Director of Engineering (AI-Native)

Overview: Nerdy is looking for an innovative Director of Software Engineering to lead our Consumer Acquisition engineering organization, owning the complete funnel from marketing website and lead generation through telesales and ecommerce conversion to new customer onboarding. You'll manage multiple engineering teams across the US, Canada, and LATAM, building the systems that drive millions in annual revenue for our consumer tutoring business. What You'll Own

• Sales Agent Tools: Internal applications for telesales conversion, post-sale onboarding, call/SMS handling, lead routing, and work distribution supporting 100+ concurrent agents
• AI-Powered Sales Automation: Jamie, our outbound AI voice agent that handles lead qualification and transfers to human agents, currently managing 80%+ of outbound dials
• Ecommerce & Self-Service: Self-service purchasing experiences, quotes checkout, and reactivation flows reducing sales CAC and expanding acquisition channels
• Marketing & Lead Generation: Consumer-facing websites, content management systems, landing pages, lead forms, and PPC/SEO optimization
• Communications & Operations: Email/SMS orchestration, call metrics, AI-powered scoring, business dashboards, alerting, and workforce management tools

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:

• Q3-2025 Shareholder Letter
• Q2-2025 Shareholder Letter
• Q1-2025 Shareholder Letter

Qualifications:

• 8+ years software engineering, 4+ years leading engineering teams.
• Experience managing multiple squads or 15+ person organizations.
• Experience managing remote or distributed teams across time zones.
• Strong agentic (LLM) coding skills and hands-on technical leadership; this role requires active involvement in code reviews, architecture decisions, and technical problem-solving.
• Track record shipping B2C/SaaS products at scale.
• Deep expertise in web applications, distributed systems, APIs.
• Proven ability to balance technical excellence with business delivery.
• Experience with sales tools, CRM, or marketing technology preferred.
• Experienced with AI-native tools that enhance productivity and speed (Cursor, Make.com, Supabase, Netlify, Claude Code, n8n, Firecrawl, ChatGPT, Grok, Bolt, Vercel, etc).

Technical Environment

• Architecture: Modern web applications, real-time agent systems, event-driven architecture with Kafka.
• Cloud: AWS-native infrastructure with Kubernetes.
• Integration-heavy: Twilio Flex (contact center), SMS/RCS messaging, Segment (CDP), Braze/SendGrid (communications), Regal (sales automation), Google/Meta Ads.
• Scale: High-traffic consumer web properties, 100+ concurrent sales agents, peak-driven traffic patterns.

Responsibilities:

• Ship features during critical sales periods.
• Drive platform simplification while solving immediate business needs.
• Build and retain high-performing engineering teams.
• Partner with Product, stakeholders, and executives across Marketing, Sales Operations, and Sales leadership.
• Represent engineering in executive planning and reviews.
• Manage multiple squads and staff engineers.
• Hands-on involvement in architecture, code reviews, and technical decisions.

What Success Looks Like

• Consistent delivery during peak periods.
• Measurable improvements in conversion, efficiency, or platform performance.
• Reduced complexity through strategic modernization.
• Strong cross-functional partnerships and team development.

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.