Chegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning. While we benefit from Chegg’s scale and credibility, we are intentionally distinct from “big Chegg” and its legacy.

This role exists to build, scale, and lead the revenue engine that will define Chegg Skills’ growth. We are looking for a Head of Sales who is more than a sales manager. This is a strategic, operational, and hands-on leader who can design systems, drive performance, coach teams, and close meaningful deals while navigating ambiguity.

What You’ll Own

Revenue Strategy & Growth

Build and execute a clear sales strategy aligned to company growth goals
Identify opportunities across markets, verticals, and channels
Develop prospecting and closing strategies across:

Direct B2B

Channel partners

Government

Higher education

Workforce and enterprise buyers
Translate market insight into revenue action

Sales Operations & Process Excellence

Design and implement scalable sales processes, playbooks, and operating rhythms
Own pipeline management, forecasting, and sales velocity metrics
Build systems that drive consistency, clarity, and performance
Establish clear performance standards and accountability frameworks
Create processes that connect Sales with Product, Marketing, Operations, Engineering, and Leadership

Team Leadership & Culture

Build and lead a high-performing, low-ego sales organization
Set the tone for culture, execution, and accountability
Lead daily standups, pipeline reviews, and deal strategy sessions
Facilitate deal swarms for high-value opportunities
Step into deals when needed and coach in real time
Develop talent through ongoing training, coaching, and performance management

Strategic Partnership

Partner closely with the Head of Marketing to align demand generation and revenue execution
Serve as a trusted consultant to leaders across the organization
Translate business priorities into clear sales motions and outcomes
Bring a revenue perspective to company-wide decisions

Execution in Ambiguity

Operate effectively in an environment that combines startup speed with enterprise complexity
Build structure where needed without slowing momentum
Make smart decisions with imperfect information and adjust quickly
Balance long-term strategy with immediate execution

Who You Are

You are not just a sales leader. You are a builder and architect of revenue systems.

Proven track record of building and scaling sales organizations
Deeply data-driven and detail-oriented
Experience designing sales processes, playbooks, and operating models from the ground up
Comfortable in strategy conversations and live deals
Understand GTM across multiple channels and buyer types
Skilled at coaching, training, and elevating sales talent
Respected as both a leader and a partner
Thrive in fast-moving, ambiguous environments
Scrappy, resourceful, and execution-focused

What Great Looks Like in This Role

A clear, repeatable, and scalable sales process exists across the organization
The pipeline is healthy, predictable, and aligned to revenue goals
Sales velocity, conversion, and deal quality improve consistently
The sales team is coached, confident, and accountable
Marketing and Sales operate as true partners
Product and other teams have strong feedback loops from the market
Revenue becomes a function of system strength, not individual heroics

Why This Role Matters

This is a defining role in building Chegg Skills’ growth engine. You will not inherit a finished system. You will design it, build it, and scale it.

If you are looking for comfort, this is not it.
If you are looking for ownership, influence, and the chance to build something meaningful, this is.

The On-Target Earnings (OTE) range for this position is $205,000 to $300,000, inclusive of any sales incentive, sales commission, or other form of variable compensation. Although this range represents the full range for the position, the actual pay will vary within this range based on geographic location, job type, professional experience, and other factors.

In addition, Chegg offers a comprehensive benefits plan for eligible employees, including medical, dental, vision, life and supplemental life insurance, short-and long-term disability, mental health support, parental leave, paid time off, paid holidays, 401(k) with matching contributions, Flexible Spending Account (FSA) and Health Savings Account (H.S.A.) options, an Employee Stock Purchase Plan, and other benefits found at: https://www.chegg.com/about/working-at-chegg/benefits/.

Why do we exist?

Students are working harder than ever before to stabilize their future. Our recent research study called State of the Student shows that nearly 3 out of 4 students are working to support themselves through college and 1 in 3 students feel pressure to spend more than they can afford. We founded our business on provided affordable textbook rental options to address these issues. Since then, we’ve expanded our offerings to supplement many facets of higher educational learning through Chegg Study, Chegg Math, Chegg Writing, Chegg Internships, Chegg Skills, and more to support students beyond their college experience. These offerings lower financial concerns for students by modernizing their learning experience. We exist so students everywhere have a smarter, faster, more affordable way to student.