Senior Engineering Manager

About the Team

Chegg is on a mission to give every college student an unfair advantage in the moments that matter most. We are building a deeply AI-enabled product designed to modernize the learning experience and lower financial concerns for students worldwide. This initiative is Chegg's single most transformative internal project: a zero-to-one effort that is already live in the market and moving at startup speed.

The team is deliberately lean, with every person operating at a level well above their title. We have rebuilt our development process around AI-native workflows, utilizing tight loops and minimal ceremony so that AI agents handle more implementation while humans focus on judgment, design, and quality. You will report directly to the CTO and collaborate closely with a Chief Architect who brings over 20 years of experience as one of the most effective AI-augmented engineers we have encountered.

About the Role

This is not a traditional engineering leadership role. We need someone who is genuinely AI-native—not just AI-assisted—and who possesses 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.

Your trajectory in this role is to eventually step into the Engineering Leader position for this product and manage its lifecycle. You will partner with product and business leaders to translate direction into technical strategy, acting as a co-author of specs rather than just a receiver. The stakes are real, and the pace is fast; you will be highly self-directed with no one managing your calendar, judged instead by the quality, reliability, and velocity of what the team ships.

Hiring Process

We are looking for candidates who are energized by ambiguity and zero-to-one environments. The interview process is designed to assess your architectural judgment, AI-native fluency, and product mindset. While specific steps are not detailed here, we prioritize candidates who can demonstrate how they use AI coding agents as a primary part of their workflow to drive real engineering throughput.

How We Work

This role is hybrid. While we do not require daily office presence, you must 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, and a small amount of travel will be expected.

Our Culture & Mission

Students are working harder than ever to stabilize their future. Nearly 3 out of 4 students are working to support themselves through college, and 1 in 3 feel pressure to spend more than they can afford. We exist so students everywhere have a smarter, faster, more affordable way to learn. From our origins in affordable textbook rentals to our current suite of offerings like Chegg Study, Writing, and Skills, we are dedicated to supporting students beyond their college experience.

Equal Opportunity

Chegg is an equal opportunity employer. We consider qualified applicants regardless of background, identity, or experience.