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Role Description

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.

• 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.

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).

Requirements

• 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.

Benefits

• 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.