Nerdy

Lead multiple engineering teams to develop AI-native web applications and sales tools, ensuring peak performance during critical sales periods. | 8+ years in software engineering, 4+ years leading engineering teams, experience with web applications, APIs, distributed systems, and AI tools. | 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.

Lead and manage a team of retention specialists to reduce churn and improve customer lifetime value through coaching, performance management, and process improvements. | 3-5 years in customer retention or sales with 2+ years managing frontline teams, strong coaching skills, data fluency, CRM experience, and ability to work flexible hours. | Overview of Position Varsity Tutors is seeking a Customer Retention Manager to join our team! The Customer Retention Manager will have a direct impact on business growth as we help more people achieve their academic goals and help us continue our national expansion. The Customer Retention Manager will lead a team of Retention Specialists focused on saving at-risk memberships, reducing churn, and improving lifetime value. This role drives day-to-day coaching, performance management, and process excellence across cancellations, downgrades, pauses, and escalations, partnering closely with our Customer Escalations team. About Nerdy: Nerdy (NYSE: NRDY), the parent company of Varsity Tutors, is a leading platform for live online learning, with a mission to transform the way people learn through technology. The Company's purpose-built proprietary platform leverages technology, including AI, to connect learners of all ages to experts, delivering superior value on both sides of the network. Nerdy's comprehensive learning destination provides learning experiences across 3,000+ subjects and multiple formats—including one-on-one instruction, small group classes, large format group classes, and adaptive self-study. Nerdy's flagship business, Varsity Tutors, is one of the nation's largest platforms for live online tutoring and classes. Its solutions are available directly to students and consumers, as well as through schools and other institutions. Nerdy is a publicly traded company on the New York Stock Exchange. Learn more about Nerdy at https://www.nerdy.com/. Nerdy's shareholder letters below explain the product and strategy and are the most effective way to learn about what the company is building. • Q1-2025 Shareholder Letter • Q4-2024 Shareholder Letter • Q3-2024 Shareholder Letter Qualifications: • 3 to 5 years in customer retention or sales center with at least 2 years managing a frontline team • Comfortable in an ambiguous, face paced environment • Proven results improving save rate and reducing churn in a subscription or membership business • Strong coaching skills with a track record of lifting the middle and addressing underperformance within structured timelines • Data fluency across funnel and revenue metrics, comfortable building and interpreting KPI dashboards • Excellent communication, conflict resolution, and de-escalation skills • Experience with modern CRM and contact center tools (Zendesk, Looker) • Demonstrated ability to implement and train teams in strategic and effective retention techniques • Ability to work evenings and weekends as required • Embraces and supports Nerdy as an apolitical company and recognizes that we can have the largest impact if we are united in our focus on helping people learn and not divided or distracted by advancing unrelated causes Responsibilities: • Own team performance on retention KPIs, including lost revenue, 24 hour repeat and processed rates • Manage a team of Retention Specialists, including hiring, onboarding, weekly coaching, and performance reviews • Monitor call quality and compliance, provide real-time feedback, and run targeted skill clinics on objection handling, value reinforcement, and product fit • Optimize workflows for cancellations, pauses, and downgrades, ensure accurate attribution and documentation in CRM • Partner with Escalations for complex cases, resolve customer issues quickly, and prevent repeat contacts • Collaborate with SalesOps to track impact and to refine reporting • Execute Back-to-School and other seasonal playbooks, including mindset reframing, messaging pillars, track-specific scripts, and feature positioning by grade level • Drive test-and-learn experiments on scripts, offers, and save strategies, and roll out wins with clear SOP updates • Manage intraday performance, manage schedules, and maintain service levels and response times • Represent Retention in cross-functional forums, share voice-of-customer insights, and inform product and policy changes Leadership & Culture Expectations: You will embody and promote Nerdy's leadership principles: • Goes Deep: You personally engage with metrics, audits, and data, ensuring you understand the "why" behind performance variances. • Delivers Results: You move from strategy to execution quickly, ensuring timelines and quality stay high—even in ambiguity. • Bias for Action: You experiment, prototype, and adjust quickly. You make the call when the path isn't fully clear. • Builds Teams: You prioritize talent development, succession planning, and cross-functional collaboration. • Builds Trust & Communicates Openly: You lead with transparency, humility, and clarity. • Thinks Big & Innovates: You challenge the status quo, bring fresh ideas, and embrace emerging technologies. • Is Apolitical: You stay focused on mission-aligned outcomes, not distractions or unrelated causes. You can learn more about all of our Leadership Principles and culture here. Unlock Your Full Potential at Nerdy: At Nerdy, we're not just transforming education—we're transforming your life. Our benefits package is built with a forward-thinking, "focus on you" mindset, so you can be your healthiest, happiest, and yes, most super-human self. Here's a snapshot of what we offer: • Competitive Compensation: Enjoy a competitive salary paired with performance based variable compensation. • Comprehensive Healthcare: Choose from top-tier medical, dental, vision, and life insurance plans designed to keep you and your family covered. • Retirement Made Simple: Benefit from our 401(k) plan with an immediate company match—no vesting delays! • Family First: Generous maternity, paternity, and adoption leave ensure you have the support you need at life's big moments. • Flexible Time Off: Our flexible PTO lets you recharge on your own terms and when you need it the most. • 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).