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 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.