Senior Director, Retention Marketing

Responsibilities

• Own retention marketing strategy and execution across onboarding, engagement, retention, renewal, winback, upsell, cross-sell, and referrals.
• Develop a deep understanding of our customers and products through customer research, behavioral analysis, and close partnership with customer-facing teams. Identify where customers encounter friction, miss value, or need a compelling reason to take the next step.
• Build and improve retention marketing programs across email, SMS, push notifications, and web experiences. Determine whom to reach, when to reach them, and what to say based on customer needs, behavior, and stage in the relationship.
• Personally create and launch customer communications, creative, landing pages, and automated journeys using AI-native tools, taking work from insight through execution and optimization.
• Run continuous experimentation on messaging, offers, timing, targeting, and conversion experiences. Use appropriate controls to measure incremental impact on customer behavior and business results.
• Define the customer data, behavioral signals, and reporting needed to make better decisions. Direct priorities and requirements for data teams, validate that the resulting data is usable, and turn findings into action.
• Partner closely with Product to shape features and customer experiences that support engagement, retention, and reactivation, connecting marketing programs to the value customers receive from the product.
• Align Sales and Customer Service on customer outreach, offers, handoffs, and operational changes. Communicate clearly and drive implementation so the customer experience is consistent across marketing and human interactions.
• Build and maintain performance reporting, communicate results and priorities to leadership, and continually improve programs based on evidence.
• Continuously adopt and build AI tools and automations that increase the speed, quality, and scale of retention marketing.

Requirements

• 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 is essential; consumer subscription experience is a plus.
• Exceptional customer judgment and product fluency. You uncover customer needs, motivations, and barriers, understand how the product addresses them, and translate that understanding into the right message, channel, and timing.
• Top 1% AI-native marketer: daily, fluent use of generative AI across the full workflow, including customer research, audience and insight analysis, copy and creative development, landing page creation, experimentation, and automation. You can point to real campaigns, pages, and tools you have built through AI-assisted workflows.
• Working proficiency with AI-native builder tools such as Cursor, Claude Code, Codex, Vercel, Netlify, and Supabase to independently ship landing pages, automations, and reporting tools.
• Strong copywriting and conversion rate optimization skills. You can personally write persuasive customer communications and landing pages, identify friction, and independently hypothesize, build, test, and optimize experiences that drive action.
• Strong quantitative fluency and experience defining customer segments, lifecycle metrics, and experiment measurement. You can analyze results yourself and translate gaps in customer data into clear, actionable requirements for data and engineering teams.
• Impeccable written and verbal communication. You can make a compelling case, align stakeholders across functions, communicate precise requirements, and drive changes through implementation without direct authority.
• Highly organized, hands-on operator who thrives with ambiguity and minimal support. You build the strategy and do the work, scaling your impact through AI, automation, and tooling.
• Alignment with Nerdy’s apolitical, mission-focused culture.

Benefits

• Competitive Compensation & Advancement: Market-leading salary paired with clear promotion pathways and equity (RSUs) - become an owner in our success.
• Retirement Made Simple: 401(k) plan with company match and immediate vesting.
• A Remote-First Culture: We embrace flexibility across time zones and working styles to attract top talent and meet learners where they are.
• Flexible Time Off: Recharge on your terms, ensuring maximum productivity.
• Continuous Learning: Access an all-inclusive learning membership for you and your household, including 1:1 tutoring hours, unlimited on-demand classes, and our full suite of learning products and services.
• Supercharge with AI: Leverage cutting-edge AI tools to accelerate your workflow.
• You’re Covered: Medical, dental, vision, life, STD & LTD plans plus strong maternity, paternity, and adoption leaves - numerous options for you and your family.