Enterprise Account Executive (Full Cycle)

Job Description

Chegg Skills helps working adults build the skills they need to access better jobs—faster and more affordably. We’ve already helped thousands of learners advance their careers through partnerships with leading employers, education platforms, and workforce marketplaces. Our programs combine expert-led instruction, hands-on practice, and personalized support, with a focus on relevance, outcomes, and flexibility.

Now, we’re expanding into new direct B2B partnerships, launching offerings for employer upskilling and workforce mobility. That’s where you come in.

We’re hiring an Enterprise Account Executive (Full Cycle) to build our direct B2B partnerships from the ground up. You will own the full sales process: sourcing leads, testing market demand, closing deals, and ensuring the revenue is realized. This is not just a closing role—you will play a key role in shaping our go-to-market strategy through real-time customer feedback.

We are looking for someone who is excited to sell ahead of the curve, navigate ambiguous product-market fit conversations, and partner closely with product and services teams to help define where Chegg Skills goes next.

• Own the entire direct B2B sales cycle—from prospecting and initial outreach to signed contract and revenue realization.

• Test the market: Help identify the right customer segments, messaging, and offer design through real-time selling.

• Provide structured feedback to Product, Marketing, and Services teams to shape roadmap and go-to-market materials.

• Collaborate with internal teams to ensure new deals are scoped for success, with operational plans in place to deliver on promises.

• Track pipeline, forecast accurately, and report on key metrics including qualified opportunities, closed-won deals, and revenue milestones.

• 5+ years of B2B sales experience, ideally in edtech, SaaS, or workforce development.

• Proven track record of closing new business and owning revenue delivery, not just signed deals.

• Experience selling into ambiguous, evolving product spaces.

• Strong commercial instincts: you know when to push, when to listen, and how to build urgency.

• High accountability and CRM rigor.

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.

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