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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.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 & GrowthBuild and execute a clear sales strategy aligned to company growth goalsIdentify opportunities across markets, verticals, and channelsDevelop prospecting and closing strategies across:Direct B2BChannel partnersGovernmentHigher educationWorkforce and enterprise buyersTranslate market insight into revenue actionSales Operations & Process ExcellenceDesign and implement scalable sales processes, playbooks, and operating rhythmsOwn pipeline management, forecasting, and sales velocity metricsBuild systems that drive consistency, clarity, and performanceEstablish clear performance standards and accountability frameworksCreate processes that connect Sales with Product, Marketing, Operations, Engineering, and LeadershipTeam Leadership & CultureBuild and lead a high-performing, low-ego sales organizationSet the tone for culture, execution, and accountabilityLead daily standups, pipeline reviews, and deal strategy sessionsFacilitate deal swarms for high-value opportunitiesStep into deals when needed and coach in real timeDevelop talent through ongoing training, coaching, and performance managementStrategic PartnershipPartner closely with the Head of Marketing to align demand generation and revenue executionServe as a trusted consultant to leaders across the organizationTranslate business priorities into clear sales motions and outcomesBring a revenue perspective to company-wide decisionsExecution in AmbiguityOperate effectively in an environment that combines startup speed with enterprise complexityBuild structure where needed without slowing momentumMake smart decisions with imperfect information and adjust quicklyBalance 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 organizationsDeeply data-driven and detail-orientedExperience designing sales processes, playbooks, and operating models from the ground upComfortable in strategy conversations and live dealsUnderstand GTM across multiple channels and buyer typesSkilled at coaching, training, and elevating sales talentRespected as both a leader and a partnerThrive in fast-moving, ambiguous environmentsScrappy, resourceful, and execution-focusedWhat Great Looks Like in This RoleA clear, repeatable, and scalable sales process exists across the organizationThe pipeline is healthy, predictable, and aligned to revenue goalsSales velocity, conversion, and deal quality improve consistentlyThe sales team is coached, confident, and accountableMarketing and Sales operate as true partnersProduct and other teams have strong feedback loops from the marketRevenue 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 compensation. Although this range represents the full range for the position, the actual pay will vary within this range based on geographic location, job type, professional experience, and other factors. In addition, 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 found at: https://www.chegg.com/about/working-at-chegg/benefits/.Why do we exist?Students are working harder than ever before to stabilize their future. Our recent research study called State of the Student shows that nearly 3 out of 4 students are working to support themselves through college and 1 in 3 students feel pressure to spend more than they can afford. We founded our business on provided affordable textbook rental options to address these issues. Since then, we've expanded our offerings to supplement many facets of higher educational learning through Chegg Study, Chegg Math, Chegg Writing, Chegg Internships, Chegg Skills, and more to support students beyond their college experience. These offerings lower financial concerns for students by modernizing their learning experience. We exist so students everywhere have a smarter, faster, more affordable way to student.Video ShortsLife at Chegg: http://youtu.be/Fwf90zgaOLAChegg Corporate Career Page: https://jobs.chegg.com/Chegg India: http://www.cheggindia.com/Chegg Israel: http://www.chegg.com/about/working-at-chegg/israel/Chegg Skills: https://www.chegg.com/skillsChegg out our culture and benefits!http://www.chegg.com/about/working-at-chegg/benefits/Chegg is an equal opportunity employerApply here: https://www.aplitrak.com/?adid=YmJnZW5lcmljLjM2NTU1LjEzMjUzQGNoZWdnY29tcC5hcGxpdHJhay5jb20