Director of Engineering (AI-Native)

NerdyRemote - USA+ Equity5d ago

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Requirements

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.

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.
Retirement Made Simple:
A Remote-First Culture: We embrace flexibility across time zones and working styles to attract top talent and meet learners where they are.
A Remote-First Culture:
Flexible Time Off: Recharge on your terms, ensuring maximum productivity.
Flexible Time Off:
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.
Continuous Learning:
Supercharge with AI: Leverage cutting-edge AI tools to accelerate your workflow.
Supercharge with AI:
You’re Covered: Medical, dental, vision, life, STD & LTD plans plus strong maternity, paternity, and adoption leaves - numerous options for you and your family.
You’re Covered:
The Bottom Line:
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.