Senior Product Manager (AI-Native)

Overview of the role:

At Nerdy, we’re on a mission to help people learn—and we’re looking for a Senior Product Manager (AI-Native) to help drive greater learner engagement on our Live+AI learning platform. We are looking for someone who is equal parts data-driven strategist, customer advocate, and retention architect. In this role, you’ll drive measurable retention by ensuring every parent and student consistently discovers—and acts on—the next best learning opportunity across our platform. You’ll work with curiosity, tackle ambiguity head-on, and cross-functionally to turn complex problems into seamless learning experiences that deliver real value.

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:

• 5+ years of product and/or business leadership experience, specifically working on or adjacent to consumer software products.

• Analytical and quantitative skills; experience getting and using data and metrics to test theories, confirm assumptions, and measure success.

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

• Self-starter with a strong bias for action and the ability to drive results in a fast-paced, dynamic environment.

• Strong verbal and written communication skills.

• Comfortable with a fast-paced, ambiguous environment and the ability to manage multiple, competing priorities simultaneously.

• Proven ability to identify, analyze, and solve ambiguous problems with high attention to detail.

• Excellent collaboration skills that enable you to earn trust at all levels.

Responsibilities:

• Map the parent and student journeys (e.g. onboarding, great sessions, weak sessions, pre-exam crunch, seasonal lulls, etc.) and cohorts to understand our biggest engagement and retention opportunities

• Convert data from tutoring sessions, sales transcripts, and product behavior into dynamic segments and intents that tell us who needs what and when.

• Leverage our internal data, internal product and marketing messaging guidance, and new AI tools to automate and dynamically create highly personalized content.

• 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.

• Ensure every message is personal and actionable, clearly advancing the learner’s goals.

• Set bold targets for engagement, tutoring session consumption, and retention uplift; instrument real-time dashboards that expose progress.

• Run rapid A/B tests across modalities, channels, and timing; double-down on winning plays and codify them into repeatable playbooks.

• Integrate emerging AI tools that improve targeting accuracy, experimentation speed, and operational efficiency.

Leadership & Culture Expectations:

You will embody and promote Nerdy’s leadership principles:

• Goes Deep: You engage directly with data and performance metrics to understand underlying drivers.

• Delivers Results: You turn strategy into execution, maintaining high quality even amid ambiguity.

• Bias for Action: You make decisions quickly, test early, and iterate rapidly.

• Builds Trust: You lead with clarity, humility, and transparency.

• Thinks Big: You imagine bold futures and identify transformative product opportunities.

• Is Apolitical: You focus on outcomes that move the business and the learner experience forward.

You can learn more about all of our Leadership Principles and culture  here.

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.