Job DescriptionThe OpportunityChegg Skills is building the next chapter of Chegg. We operate at the intersection of workforce upskilling, career mobility, and outcomes-driven learning. While we benefit from Chegg's scale and credibility, we are intentionally distinct from "big Chegg" and its legacy.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 OwnRevenue 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 B2BChannel partnersGovernmentHigher educationWorkforce and enterprise buyers Translate market insight into revenue actionSales 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 LeadershipTeam 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 managementStrategic 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 decisionsExecution 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 executionWho You AreYou are not just a sales leader. You are a builder and architect of revenue systems. 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-focusedWhat Great Looks Like in This Role 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 heroicsWhy This Role MattersThis is a defining role in building Chegg Skills' growth engine. You will not inherit a finished system. You will design it, build it, and scale it.If you are looking for comfort, this is not it.If you are looking for ownership, influence, and the chance to build something meaningful, this is.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 comp
