Chegg Inc.

Role Description At Chegg, we’re on a mission to deliver an unprecedented return on a student’s time and money. Our programs deliver exceptional outcomes at market-leading prices by offering seamless experiences for students from the day they enroll at Chegg Skills until the day they graduate. We are looking for a Digital Marketing Industry Coach to join our team and support students on their educational journey. This individual will provide high-quality coaching to Chegg Skills students by acting as a coach and thought partner while fostering confidence as they approach the end of their program and prepare to apply their skills in the professional world. In this role, you will serve as a trusted coach, helping students apply new skills with confidence to their current or future role. Through personalized coaching, you will provide industry insights, guidance on workplace dynamics, and strategies for effectively integrating their learning into real-world scenarios. By fostering a supportive and encouraging environment, you will help students build self-assurance, refine their professional presence, and adapt to evolving industry expectations. This is an ideal opportunity for someone passionate about building relationships and helping students succeed. Your role will be instrumental in providing thoughtful feedback, facilitating discussions that deepen industry knowledge, and ensuring students feel empowered to advance in their careers with clarity and confidence. Responsibilities - Conduct one-on-one online video sessions with students to discuss career goals, challenges, and strategies for success in tech-focused roles. - Act as a sounding board for students, fostering a supportive relationship that motivates students to pursue their goals with confidence. - Coach students on professional skills, including communication, networking, problem-solving, adaptability, and professional etiquette. - Share industry insights and real-world examples to enhance student application of skills. - Provide actionable feedback on student readiness and areas for improvement. - Document session content to ensure consistent support across teams. - Leave a student-first and empathetic impression with all learners. Qualifications - Minimum of 4 years experience in Digital Marketing. - Prior experience in mentorship, coaching, or professional development. - Strong ability to connect with students and provide clear, actionable guidance. - Excellent interpersonal skills, including a developed sense of empathy and understanding. - Demonstrated ability to motivate and support individuals from diverse backgrounds and skill levels. - Familiarity with hiring trends, industry demands, and essential competencies in tech-heavy fields. - Adaptable to a fast-paced work environment. - Must have a reliable, high-speed internet connection and webcam. - Knowledge of Digital Marketing strategies, campaigns, KPIs, buyer personas, empathy maps, market branding, style guides, creative briefs, content marketing, email marketing, social media marketing, paid social, SEO, paid search, analytics. Requirements - The base salary pay range for this position is USD 38.00 per hour. Benefits - 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. - Employee Stock Purchase Plan. - Other benefits found at: Chegg Benefits .

Role Description We are looking for a Senior Engineer to join our AI team at the intersection of evaluation science, post-training, and foundation model development. You will own our end-to-end eval and benchmarking infrastructure — the critical feedback loop that drives every major model improvement — while contributing hands-on to post-training pipelines for industry-specific vertical foundation models. This role is ideal for someone who has worked directly inside an LLM lab and understands what rigorous evaluation looks like at scale: - Designing the taxonomy of skills being measured - Identifying failure modes - Engineering synthetic data to close capability gaps - Translating eval signals into actionable training decisions Qualifications - 5+ years of ML/AI engineering experience, with at least 2–3 years focused on large language models - Direct, hands-on experience at an LLM lab, AI research organization, or equivalent frontier AI team - Familiarity with the full model lifecycle: pre-training data, post-training alignment, eval, and production deployment - Deep practical expertise in post-training methods: SFT, RLHF, RLAIF, DPO, PPO - Experience with reward modeling, preference data curation, and quality control for alignment pipelines - Demonstrated experience designing LLM evaluation frameworks beyond standard benchmarks - Hands-on experience building synthetic data generation pipelines to address specific model capability gaps - Proven track record of comparative benchmarking across leading foundation models - Experience training or fine-tuning vertical/industry-specific foundation models - Strong software engineering fundamentals: Python, PyTorch or JAX, distributed training Requirements - Lead or directly contribute to SFT, RLHF, RLAIF, and DPO training runs on industry-specific vertical foundation models - Curate and engineer high-quality instruction-tuning and preference datasets for domain adaptation - Define data quality criteria, rejection sampling strategies, and deduplication pipelines for SFT corpora - Design preference pair construction methodologies and reward model training setups - Implement and experiment with alignment techniques including reward modelling and constitutional/RLAIF approaches - Run ablation studies and controlled experiments to attribute model behaviour changes - Contribute to continual pre-training and domain-adaptive fine-tuning pipelines - Build scalable eval pipelines that run automatically on every training checkpoint - Maintain model cards, eval leaderboards, and internal dashboards - Ensure reproducibility through rigorous experiment tracking Benefits - Flexible work environment - Health and wellness programs - Professional development opportunities - Competitive salary and equity options - Generous vacation policy Company Description 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 providing 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 study.

Role Description - Conduct mentoring sessions and live lessons on assigned digital marketing topics. - Maintain a QA score of 80% or above in all student interactions and deliverables. - Provide on-demand academic support, including tailored guidance and video explanations, to help students clarify concepts and apply them to their assignments. - Participate in Q&A sessions to reinforce student understanding and application of concepts. - Contribute to discussions and share relevant resources within the student community to keep learners engaged and informed. - Review and grade student assignments according to defined guidelines and benchmarks. - Deliver clear, actionable feedback to help students improve their submissions. - Check grading work to ensure accuracy and compliance with updated processes. - Review content from approved sources to confirm accuracy, relevance, and alignment with course objectives. - Share observations on skill gaps or process challenges to support ongoing improvements. - Assist in onboarding activities for new team members during their initial training period. - Provide day-to-day support to ensure grading and feedback maintain consistent quality. - Suggest curriculum updates or additions based on learner needs and market trends. - Share ideas for new course topics aligned with current digital marketing practices. - Recommend refinements to process documents for better efficiency and clarity. - Research and share tools, resources, and emerging technologies to enhance subject delivery. - Monitor grading volumes to help identify potential workload adjustments. - Contribute to preparing performance summaries for grading activities. - Review graded checkpoints, Slack discussions, and on-demand support sessions to ensure quality compliance. - Suggest improvements based on analysis of content quality and learner interactions. Qualifications - Minimum 3 years of professional experience in digital marketing or a related field (EdTech experience preferred). - Strong communication skills to deliver live lessons and interact with a U.S.-based audience. - Proficiency in Zoom and other online learning platforms. - Solid understanding of digital marketing concepts, tools, and best practices, supported by a relevant degree. - Familiarity with subject-specific software and tools such as Google Analytics, Google Ads, Meta Business Suite, SEO tools, email marketing platforms, and content management systems. Benefits - Affordable textbook rental options to address financial concerns for students. - Support for students beyond their college experience through various offerings like Chegg Study, Chegg Math, Chegg Writing, Chegg Internships, and Chegg Skills. - Modernized learning experience to lower financial concerns for students. Company Description Chegg is an equal opportunity employer.

Role Description The Facilitator – Data Analytics plays a critical role in delivering high-quality academic support and learning experiences to students enrolled in the Data Analytics program. The Facilitator is responsible for: - Conducting live instructional sessions - Supporting students through on-demand tutoring and video explanations - Performing quality assurance reviews - Contributing to learner engagement initiatives This role requires strong analytical expertise, structured problem-solving ability, and the capability to explain complex data concepts clearly to beginner and intermediate learners. The Facilitator will collaborate closely with mentors and academic teams to: - Improve instructional delivery quality - Support newly onboarded experts (MNEs) - Contribute to curriculum enhancement aligned with evolving industry expectations Candidates with strong academic backgrounds and research orientation—particularly PhD holders or candidates currently pursuing a PhD in Data Science, Statistics, Mathematics, Computer Science, or related domains—will be given preference. Qualifications - Minimum 3+ years of relevant industry and/or teaching experience in Data Analytics or related domains - Strong hands-on experience with modern analytics workflows and business data interpretation - Preference for candidates holding a PhD or pursuing a PhD in Data Science, Statistics, Mathematics, Computer Science, or related disciplines - Bachelor’s or Master’s degree in Data Analytics, Statistics, Mathematics, Computer Science, Engineering, or related domains preferred - Prior experience in EdTech or online instruction is an added advantage - Strong communication skills with the ability to teach US-based learners - Experience conducting sessions using Zoom or similar virtual learning platforms - Strong organizational and time-management skills - Ability to explain complex analytical topics clearly without unnecessary jargon - Strong written and verbal English proficiency - Willingness to work rotational shifts and week-offs based on business requirements - Ability to mentor junior experts and contribute to academic quality improvement initiatives Requirements - Perform all core academic support activities including: - Live Lessons - Weekly Video Tutoring - On-Demand Tutoring Support - QA Review - Maintain a minimum QA score of 80% or above across all assigned activities - Deliver high-quality responses aligned with academic standards during live support interactions - Review mentor session content based on updated internal guidelines - Provide structured feedback on externally sourced academic content across all difficulty levels - Support students through on-demand video explanations - Conduct interactive Q&A sessions to enhance conceptual clarity - Participate in community engagement initiatives to support learner success - Identify learner knowledge gaps and escalate insights to Leads - Train and mentor MNEs during their first 90 days of onboarding - Provide continuous process support to MNEs in their day-to-day academic activities - Collaborate with mentors and academic teams to strengthen delivery quality - Suggest improvements to activity guidelines, internal processes, and learning workflows - Contribute recommendations for curriculum updates and new course additions aligned with market demand - Monitor incoming academic workload and recommend shift redistribution when required - Prepare contribution reports on SME academic effectiveness and live support engagement quality - Curate emerging analytics tools, datasets, and workflows relevant to Data Analytics programs Benefits - Support curriculum alignment with evolving data analytics industry expectations and hiring trends - Assist in identifying opportunities to improve learner experience across analytics learning pathways Company Description Chegg is an equal opportunity employer.

Role Description As Chegg Skills engineers, our software empowers students to move from “learning” to “earning”. We build the apps and systems that help students make life-changing career changes into high-growth job opportunities. We pride ourselves on our ability to provide accessible education to motivated career switchers. Together we build the tech that helps them reach mastery and success. In this role, you will play a leading role in a fully remote team of diverse, motivated engineers that is changing what education looks like. We serve an audience of thousands of students and educators every year. Your contributions will shape the way these students learn, helping them succeed in life. Chegg Skills is a new and growing division of Chegg focusing on post-collegiate demographics. We are growing the engineering team to help support our continued business expansion as more students take the next step in their careers with Chegg. Join us and help scale engineering to power our next phase of growth! We expect that most qualified candidates will have at least 6 years of professional software development experience building user-facing web applications. - Within 1 month, you will: - Work with an onboarding buddy to push commits in your first week. - Use our documentation to learn the microservices architecture. - Start familiarizing yourself with our React.js, Next.js, and Node.js codebases and begin contributing. - Use code reviews and pairing with peers to raise code quality. - Deploy changes confidently with solid test coverage through our robust CI/CD pipeline. - Participate in sprint planning and retrospective meetings. - Get to know your remote peers and stakeholders over video calls. - Identify pain points in the team’s process and codebases with fresh eyes, and share ideas from past experiences. - Within 3 months, you will: - Collaborate with developers, product managers, and stakeholders to identify product opportunities. - Demonstrate expertise in using JS/React to quickly iterate toward product goals. - Employ industry best practices in your work, and share those practices with your peers. - Work across the stack and multiple applications to create user experiences that support our students’ learning. - Standardize our application data access by contributing to a new GraphQL layer. - Improve observability across the system through standardized logging, metrics, and dashboards. - Maximize your impact in an environment that strives for high focus and infrequent engineering interruptions. - Invest in a culture of accountability by holding yourself and your peers to high standards. - Receive regular performance feedback from your manager and peers. - Within 6 months, you will: - Influence the roadmap and product development of Chegg Skills systems. - Expand your knowledge and influence by rotating across project pods and working in new codebases and product areas. - Lead research and architecture initiatives to support Chegg Skills’ rapid growth. - Hone your skills with accessibility training and make accessibility part of your “definition of done”. - Standardize and document operating procedures. - Invest in junior developers through mentoring relationships. - Develop a career growth plan and goals with your manager. Qualifications - At least 6 years of professional software development experience. - Experience building user-facing web applications. Requirements - Proficiency in React.js, Next.js, and Node.js. - Experience with microservices architecture. - Ability to work collaboratively in a remote team. - Strong understanding of CI/CD pipelines. Benefits - Flexible remote work environment. - Opportunities for career growth and development. - Access to mentorship and training programs. Company Description Chegg exists to support students in their educational journey by providing affordable textbook rental options and a variety of services to enhance their learning experience. - Chegg Study - Chegg Math - Chegg Writing - Chegg Internships - Chegg Skills We aim to lower financial concerns for students by modernizing their learning experience.

Role Description This is a rare opportunity to build a new capability from the ground up. You will work on high-visibility problems that sit at the intersection of data science, strategy, business performance, and AI transformation. You will partner directly with leadership, shape how the company measures itself, and build the operating intelligence that helps Busuu make better decisions, faster. - Build a new organisational intelligence capability in a company actively reshaping itself around AI. - Work on problems with direct visibility to the General Manager, leadership team, and cross-functional heads. - Design cutting-edge measurement systems, decision frameworks, and intelligence layers — not just dashboards. - Operate across B2C, B2B, Product, Commercial, and AI initiatives, with broad influence on how the company runs. - Combine deep analytical thinking with real business impact in a role that is strategic, hands-on, and highly visible. We are hiring a Staff Data Scientist to lead Organisational Intelligence within Decision Intelligence. The mission of this role is to help Busuu understand itself as a system: how performance is evolving, where transformation is working or failing, how teams should interpret signals across the business, and what leadership should do next. - Design the measurement architecture, synthesis, and business learning loops that connect data to decisions at company level. - Own the analytical foundation behind monthly and quarterly business reviews. - Define how transformation is measured, establish trusted business metric definitions, and help turn AI governance into an operating reality. Qualifications - 8+ years of experience in data science, analytics, business intelligence, strategy, consulting, or a similar function in a scaled digital, SaaS, consumer tech, subscription, or EdTech business. - Strong experience translating analysis into business decisions, preferably with exposure to executive or leadership-level reporting. - Experience designing performance frameworks, KPI systems, company scorecards, business review processes, or equivalent decision-support systems. - Strong SQL skills and confidence working directly with complex datasets. - Ability to move fluidly between hands-on analytical work and high-level executive communication. - Experience influencing senior stakeholders across functions such as Product, Finance, Commercial, Marketing, Operations, Engineering, or Data. - Strong commercial judgment, including understanding of metrics such as bookings, retention, NRR, funnel performance, LTV:CAC, and unit economics. Requirements - Experience across both B2C subscription and B2B SaaS environments. - Experience in AI, transformation, operating model change, or measurement of organisational effectiveness. - Experience defining semantic logic, metric governance, or business logic in partnership with analytics engineering or data engineering teams. - Experience contributing to board-level, leadership-level, or annual operating narratives. - Python or similar analytical tooling for data exploration, prototyping, and scalable analysis. Benefits - Significant autonomy and broad exposure. - Opportunity to shape a capability that matters to the future of Busuu. Company Description Joining Busuu means being part of one of the top EdTech companies in the world, a multiple award-winner recognised for its innovation and impact in language learning. Busuu’s vision is to empower people through languages. We are the world’s largest online community for language learning, with 120+ million registered users.

Role Description At Chegg Skills, we’re on a mission to deliver an unprecedented return on students’ time and money. Our programs deliver exceptional outcomes at market-leading prices by providing a seamless experience from enrollment through graduation. We are looking for a Student Success Coach to join our dynamic team. In this high-touch, video coaching role , you will guide, motivate, and provide personalized support for a diverse group of learners through live video sessions, helping them build strong habits, set meaningful goals, and overcome obstacles. Your work will center on reflective coaching that drives accountability, fosters growth, and empowers learners to take ownership of their learning journeys. Success in this role is measured by your students' progress, retention, and graduation rates. This role is ideal for coaches who thrive in live, interactive sessions, can sustain energy across multiple personalized interactions per week, and are committed to driving meaningful growth for each learner. Responsibilities - Guide, motivate, and coach learners with diverse needs, backgrounds, and experiences through relationship-based, live video coaching. - Deliver high-touch, live video coaching sessions (20–30 minutes each) with up to 40–50 sessions per week, ensuring each interaction is personalized to the learner’s goals, challenges, and circumstances. - Prepare sessions by reviewing learner history, progress, and behavioral data to guide reflective, targeted coaching conversations. - Document coaching interactions and learner progress in CRM systems to maintain continuity and inform future sessions. - Conduct follow-up communications to reinforce insights, clarify next steps, and sustain accountability between sessions. - Drive accountability, motivation, and skill-building through thoughtful questioning, reflection, and goal-setting, helping learners overcome obstacles and take ownership of their learning journey. - Collaborate with Enrollment Managers, Outreach Coordinators, and the enablement team to address learner needs and ensure a smooth, supportive learner experience. - Participate in virtual workshops, group coaching sessions, and office hours as needed to reinforce learning and engagement. - Provide feedback on coaching processes, tools, and strategies to optimize learner outcomes. - Partner with the Enablement team to test and refine coaching strategies and contribute to the ongoing development of the coaching toolkit. Qualifications - 3–5+ years of experience in coaching, student success, or related learner-facing roles. - Strong passion for live, interactive coaching, with the ability to engage learners across multiple sessions per week. - Comfort managing a high-volume coaching schedule, while delivering quality, individualized support. - Ability to guide learners toward self-discovery and ownership, empowering them to set goals, build habits, and overcome challenges. - Excellent verbal and written communication skills, with strong empathy and clarity. - Demonstrated ability to motivate learners, including reconnecting them to their goals and “why.” - Understanding of adult learning principles (andragogy); teaching or counseling experience is a plus. - Ability to manage competing priorities in a fast-paced, evolving environment. - Strong work ethic and commitment to learner outcomes. - Availability 9 am-5 pm PST. - Experience with Planhat, Zendesk, or similar CRM and support tools is a plus. Requirements - The base salary pay range for this position is between USD 64800 to USD 85000. 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. Benefits - 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 - Employee Stock Purchase Plan - Other benefits found at: Chegg Benefits Company Description 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 providing 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 study.

Role Description At Chegg, we’re on a mission to deliver an unprecedented return on a student’s time and money. Our programs deliver exceptional outcomes at market-leading prices by offering seamless experiences for students from the day they enroll at Chegg Skills until the day they graduate. We are looking for a Student Success Outreach Coordinator to join our team and support students in their educational journey. This individual will manage a high-volume caseload of students, engage with them through various communication channels, and ensure they remain on track to complete their programs and acquire the skills they need to reach their goals. In this role, you will: - Proactively engage students, helping to convert trial-period students into confirmed enrollments. - Drive sustained learner engagement throughout their program. - Use strong communication skills and problem-solving abilities to re-engage students who may have fallen behind. - Guide students through program milestones and connect them with the right internal resources. - Contribute to optimizing outreach strategies and workflows. - Collaborate with team members to ensure students receive the support they need to succeed. This is an ideal opportunity for someone who is passionate about student success, enjoys working in a fast-paced environment, and is motivated to meet and exceed both individual and team targets. Responsibilities - Manage a high-volume caseload of students, providing proactive and personalized support through text, email, video chat, and other communication channels. - Execute a repetitive and detailed workflow focused on contacting a high volume of learners daily to hit enrollment, retention, and graduation targets. - Leverage CRM tooling and established playbooks to monitor, document, and report on individual and group-wide learner progress and performance. - Outreach to 250+ students per week and make informed decisions on follow-up communications. - Utilize discovery questions and active listening skills to uncover and understand learner needs. - Leave a student-first and empathetic impression with all learners. - Meet or exceed assigned sales quota by executing the sales cycle and maintaining assigned learner caseload. - Review the optimization and impact of outreach performance to achieve and/or exceed targets. - Work closely with the Enrollment Manager, Success Coaches, and enablement team to address learner needs. - Provide feedback on outreach processes, team tooling, and workflow to help optimize day-to-day operations. - Partner with the enablement team to test new outreach tactics, creative messaging, and communication automation triggers. - Develop knowledge on each of Chegg Skills’s programs and potential sticking points. Qualifications - 1-2+ years of sales, business development, customer success, or learner engagement experience, preferably in a high growth SaaS or technology environment. - Ability to provide high quality support to a high volume of learners. - Outstanding communication skills, both written and verbal. - Experience crafting outbound communications, measuring results, and optimizing efforts. - Exceptional ability to reignite a learner or customer’s “why” or excitement about the product. - Excellent prioritization and task execution. - Adaptable and thrive in ambiguous or rapidly changing situations. - A strong work ethic and drive to meet and exceed target learner outcomes. - Experience with Planhat and Zendesk a plus. - Availability to work during PT hours of 9AM-5PM a plus. Requirements - The base salary pay range for this position is $57,350 to $80,000. - Actual pay will vary within this range based on geographic location, job type, professional experience, and other factors. Company Description 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 providing 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 study.

Role Description We are looking for an experienced Full Stack Developer who can build and manage end-to-end SaaS applications similar to scheduling and productivity platforms like Calendly. The ideal candidate should be capable of independently handling architecture, front-end development, back-end systems, integrations, deployment, and scaling of modern web applications. You will work on internal products focused on scheduling, automation, user management, notifications, integrations, and workflow optimization. - Design and develop scalable SaaS applications from scratch - Build scheduling, booking, and calendar management systems - Develop responsive and modern front-end interfaces - Create secure and scalable backend APIs and services - Integrate third-party platforms such as: - Google Calendar - Outlook Calendar - Zoom - Stripe - Email and notification systems - Implement authentication, role management, and permissions - Manage cloud infrastructure and deployments - Optimize applications for performance and scalability - Collaborate with product and operations teams to define features - Maintain code quality, testing, and documentation Qualifications - Front-End: - React.js / Next.js - TypeScript & JavaScript - HTML5, CSS3, Tailwind CSS - Responsive and mobile-first UI development - Back-End: - Node.js / Express.js - REST APIs & Webhooks - Authentication systems (JWT, OAuth, SSO) - Database: - PostgreSQL / MySQL - MongoDB (optional) - Cloud & DevOps: - AWS / GCP / Azure - Docker - CI/CD pipelines - Git & GitHub workflows - Additional Technical Skills: - Real-time systems and notifications - Scheduling logic and timezone handling - API integrations - SaaS architecture understanding - Performance optimization Requirements - 3+ years of full stack development experience - Proven experience delivering production-ready applications independently What We’re Looking For We are looking for someone who can take ownership of complete product development and contribute beyond coding — including architecture decisions, scalability planning, integrations, and deployment. The ideal candidate should be proactive, product-minded, and comfortable building modern SaaS applications end-to-end. Company Description 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.

Role Description 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 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 - You 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-focused Requirements - 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 - 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 - Employee Stock Purchase Plan