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Sales Director
Chegg, Inc.United States
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Espire Infolabs limitedLondon
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Über
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. Responsibilities
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 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.
Strategic Partnership
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.
Execution in Ambiguity
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.
Qualifications
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. Success Metrics
A clear, repeatable, and scalable sales process exists across the organization. The pipeline is healthy, predictable, and aligned to revenue goals. Sales velocity, conversion, and deal quality improve consistently. The sales team is coached, confident, and accountable. Marketing and Sales operate as true partners. Product and other teams have strong feedback loops from the market. Revenue becomes a function of system strength, not individual heroics. Benefits & Compensation
The On‑Target Earnings (OTE) range for this position is $205,000 to $300,000, inclusive of any sales incentive, sales commission, or other form of variable compensation. The actual pay will vary within this range based on geographic location, job type, professional experience, and other factors. Chegg offers a comprehensive benefits plan for eligible employees, including medical, dental, vision, life and supplemental life insurance, short‑ and long‑term disability, mental health support, parental leave, paid time off, paid holidays, 401(k) with matching contributions, Flexible Spending Account (FSA) and Health Savings Account (H.S.A.) options, an Employee Stock Purchase Plan, and other benefits. EEO Statement
Chegg is an equal opportunity employer.
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