Sales Leader (Contract / Contingent Worker)

Sales Leader (Contract)

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

Qualifications

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).

Chegg Skills exists so students everywhere have a smarter, faster, more affordable way to student. We founded our business on providing affordable textbook rental options to address financial concerns for students. 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.