Senior Director, Retention Marketing (remote)

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

All Jobs > Senior Director, Retention Marketing

Full-time

Description

Nerdy is looking for a Senior Director, Retention Marketing to join our team! As Senior Director of Retention Marketing, you’ll take full ownership of how Nerdy engages its current and former customers, from first activation through renewal and winback. This is a high-impact individual contributor role with no direct reports: you build our email and communication plans, processes, tools, and automations, and then execute successfully. You’ll launch programs that keep customers engaged, bring lapsed customers back, and increase lifetime value.

We’re looking for a marketer who pairs sharp customer and product insight with strong messaging, analytical rigor, and a builder’s mindset. You’re a top‑tier, AI‑native marketer who personally creates and ships campaigns, customer journeys, and landing pages. Partnering closely with Product, Sales, Customer Retention, and BI teams, you’ll turn what customers tell us into compelling reasons to stay, engage, and maximize usage of our learning platform and products.

This role is a remote role, based in the United States.

About Nerdy

At Nerdy (NYSE: NRDY) - the company behind Varsity Tutors - we’re redrawing the blueprint of learning. Our Live + AI™ platform fuses real-time human expertise with proprietary generative‑AI systems, setting a new bar for measurable academic impact at global scale.

We recruit the kind of technologists and operators you’d bet on as solo founders - people who turn ambiguous problems into shipping code, iterate faster than markets move, and compound their advantage with every data point. In an era where great employees can deliver 10‑times the leverage of the merely good, we back those who play to win.

Fortune favors the bold. Join us.

How we compete

• AI‑Native at every level
  From the CEO to day‑one hires, everyone builds and ships with generative AI. If you’re not wielding AI, you’re not done.
• Entrepreneurial velocity
  Move at founder speed, prototype in hours, and measure in real user outcomes. Slow teams die.
• Free‑market rigor
  Ideas rise or fall on merit and results - no committees, no politics, no cap on upside.
• Full‑stack ownership
  You design, build, and run what you ship; accountability is a feature, not a bug.
• Reward for contribution
  Pay rises with impact, not years. Outstanding results earn outsized rewards. We evaluate both what you achieve and how you achieve it: living our leadership principles and using AI effectively are formally measured and rewarded.
• Relentless exploration
  Push the frontier of generative AI in live learning and - because only the paranoid survive - questioning every legacy assumption along the way.
• Is Apolitical
  You stay focused on mission‑aligned outcomes, not distractions or unrelated causes.

If you’re a technically minded builder who thrives on open competition, personal responsibility, and the chance to redefine how the world learns - while continually stretching the limits of what generative AI can do - come do the most ambitious and rewarding work of your career here. Learn more at nerdy.com.

Nerdy’s shareholder letters below explain our latest products and strategy:

• 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.

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.

Unleash Your Potential at Nerdy

At Nerdy, you'll earn your success through meritocracy and exceptional outcomes. Our benefits reward performance and initiative:

• 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. Remote role, based in the United States.
• 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.

The Bottom Line

If you're driven by impact, energized by ownership, and excited to help shape what’s next, you’ll thrive here. We move fast, think big, and reward those who deliver. This isn’t a traditional corporate environment - it’s a place to do the most meaningful work of your career.