About The Princeton Review: The Princeton Review/Tutor.com is a leading tutoring, test prep, and college admission services company. Every year, it helps millions of college- and graduate school–bound students achieve their education and career goals through online and in-person courses delivered by a network of more than 4,000 teachers and tutors, online resources, and its more than 150 print and digital books published by Penguin Random House. The company’s Tutor.com brand is one of the largest online tutoring services in the U.S. It comprises a community of thousands of tutors who have delivered more than 22 million one-to-one tutoring sessions. The Princeton Review is headquartered in New York, NY. Follow the company on LinkedIn, YouTube and Instagram.

Summary of Position: 

This role oversees a team of Sales Representatives, ensuring strong pipeline development, forecasting accuracy, market expansion, and high-quality execution of the full sales cycle. The Director works cross-functionally with Marketing, Client Success, Product, Learning Services, and Sales Operations to position Tutor.com as the premier partner for academic intervention and student support.

The ideal candidate brings deep knowledge of K–12 funding, academic challenges, tiered interventions, tutoring operations, and district procurement processes – paired with the ability to coach, lead, and scale a high-performing sales team.

Key Responsibilities:

Sales Leadership & Strategic Direction

• Lead, develop, and manage a team of Sales Representatives responsible for selling K–12 On-Demand and High-Dosage Tutoring programs.

• Establish and execute a comprehensive go-to-market strategy aligned with institutional revenue goals, market trends, and district needs.

• Own multimillion-dollar annual sales and revenue targets with accountability for YoY growth and market penetration.

• Design sales playbooks, territory strategies, and campaigns that drive consistent pipeline generation and execution.

• Conduct monthly and quarterly business reviews, evaluating performance, win/loss trends, and market opportunities.

Team Management & Coaching

• Recruit, train, onboard, and develop top-performing Sales Representatives using structured, scalable frameworks.

• Provide weekly coaching, deal reviews, skill-building sessions, and ongoing professional development.

• Establish clear KPIs, activity expectations, and performance standards to ensure team members meet sales goals.

• Foster a positive, collaborative, accountable culture with high communication standards.

High-Dosage Tutoring & Academic Intervention Expertise

• Oversee the positioning, pricing, and strategic packaging of High-Dosage Tutoring as an evidence-based tiered intervention aligned to district academic priorities.

• Partner with districts to align Tutor.com solutions to ESSA evidence requirements, accountability metrics, and instructional goals.

• Ensure the team can articulate operational logistics such as tutor staffing, scheduling, reporting, SSO implementation, and progress monitoring.

Market Expansion & District Engagement

• Identify emerging state and district tutoring initiatives, grant opportunities, and funding pathways (Title I, state tutoring grants, etc.).

• Expand Tutor.com's presence across key regions, large districts, and high-need markets.

• Build and maintain executive-level relationships with superintendents, CAOs, curriculum leaders, federal programs directors, and intervention teams.

• Represent Tutor.com at national and regional conferences, consortium events, and K–12 leadership forums.

Cross-Functional Collaboration

• Partner with Marketing on lead-generation strategies, webinar programs, campaigns, and district-facing content.

• Collaborate with Product and Operations to optimize product-market fit for tutoring, scheduling models, reporting capabilities, and integration requirements.

• Work closely with Client Success to ensure smooth implementations, long-term satisfaction, strong outcomes, and expansion opportunities.

• Provide leadership across cross-functional initiatives that strengthen Tutor.com’s academic tutoring portfolio.

Forecasting & Revenue Planning

• Own the weekly, monthly, and quarterly forecasting for the K–12 tutoring business, ensuring accuracy, transparency, and discipline across the team.

• Conduct pipeline reviews to assess opportunity health, risk mitigation, and strategic prioritization.

• Maintain strong Salesforce hygiene and reporting consistency across the team.

• Partner with Finance and executive leadership on annual planning, revenue modeling, and growth scenarios.

• Use data-driven insights (sales velocity, conversion rates, pipeline coverage, forecast variance) to drive constant improvement.

Education, Background, Experience & Qualifications

Minimum Qualifications

• Bachelor’s degree or equivalent experience.

• 7–10+ years of successful B2B or EdTech sales experience, with at least 3–5 years in a management or director-level role.

• Track record of leading sales teams to exceed multimillion-dollar revenue targets.

• Deep knowledge of K–12 district operations, funding sources, academic intervention programs, and tutoring models.

• Advanced skill in consultative selling, strategic planning, and executive communication.

• Proficiency in Salesforce, Excel, PowerPoint, and CRM-driven forecasting.

• Ability to travel regularly for district visits, conferences, and team leadership activities.

• Experience leading sales teams within tutoring, intervention, or academic support Experience with RFP leadership, state contracting, and complex procurement cycles.
• Strong collaboration experience with Product, Operations, and Client Success teams.

The Princeton Review is an equal employment opportunity employer. The Princeton Review’s policy is not to discriminate against any applicant or employee based on race, color, religion, national origin, gender, sexual orientation, gender identity or expression, age, marital status, disability, military status, genetic information, or any other basis protected by applicable law. The Princeton Review also prohibits harassment of applicants or employees based on any of these protected categories. It is also The Princeton Review’s policy to comply with all applicable laws respecting consideration of unemployment status in making hiring decisions.

Please include your resume and a cover letter, addressed to John Calvello, outlining how your skills and experience meet the qualifications of the position and why you are interested in this role. Please indicate any Salesforce certifications you have earned.

The Princeton Review offers a competitive salary and benefits package, commensurate with experience and skills. The salary for this position will be $91,000-$152,000 per year.