Principal, Sales and Operations Planning

Overview:

Nerdy is searching for a Principal, Sales and Operations Planning to join our team. In this high-leverage individual contributor role, you will own the strategy, systems, and forecasting engine that power Nerdy’s customer-facing operations. You will develop and maintain sophisticated forecasting models by leveraging advanced techniques such as exponential smoothing, Monte Carlo simulation, and machine-learning–based automation—to improve forecast accuracy and inform critical operational and strategic decisions. Drawing on these insights, you will build robust capacity plans, optimize workforce mix and shift structures, and design data-driven scheduling models that improve service quality while reducing labor cost through greater efficiency.

A core part of this role is leading workforce planning initiatives that span capacity modeling, skill-based staffing optimization, part-time workforce deployment, and shift-design refinement. Your work will help maximize service quality while aligning labor needs with demand patterns, and you will drive cost-optimization efforts by deeply analyzing staffing models, overtime trends, full-time vs. part-time mix, intra-day performance, and service-level risks. As operational needs evolve, you will design and implement automated workflows and systems—such as streamlined PTO/VTO processes, schedule adjudication tools, and dynamic compensation platforms to improve scalability, speed, and decision quality.

You will turn ambiguous problems into clear, measurable operating plans and establish a consistent S&OP cadence that brings predictability and transparency to planning. This requires strong cross-functional partnership: you will collaborate closely with Sales, Marketing, Finance, Product, Operations, and Training to align on assumptions, KPIs, operational changes, and resourcing strategies. You will also build and refine dashboards and reporting frameworks including WBR reporting and forecast-accuracy monitoring that surface emerging trends, driver insights, and performance metrics for leadership.

Success in this role means building a scalable planning foundation for Nerdy’s Sales and Member Services teams, identifying risks and opportunities early, and enabling measurable improvements in performance, efficiency, and operating discipline. You will regularly translate complex analytical insights into concise, actionable recommendations for senior leaders, while guiding the broader evolution of Nerdy’s planning capabilities, processes, tools, and AI-driven automation.

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:

• Bachelor’s degree required; Master’s preferred.

• 8+ years in Sales/Revenue/Market Operations and analytics.

• Proven experience in forecasting models, workforce planning, and routing strategies.

• Expertise in funnel analytics, advanced BI tools, and SQL proficiency.

• Hands-on experience with CRM and engagement tools like Salesforce/HubSpot.

• Proven track record designing and managing sales compensation programs.

• Strong change management skills in fast-paced environments.

• Excellent communicator with executive storytelling skills.

• Experience with AI-native productivity and quality tools.

• Alignment with company mission and outcomes-focused culture.

Responsibilities:

• Lead workforce planning initiatives, including capacity modeling (W+1 through W+2), skill-based staffing optimization, part-time workforce deployment, and shift design optimization to improve labor efficiency and service delivery.

• Develop, enhance, and maintain forecasting models—leveraging techniques such as exponential smoothing, Monte Carlo simulation, machine learning automation, and operational sensitivity analysis—to improve accuracy and support strategic decision-making.

• Drive cost-optimization efforts by analyzing staffing models, overtime trends, full-time vs. part-time mixes, service-level risks, and intra-day operational performance to recommend actionable cost-saving strategies.

• Partner cross-functionally with Operations, Finance, Training, and Technology teams to align on staffing assumptions, operational changes, and performance metrics while ensuring clear communication of timelines, risks, and results.

• Build and optimize operational dashboards and reporting mechanisms (e.g., WBR, forecast accuracy, BI tools) that provide visibility into trends, drivers, KPIs, and performance insights for leadership.

• Design, implement, and improve automated workflows—including PTO/VTO approval processes, schedule adjudication, and dynamic compensation (ADC) platforms—to streamline workforce management and enhance operational scalability.

• Build and maintain operating cadence including reviews and audits.

• Lead workforce planning for inbound/outbound sales teams.

• Scale processes via automation and AI with compliance guardrails.

• Partner on CRM architecture, integrations, and change management.

• Establish experimentation frameworks and scale successful initiatives.

• Lead cross-functional initiatives impacting revenue and customer experience.

• Deliver executive-level insights and communicate trade-offs and risks.

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.