Edtech.com's Summary

Chegg is hiring a Sales Leader (Contract/Contingent Worker) to drive revenue growth and establish an early go-to-market foundation for Chegg Skills' new B2B partnerships. The role involves carrying a sales quota, closing deals across government, enterprise, or partner channels, coaching new sales representatives, and continuously refining sales strategies based on market feedback.

Highlights

Own revenue targets with channel focus on government, enterprise, or partner accounts.
Execute the full sales cycle from prospecting to closing deals.
Enable and coach two new sales hires, providing them with tools and playbooks.
Establish reporting, pipeline management, and forecasting systems.
Iterate on Ideal Customer Profiles (ICPs), messaging, and channel strategies from active sales insights.
Proven success in quota-carrying sales roles, especially in B2B or channel sales.
Experience building sales infrastructure in early or evolving GTM environments.
History of closing complex deals; government or enterprise sales experience preferred.
Contract term is full-time, initially six months with potential extension or conversion to full-time employment.
Compensation includes a balance of stable base and performance incentives (details finalized separately).

Sales Leader (Contract/Contingent Worker) Full Description

Sales Leader (Contract/Contingent Worker)

United States Remote

Full time

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.

About the role
We’re hiring a quota-carrying Sales Leader (Contract) to accelerate revenue and we stand up an early GTM foundation. You’ll own a number personally and act as a player-coach: closing deals, helping new reps ramp, and creating tight feedback loops to Product and Leadership. Expected channels may include government, enterprise, and partners.

Responsibilities

Revenue ownership: Carry a quota with clear channel ownership (government, enterprise, or partner accounts as assigned).
Deal execution: Prospect, run cycles, negotiate, and close.
Rep enablement: Make sure the two new hires have systems, tools, and playbooks to ramp quickly.
Coaching and feedback: Provide ongoing coaching and bring market signals back to leadership.
Systems and hygiene: Stand up reporting, pipeline discipline, and early forecasting.
Iteration: Refine ICPs, messaging, and channel strategy based on active deals.

Success milestones

Month 1: New reps set up, systems live, support in place.
Month 2: Active field work and pipeline creation in assigned channels.
Month 3+: Close initial deals, continue coaching, and formalize feedback loops.

Qualifications

Proven quota-carrying success in B2B or channel motions.
Experience building sales basics in an early or evolving GTM environment.
History of closing complex deals (government or enterprise a plus).
Able to coach while carrying an individual number.
Comfortable operating with ambiguity and iterating quickly.

Contract terms

Full-time hours during the engagement.
Initial 6-month contract; may convert to full-time employment, be extended, or be ended by Chegg Skills with 30 days’ notice.
Comp structure to balance stability and performance upside (to be finalized separately).

#LI-Remote

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
Certified Great Place to Work!: http://reviews.greatplacetowork.com/chegg
Chegg Corporate Career Page: https://jobs.chegg.com/
Chegg India: http://www.cheggindia.com/
Chegg Israel: http://insider.geektime.co.il/organizations/chegg
Chegg Skills: https://www.chegg.com/skills

Chegg out our culture and benefits!
https://www.chegg.com/about/working-at-chegg/benefits/
https://www.youtube.com/watch?v=YYHnkwiD7Oo
http://techblog.chegg.com/

Chegg is an equal opportunity employer
United States Remote: This is a remote position which may be performed anywhere in the United States.

Original Job Description

Sales Leader (Contract/Contingent Worker)

United States Remote

Full time

Job Description

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

Responsibilities

Revenue ownership: Carry a quota with clear channel ownership (government, enterprise, or partner accounts as assigned).
Deal execution: Prospect, run cycles, negotiate, and close.
Rep enablement: Make sure the two new hires have systems, tools, and playbooks to ramp quickly.
Coaching and feedback: Provide ongoing coaching and bring market signals back to leadership.
Systems and hygiene: Stand up reporting, pipeline discipline, and early forecasting.
Iteration: Refine ICPs, messaging, and channel strategy based on active deals.

Success milestones

Month 1: New reps set up, systems live, support in place.
Month 2: Active field work and pipeline creation in assigned channels.
Month 3+: Close initial deals, continue coaching, and formalize feedback loops.

Qualifications

Proven quota-carrying success in B2B or channel motions.
Experience building sales basics in an early or evolving GTM environment.
History of closing complex deals (government or enterprise a plus).
Able to coach while carrying an individual number.
Comfortable operating with ambiguity and iterating quickly.

Contract terms

Full-time hours during the engagement.
Initial 6-month contract; may convert to full-time employment, be extended, or be ended by Chegg Skills with 30 days’ notice.
Comp structure to balance stability and performance upside (to be finalized separately).

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Sales Leader (Contract/Contingent Worker)

Edtech.com's Summary

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