Sales Leader (Contract/Contingent Worker)

Chegg; India; Remote; INR 15,00,000 - 25,00,000; Full time

Job summary

A leading education solutions provider is seeking a Sales Leader to drive revenue growth in B2B partnerships. You will be responsible for closing deals and mentoring new hires while refining sales strategies. Ideal candidates have a proven quota-carrying record and experience in complex deal closures. This is a full-time contract position, potentially leading to a permanent role.

Qualifications

• Proven success in achieving quotas.
• Experience in an evolving GTM environment.
• Ability to close complex deals.

Responsibilities

• Own revenue with assigned channel accounts.
• Prospect, negotiate, and close deals.
• Enable new reps with necessary tools.

Skills

Quota-carrying success

Experience in B2B sales

Coaching ability

Comfortable with ambiguity

Job description

Overview

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 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).

Chegg is an equal opportunity employer.

United States Remote: This is a remote position which may be performed anywhere in the United States.