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

This role exists to own that distinction, create demand across multiple channels, and help turn Chegg Skills into a clearly understood, trusted, and desired brand for learners, employers, and partners.

We are looking for a Head of Marketing who is equal parts strategist, builder, and doer — someone who can think big, move fast, and execute relentlessly in an ambiguous environment.

Why This Role Matters

This is a chance to shape a brand at an inflection point. You will not inherit a finished system. You will help build it.

The impact of this role will be visible, measurable, and meaningful.

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

What You’ll Own

Brand & Positioning

Define and evolve the Chegg Skills brand with clarity and conviction
Create clear brand delineation between Chegg Skills and Chegg’s legacy consumer business
Establish a narrative that earns trust with learners, employers, and institutional buyers
Own messaging architecture, voice, tone, and positioning across all channels
Build credibility in a space crowded with noise, skepticism, and look-alike competitors

Demand Generation & Growth

Drive measurable demand and pipeline across:

Direct-to-consumer learners

B2B buyers (employers, institutions, partners)

Channel and marketplace partners
Design and execute campaigns that generate awareness, leads, and revenue
Balance brand building with performance marketing, without sacrificing either
Build strong content, lifecycle, and go-to-market motions that scale

Strategy & Speed

Develop a clear marketing strategy tied to business goals and revenue outcomes
Rapidly test, learn, and shift strategy as the market evolves
Make smart bets with imperfect data and adjust quickly
Bring order where needed, without slowing momentum

Sales & Revenue Partnership

Operate as a true partner to Sales, not a downstream service function
Align on ICPs, buyer journeys, enablement, and feedback loops
Help create the conditions for sales success through clarity, credibility, and demand
Be comfortable in healthy tension and shared accountability

Leadership & Execution

Build and lead a high-performing, low-ego marketing team
Be hands-on and willing to get in the weeds when needed
Set standards, processes, and operating rhythms that actually work
Create a culture of ownership, creativity, accountability, and speed

Who You Are

You have led marketing in high-growth, ambiguous environments, ideally where brand transformation was required
You know how to build brand and generate demand at the same time
You are creative, but grounded in execution and results
You are strategic, but not precious about plans
You are process-oriented, but never process-bound
You are scrappy, resourceful, and biased toward action
You are comfortable operating inside a larger company while building something that feels like a startup
You thrive when the answer is not obvious and the path is not linear

What Great Looks Like in This Role

The market clearly understands what Chegg Skills is and why it matters
Chegg Skills has its own identity, credibility, and momentum, distinct from big Chegg
Sales has consistent, high-quality demand and clear positioning to sell against
Partners see Chegg Skills as a serious, differentiated player
The marketing team moves fast, learns fast, and ships real work
Strategy and execution stay tightly connected to business outcomes

The base salary pay range for this position is $195,000 to $285,000. 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.