Job Description
The Opportunity
Chegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning.
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 Studentshows 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.
Video Shorts
Life at Chegg: http://youtu.be/Fwf90zgaOLA
Chegg Corporate Career Page: https://jobs.chegg.com/
Chegg India: http://www.cheggindia.com/
Chegg Israel: http://www.chegg.com/about/working-at-chegg/israel/
Chegg Skills: https://www.chegg.com/skills
Chegg out our culture and benefits!
http://www.chegg.com/about/working-at-chegg/benefits/
Chegg is an equal opportunity employer