Sales Director

Chegg Inc.•Remote (CA), CA

79d•$205,000 - $300,000

About The Position

Chegg Skills is building the next chapter of Chegg, operating 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.

Requirements

Proven track record of building and scaling sales organizations
Deeply data-driven and detail-oriented
Experience designing sales processes, playbooks, and operating models from the ground up
Comfortable in strategy conversations and live deals
Understand GTM across multiple channels and buyer types
Skilled at coaching, training, and elevating sales talent
Respected as both a leader and a partner
Thrive in fast-moving, ambiguous environments
Scrappy, resourceful, and execution-focused

Responsibilities

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
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
Build and lead a high-performing, low-ego sales organization
Set the tone for culture, execution, and accountability
Lead daily standups, pipeline reviews, and deal strategy sessions
Facilitate deal swarms for high-value opportunities
Step into deals when needed and coach in real time
Develop talent through ongoing training, coaching, and performance management
Partner closely with the Head of Marketing to align demand generation and revenue execution
Serve as a trusted consultant to leaders across the organization
Translate business priorities into clear sales motions and outcomes
Bring a revenue perspective to company-wide decisions
Operate effectively in an environment that combines startup speed with enterprise complexity
Build structure where needed without slowing momentum
Make smart decisions with imperfect information and adjust quickly
Balance long-term strategy with immediate execution