Principal Product Manager (AI-Native)

Overview of the role:

Nerdy (NYSE: NRDY) is transforming how students learn—combining AI and live instruction across 3,000+ subjects. With 5M learners served through school partnerships and tens of thousands of families enrolled in Learning Memberships, we’re scaling fast—and retention is the frontier.

We are looking for an AI-native product leader to enhance engagement on our Live+AI learning platform. This is a high-impact opportunity to reinvent how students stay engaged, take action, and grow over time. You’ll lead retention product strategy across personalized nudges, in-product guidance, and post-session follow-ups—powered by internal data, LLMs, and real-time AI-generated signals.

This isn’t just about churn mitigation. It’s about activating momentum, one learner at a time.

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:

• Q1-2025 Shareholder Letter

• Q4-2024 Shareholder Letter

• Q3-2024 Shareholder Letter

Qualifications:

• Have 8+ years in product or growth roles, ideally in B2C SaaS, consumer tech, or subscription-based platforms.

• Are fluent in lifecycle thinking and activation/retention mechanics.

• Have worked closely with ML, marketing automation, or recommender systems.

• Love turning complex data into human-centered nudges that feel effortless to the user.

• Can write a clear one-pager, critique a message funnel, and wireframe a personalized dashboard—all in the same day.

• Have experience with tools like Iterable, Amplitude, Segment, Looker, dbt, and basic SQL.

• Experienced with AI-native tools that enhance productivity and speed (Cursor, Make.com, Supabase, Netlify, Claude Code, n8n, Firecrawl, ChatGPT, Grok, Bolt, Vercel, etc).

Responsibilities:

• Own and scale Nerdy’s cross-platform retention experience—from onboarding through active use, seasonal drop-offs, and exam prep peaks.

• Design journey-aware automations that guide parents and students to the next best action using AI, behavior signals, and NLP-derived session insights

• Map learning intents and cohorts from tutoring transcripts, product telemetry, and CRM behaviors; use these signals to trigger intelligent outreach.

• Use GenAI tools (Claude, GPT-4, internal LLMs) to create high-variance personalized content (session recaps, nudges, next-steps) at scale.

• Orchestrate multi-channel engagement: in-app, email, SMS, push, web—balancing impact, timing, and cognitive load.

• Build and iterate A/B experiments across every touchpoint modality—shipping, learning, and systematizing what works.

• Partner with Engineering, Customer Retention, and Data Science to scale a durable, personalized retention engine.

• Set measurable targets (consumption, session recurrence, LTV uplift), own dashboards, and track leading indicators.

• Constantly explore new AI tools, pilots, and workflows to increase speed and surface precision.

• Orchestrate cross-channel touchpoints (email, SMS, push, in-product prompts) that drive learners to do things like:

• Schedule and attend tutoring sessions.

• Review their AI-generated past session summaries.

• Complete personalized practice problems.

• Preview and edit next-session AI lesson plans.

• Enroll in group courses or other new features.

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.

• 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.