Senior Director – Retention Marketing

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of the retention marketing strategy and its execution, focusing on onboarding, engagement, retention, renewal, winback, upselling, cross-selling, and referrals.

• Cultivate a comprehensive understanding of customers and products through customer research, behavioral analysis, and collaboration with customer-facing teams.

• Identify areas of customer friction, missed opportunities, and motivators for progression.

• Design and enhance retention marketing programs utilizing email, SMS, push notifications, and web experiences.

• Determine target audiences, timing, and messaging tailored to customer needs, behaviors, and stages of relationship.

• Personally create and implement customer communications, creative content, landing pages, and automated journeys using AI-native tools.

• Conduct ongoing experimentation on messaging, offers, timing, targeting, and conversion experiences.

• Assess the incremental impact on customer behavior and business outcomes using appropriate controls.

• Define customer data, behavioral signals, and reporting necessities.

• Guide data-team priorities and requirements, ensure data usability, and translate findings into actionable strategies.

• Collaborate with Product to refine features and customer experiences that enhance engagement, retention, and reactivation.

• Align Sales and Customer Service on outreach strategies, offers, handoffs, and necessary operational changes.

• Communicate effectively and ensure consistent execution across marketing and interpersonal interactions.

• Construct and maintain performance reports, communicating results and priorities to leadership.

• Continuously adopt and develop AI tools and automations to enhance the speed, quality, and scalability of retention marketing.

⛳️ Requirements

• Proven success in personally developing and scaling retention marketing programs that significantly enhance retention, reactivation, and customer lifetime value.

• In-depth knowledge of subscription retention dynamics, including activation, product adoption, ongoing engagement, renewal, and winback strategies.

• Experience in translating software capabilities and customer behaviors into impactful marketing initiatives; consumer subscription experience is advantageous.

• Exceptional customer insight and product understanding.

• Daily, fluent application of generative AI in customer research, audience and insight analysis, copy and creative production, landing page development, experimentation, and automation.

• Ability to showcase real campaigns, pages, and tools developed through AI-assisted workflows.

• Working proficiency with AI-native builder tools such as Cursor, Claude Code, Codex, Vercel, Netlify, and Supabase.

• Strong skills in copywriting and conversion rate optimization.

• Robust quantitative skills and experience in defining customer segments, lifecycle metrics, and experiment measurement.

• Capability to analyze outcomes and convert customer data gaps into actionable requirements for data and engineering teams.

• Excellent written and verbal communication skills.

• Highly organized, proactive operator who excels in ambiguous situations with minimal guidance.

• Alignment with Nerdy’s nonpartisan, mission-driven culture.

🏝️ Benefits

• Competitive compensation.

• Clear pathways for promotion.

• Equity (RSUs).

• 401(k) plan with company matching and immediate vesting.

• Remote-first culture that accommodates various time zones and working styles.

• Flexible time off policy.

• Comprehensive learning membership for the employee and their household, including 1:1 tutoring hours, unlimited on-demand classes, and a full range of learning products and services.

• Access to advanced AI tools.

• Medical, dental, vision, life insurance, short-term disability, and long-term disability coverage.

• Maternity, paternity, and adoption leave benefits.