Lead Security Engineer (AI-Native)

Overview

The Lead Security Engineer drives Nerdy’s enterprise security and infrastructure strategy to ensure scalable, secure, and reliable systems in a AWS first environment. This role combines strategic leadership and hands-on operational oversight to protect company assets, ensure compliance, and support high-growth business objectives.

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:

• Q4-2025 Shareholder Letter
• Q3-2025 Shareholder Letter
• Q2-2025 Shareholder Letter

Responsibilities:

• Define and execute enterprise security strategy
• Partner closely with leaders to cover compliance, automation, and security best practices across the organization
• Lead business continuity and disaster recovery planning
• Identify and address security gaps created by the rapid adoption of new tools and platforms
• Oversee threat detection, incident response, and vulnerability management
• Ensure regulatory, privacy, and data protection compliance
• Use AI-powered tools (e.g., Cursor, Claude Code, or equivalent) to implement security guardrails, automate checks, and accelerate security workflows
• Mentor other engineers and collaborate with peers to strengthen the team's collective knowledge
• Design secure, scalable, and resilient architecture
• Embed security controls across Engineering, Product, Legal, and People teams
• Manage vendors, security tools, and IT systems
• Report security posture and risk metrics to executives

Qualifications:

• 7+ years in Security Engineering, IT, or Infrastructure leadership
• Experience leading enterprise security in AWS-first environments
• Hands-on experience with AWS security (IAM, security groups, logging, monitoring)
• Strong knowledge of cybersecurity frameworks, risk, and compliance
• Experience leading threat detection, vulnerability management, and incident response
• Demonstrated ability to influence, driving security adoption across engineering and product teams
• Expertise in cloud infrastructure, IAM, endpoint and network security
• Explicit mentoring of senior-level engineers regularly
• Ability to align security strategy with business goals
• Strong executive communication and stakeholder management skills
• Experience using AI tools for security purposes with tools like Cursor, GitHub Copilot, Claude, or similar
• Bachelor’s in CS, Information Security, or related field (advanced degree/certs preferred
• Nice to have: Familiarity with NIST 800-171 and/or CMMC Level 2 compliance frameworks

Unleash Your Potential at Nerdy

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

• Competitive USD Compensation: Enjoy a market-leading rate paid in U.S. dollars.

• 100% Remote (Home Country Only): Work from anywhere in your home country—no relocation required, no borders crossed.

• Flexible Time Off: Our flexible PTO lets you recharge on your own terms and when you need it the most.

• Local Holiday Pay: We honor your nation’s official holidays with paid time off—celebrate what matters to you.

• Continuous Learning: Get a free, all-inclusive learning membership for you and your household—including 1-on-1 tutoring hours, unlimited on-demand classes, and access to our full suite of learning products and services.

• Supercharge with AI: Gain exclusive access to cutting-edge AI tools that boost your productivity, making you feel almost super-human (cape not included).

• Feedback-Rich, Collaborative Culture: Tap into regular training, peer reviews, and a team that treats every team member as a vital collaborator and owner in our success.

• Make a Global Impact: Your expertise fuels an innovative platform used by learners around the world—be part of something transformative.

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.