Job Description

We’re looking for a proactive, highly organized Executive Assistant to partner directly with our Chief Technology Officer (CTO) and provide broad administrative support to his leadership team — five Vice Presidents across Engineering, Product, and Design, as well as our VP of Institutional Sales. This is a high-impact role supporting one of Nerdy’s most innovative, fast-moving, and dynamic executive teams.

Our CTO’s style is entrepreneurial, people-centric, and fast-paced. His leadership team brings a diverse range of working styles, from direct and structured to relational and collaborative, high-velocity execution to visionary and creative thinking. You’ll need to navigate shifting priorities, tailor your support style across leaders, and create a sense of order in a fast-moving, constantly evolving environment.

This role is ideal for someone who thrives in high-growth settings, enjoys building trusted relationships across functions, and brings a calm, resourceful approach to executive support. The right candidate will anticipate needs, communicate with confidence, and bring a high level of discretion and professionalism to every interaction.

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.

Qualifications:

We’re looking for an Executive Assistant who thrives in a dynamic, fast-paced environment, is highly organized, and can balance multiple competing priorities. The ideal candidate will possess strong communication skills and a proactive mindset that enables them to think ahead and solve problems effectively.

• 5+ years executive assistant experience supporting C-level executives, specifically CTO/CPO.
• Experience in fast-paced startup environment, preferably founder-led.
• Proven ability to support multiple senior leaders simultaneously.
• Experience with AI tools for workflow optimization and task automation.
• Strong written/verbal communication skills.
• Exceptional organizational abilities and attention to detail.
• Ability to work independently and prioritize competing demands.
• Experience managing teams of 100+ employees (indirect support).

Preferred Qualifications

• Project management experience.
• Familiarity with engineering/product/UX development workflows.

Responsibilities:

• Provide proactive, high-quality administrative support to the CTO, including calendar management, travel coordination, meeting preparation, and day-to-day prioritization.
• Serve as a point of coordination and support for the CTO’s leadership team (VPs across Engineering, Product, and Design), adjusting your approach based on each leader’s unique working style.
• Offer support to the VP of Institutional Sales, including scheduling, coordination, and logistics.
• Manage confidential and sensitive information with discretion, sound judgment, and professionalism.
• Coordinate cross-functional meetings, strategic initiatives, and project timelines to ensure follow-through and execution.
• Plan and execute internal events, team offsites, and key department-wide communications in collaboration with People Ops and other EAs.
• Prepare materials, agendas, decks, and background research for meetings, presentations, and leadership communications.
• Track budgets, process expense reports, and support purchasing and vendor logistics as needed.
• Identify and implement opportunities to streamline workflows through automation and AI tools.
• Partner closely with the Chief of Staff, HR Business Partner, and broader EA team to ensure alignment and consistency across the organization.

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.

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