Senior Engineering Manager

Job DescriptionAI-Native Engineering LeadChegg • Austin, TX • New York, NY • Chicago, IL • Bay Area, CA • HybridThe RoleWe’re building a deeply AI-enabled product designed to give every college student an unfair advantage in the moments that matter most. This is Chegg’s single most transformative internal initiative: zero-to-one, live in market, and moving fast. The team is deliberately lean. Every person on it operates at a level well above their title.This is not a traditional engineering leadership role. We need someone who is genuinely AI-native — not AI-assisted — and who has the architectural instincts to keep our foundations sound as agents build faster on top of them. You will own the engineering craft end-to-end: deciding how we build, keeping the system honest, orchestrating AI tooling to multiply throughput, and growing the engineering capability of the team over time.You will report directly to the CTO and work closely with our Chief Architect, who brings 20+ years of experience and is one of the most effective AI-augmented engineers we have encountered. Your trajectory on this role is to eventually step into the Engineering leader position for this product and manage it’s lifecycle.You will collaborate closely with our product and business leaders, and a small team of engineers in the US and India. The pace is startup speed. The stakes are real.What you’ll doArchitecture & technical leadershipOwn the technical architecture of this product end-to-end — making the big calls on system design, data modeling, infrastructure, and how we build for scale from day oneSet and enforce engineering standards: code quality, security posture, observability, deployment practices, and incident responseAnticipate the hidden risks of building fast — identify architectural debt before it becomes a production problem, and make the tradeoffs explicitBuild systems that will keep working in production, not just systems that work in demosAI-native engineering & agent leverageUse AI coding agents not just as productivity aids but as a core part of how the team ships — structuring problems so agents can execute effectively, guiding them when they drift, and validating what they produceContinuously evolve the team’s AI workflows — you’re not looking for the best tool of today, you’re building the habit of always finding the best tool of tomorrowBuild and maintain the AI-native development loop: fast context-setting, high-quality prompting, deterministic validation, and tight human-in-the-loop reviewTrack what’s happening in the AI engineering tooling space and bring the best of it to the team before they askEngineering management & team growthManage and grow a lean team of engineers — right now that’s two talented ICs (one in the US, one in India); your job is to make them dramatically betterCreate clarity: clear priorities, clear technical direction, clear standards. The team should never wonder what “good” looks likeHire for AI-native fluency — you’ll help define what that means for this team and be a key voice in recruiting decisionsRun engineering with a product mindset: you understand that the goal isn’t working code, it’s outcomes for studentsProduct & outcome tastePartner closely with product and business leadership to translate product direction into technical strategy — you’re not a receiver of specs, you’re a co-author of themPush back when the technical approach doesn’t match the product ambition, and propose alternatives instead of just flagging problemsCare about the end user experience with the same intensity as you care about the codebase — you’ve shipped products that moved metrics, not just products that shippedKeep the team focused on the right problems. The most expensive mistake is building the wrong thing wellRequired Qualifications10+ years of software engineering experience, with at least 3 years in a technical leadership or engineering management role at a product companyProven architectural judgment — you’ve designed and scaled distributed systems and can speak to tradeoffs in data modeling, API design, caching, queuing, observability, and reliabilityDemonstrably AI-native: you use AI coding agents (Cursor, Claude, Copilot, or similar) as a primary part of your workflow, not as an occasional shortcut. You should have strong opinions on how to get real engineering throughput out of themProven engineering management experience — you’ve managed engineers, set technical direction, and held a team accountable to quality and velocityProduct mindset: you think in outcomes, not tickets. You have enough curiosity about users to form and test your own hypothesesComfort operating in ambiguity — you’re energized by zero-to-one environments, not paralyzed by themStrong written and verbal communication — you can explain architectural decisions clearly to both engineers and non-technical stakeholdersUS-based and located in or willing to commute to Austin TX, New York NY, Chicago IL, or the Bay Area CAPreferred QualificationsExperience building AI-powered or agent-based consumer products — you understand the unique design and reliability challenges of AI-driven user experiencesBackground in edtech, consumer internet, or products used at massive scale (millions of users)Experience building and managing globally distributed engineering teamsA strong point of view on how AI will reshape engineering organizations over the next 2–3 years — and a willingness to act on itHow we workThis product team runs like a startup inside Chegg. We’ve rebuilt our development process around AI-native workflows: tight loops, minimal ceremony, and agents doing more of the implementation so humans can focus on judgment, design, and quality. The team is small on purpose. Everyone operates above their title.This role is hybrid. We don’t require daily office presence, but you should be local to Austin, New York, Chicago, or the Bay Area and available for in-person collaboration during key sprints, architecture reviews, and team visits. Some weeks will be heads-down-in-the-office weeks, and a small amount of travel will be expected.You’ll report directly to the CTO and work closely with the Chief Architect and product and business leaders. You’ll be highly self-directed. No one will be managing your calendar or telling you what to build each morning. Success will be judged by the quality, reliability, and velocity of what the team ships — and by how much better the engineers around you become.The base salary pay range for this position is $180,000 to $285,000. 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: 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.About UsWhat is Chegg?An ‘always on’ digital learning platform.Chegg puts students first…Everything we build in this company is student-focused, making us the leading student-first connected learning platform. Chegg strives to improve the overall return on investment in education by helping students learn more in less time and at a lower cost. This is achieved by providing students a multitude of educational tools from affordable textbook rentals to Chegg Study which supplements their learning through 24/7 tutor access, step-by-step help with questions, and more.Chegg is a publicly-held company based in Santa Clara, California and trades on the NYSE under the symbol CHGG. #J-18808-Ljbffr