Principal Product Manager, A.I. for Tutors

Overview:

Our vision of Live + AI powers everything we do at Nerdy. As the Principal Product Manager, AI for Tutors, you will own the Tutor Copilot —the omnipresent, context-aware AI layer that proactively supercharges every one-to-one session delivered by the tutor. You’ll define and execute the roadmap for a powerful AI-based tutor assistant that isn’t just chat-enabled, but is omnipresent, is context aware and working side-by-side with the tutor helping them deliver effective sessions real time. Your mission is to ensure top-notch learning outcomes for our customers at scale, while preserving the accountability and human connection that only a great tutor can provide. You’ll move at startup pace, embracing ambiguity, running rapid experiments, and failing forward to deliver high-velocity AI innovations that delight tutors, boost session quality, and accelerate customer retention.

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:

• Prior experience leading AI/ML–powered products (chatbots, recommendation engines, real-time analytics) with measurable impact. Ability to collaborate with ML engineers and data scientists on model trade-offs, data pipelines, and inference architecture.
• Entrepreneurial sense with a proven track record of delivering results by driving cross-functional teams from hypothesis through rapid prototyping to scale.
• Strong analytical skills and a data-driven mindset: defining metrics, running A/B tests, and using both quantitative and qualitative insights to drive decisions.
• High empathy and a customer-centric approach; passionate about understanding and advocating for customers’ needs.
• Comfort with ambiguity and a bias for action; embrace a “fail forward” approach and iterate rapidly.
• Excellent communicator: skilled at distilling complex AI concepts for non-technical stakeholders, creating training materials, and presenting roadmaps and results to senior leaders.
• Startup prowess & agility: thrive in ambiguity and high-velocity environments—embrace “fail fast, learn fast,” pivot quickly, and keep teams aligned on outcomes.
• Passion for education innovation with a history of staying on top of cutting-edge AI research and tooling.

Responsibilities:

• Own the Tutor Copilot roadmap: define strategy and drive delivery of an omnipresent, context-aware AI assistant that proactively supports tutors during live sessions.
• Design and prioritize AI features by partner with design, engineering, ML engineering and data science.
• Lead rigorous experimentation by establishing A/B testing frameworks for proactive features, measure impact on session quality and tutor satisfaction, and iterate rapidly.
• Scale personalization by leveraging AI/ML to tailor interventions based on individual tutor-student history, making every suggestion highly relevant and actionable.
• Evangelize and train by creating demos, best-practice guides, and training materials to drive adoption of proactive Copilot features among tutors and internal stakeholders.
• Monitor emerging AI by continuously scouting and evaluating new technologies (e.g., speech analytics, computer vision for whiteboard content) to keep our products best-in-class.
• Advocate for outcomes by presenting roadmap progress and learnings to senior leadership, ensuring alignment on priorities that drive session quality, tutor engagement, and business growth.

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.