Edtech.com's Summary

Chegg is hiring an Enterprise Account Executive (Full Cycle) to lead and execute the entire direct B2B sales process, from sourcing leads to closing deals and ensuring revenue realization. The role involves testing market demand, providing customer feedback to shape product and go-to-market strategy, and collaborating with internal teams to deliver on commitments.

Highlights

Own the full B2B sales cycle including prospecting, outreach, contract signing, and revenue realization.
Test and identify optimal customer segments, messaging, and offer design through active selling.
Provide structured feedback to Product, Marketing, and Services teams to inform roadmap and sales materials.
Collaborate internally to scope new deals and ensure operational plans support successful delivery.
Track sales pipeline, forecast accurately, and report on qualified opportunities, closed deals, and revenue milestones.
Requires 5+ years of B2B sales experience, ideally in edtech, SaaS, or workforce development.
Proven track record of closing new business with accountability for revenue delivery.
Experience selling in ambiguous and evolving product environments.
Strong commercial instincts with high accountability and CRM discipline.
Focus on building direct B2B partnerships in employer upskilling and workforce mobility sectors.

Enterprise Account Executive (Full Cycle) Full Description

Enterprise Account Executive (Full Cycle)

United States Remote

Full time

Job Description

About Chegg Skills

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.

The Role

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.

Key Responsibilities

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.

What You Bring

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, Thinkful Online Learning, 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/

Thinkful (a Chegg Online Learning Service): https://www.thinkful.com/about/#careers

Chegg out our culture and benefits!

http://www.chegg.com/about/working-at-chegg/benefits/

Chegg is an equal opportunity employer

Original Job Description