Job Information
Chegg Inc. Sales Director in Olympia, Washington
ob Description
The Opportunity
Chegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning.
This role exists to build, scale, and lead the revenue engine that will define Chegg Skills' growth. We are looking for a Head of Sales who is more than a sales manager. This is a strategic, operational, and hands-on leader who can design systems, drive performance, coach teams, and close meaningful deals while navigating ambiguity.
What You'll Own
Revenue Strategy & Growth
Build and execute a clear sales strategy aligned to company growth goals
Identify opportunities across markets, verticals, and channels
Develop prospecting and closing strategies across:
Direct B2B
Channel partners
Government
Higher education
Workforce and enterprise buyers
- Translate market insight into revenue action
Sales Operations & Process Excellence
Design and implement scalable sales processes, playbooks, and operating rhythms
Own pipeline management, forecasting, and sales velocity metrics
Build systems that drive consistency, clarity, and performance
Establish clear performance standards and accountability frameworks
Create processes that connect Sales with Product, Marketing, Operations, Engineering, and Leadership
Team Leadership & Culture
Build and lead a high-performing, low-ego sales organization
Set the ton