own retention marketing strategy and execution across onboarding, engagement, retention, renewal, winback, upsell, cross-sell, and referrals
  • Develop deep understanding of customers and products through customer research, behavioral analysis, and partnership with customer-facing teams
  • Identify customer friction, missed value, and reasons to take the next step
  • Build and improve retention marketing programs across email, SMS, push notifications, and web experiences
  • Determine audiences, timing, and messaging based on customer needs, behavior, and relationship stage
  • Personally create and launch customer communications, creative, landing pages, and automated journeys using AI-native tools
  • Run continuous experimentation on messaging, offers, timing, targeting, and conversion experiences
  • Measure incremental impact on customer behavior and business results using appropriate controls
  • Define customer data, behavioral signals, and reporting requirements
  • Direct data-team priorities and requirements, validate data usability, and turn findings into action
  • Partner with Product to shape features and customer experiences supporting engagement, retention, and reactivation
  • Align Sales and Customer Service on outreach, offers, handoffs, and operational changes
  • Communicate clearly and drive consistent implementation across marketing and human interactions
  • Build and maintain performance reporting and communicate results and priorities to leadership
  • Continuously adopt and build AI tools and automations to increase retention-marketing speed, quality, and scale

Requirements

What you’ll need
  • Proven track record of personally building and scaling retention marketing programs that measurably improve retention, reactivation, and customer lifetime value
  • Deep understanding of subscription retention mechanics, including activation, product adoption, ongoing engagement, renewal, and winback
  • Experience translating software capabilities and customer behavior into effective marketing programs; consumer subscription experience is a plus
  • Exceptional customer judgment and product fluency
  • Daily, fluent use of generative AI across customer research, audience and insight analysis, copy and creative development, landing page creation, experimentation, and automation
  • Ability to point to real campaigns, pages, and tools built through AI-assisted workflows
  • Working proficiency with AI-native builder tools such as Cursor, Claude Code, Codex, Vercel, Netlify, and Supabase
  • Strong copywriting and conversion rate optimization skills
  • Strong quantitative fluency and experience defining customer segments, lifecycle metrics, and experiment measurement
  • Ability to analyze results and translate customer-data gaps into actionable requirements for data and engineering teams
  • Impeccable written and verbal communication
  • Highly organized, hands-on operator who thrives with ambiguity and minimal support
  • Alignment with Nerdy’s apolitical, mission-focused culture

Benefits

Comp & perks
  • Competitive compensation
  • Clear promotion pathways
  • Equity (RSUs)
  • 401(k) plan with company match and immediate vesting
  • Remote-first culture with flexibility across time zones and working styles
  • Flexible time off
  • All-inclusive learning membership for the employee and household, including 1:1 tutoring hours, unlimited on-demand classes, and the full suite of learning products and services
  • Access to cutting-edge AI tools
  • Medical, dental, vision, life, short-term disability, and long-term disability plans
  • Maternity, paternity, and adoption leaves