Sales Director

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 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.

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