Chegg is an educational powerhouse. Founded almost 20 years ago, Chegg has helped millions of students learn more effectively and get better grades. Chegg Skills is part of Chegg’s broader mission to help learners build practical, job-ready skills. Through career-focused programs and hands-on learning experiences, Chegg Skills supports adult learners as they develop real-world capabilities aligned to today’s workforce needs.
To deliver these programs at scale, Chegg Skills relies on strong internal systems that enable teams to design, build, and continuously improve learning experiences efficiently.
Why Chegg chose Retool
For teams focused on learning design and operational excellence, time and skills are precious and should be spent doing what they do best: improving educational outcomes, not building internal tools entirely from scratch.
Chegg Skills selected Retool as the foundation for its internal tooling because it enabled rapid prototyping and deployment of applications, while reducing the overhead typically associated with custom software development.
Retool also made it easier for engineers and non-engineers to collaborate on shared workflows, connecting internal tools directly to existing content and operational systems, while remaining flexible as processes evolved.
This balance of structure and adaptability allowed Chegg Skills teams to move quickly without sacrificing consistency or quality.
Why Chegg chose Bold Tech
By early 2024, Chegg Skills already had several Retool-based MVP tools in place. What they needed next was a partner who could help harden those prototypes, apply best practices, and support long-term scalability.
“We've had the pleasure of working with Bold Tech since the beginning of 2024 to augment our engineering team, particularly. They’ve been an exceptional partner that is collaborative, reliable, and deeply invested in our success.” - Alex Gonzalez, Senior Group Manager, Chegg
The Chegg Skills team partnered with Bold Tech with a clear objective: to consolidate internal tools into a cohesive experience that replaces manual and inefficient workflows with streamlined, automated processes.
Through collaborative discovery and system reviews, Bold Tech initially focused on strengthening existing applications. As the partnership matured, the teams began identifying opportunities to introduce AI in targeted, responsible ways that improved efficiency while keeping humans firmly in control.
Nearly two years later, the collaboration continues, with both teams iterating on and refining internal tools that support Chegg Skills’ evolving needs.
Our solutions: Scalable apps and AI-powered workflows
Over the course of the partnership, Bold Tech has worked closely with Chegg Skills to design and build internal Retool applications that are maintainable, scalable, and easy for teams to adopt.
These applications have, on average, saved 80 hours per month for all their internal teams. It has also allowed them to maintain high compliance standards that are required by external agencies.
Across these initiatives, two guiding principles emerged:
- Applying Retool best practices to reduce complexity and technical debt
- Using AI selectively to enhance efficiency and creativity, without over-engineering solutions that require precision and reliability
Here are a few examples of that work.
An end-to-end course development workflow
One of the largest initiatives supported the full lifecycle of course creation across multiple Chegg Skills teams. This internal workflow helps teams move from early research and validation through course structure design and content development.
Over multiple iterations, Bold Tech helped evolve this workflow to better support collaboration, consistency, and scale.
AI was introduced to assist with early-stage ideation by generating draft structures based on existing internal patterns and inputs. Rather than replacing expert judgment, this approach gave subject-matter experts a strong starting point, reducing time spent on blank-page work while preserving instructional intent.
The AI experience is embedded directly into the workflow, allowing users to refine outputs within clearly defined boundaries. This ensures AI supports existing educational standards and practices rather than introducing uncontrolled variation.
“[The Bold Tech] team has played a key role in launching major products like our Program Builder and improving the performance of tools like our AI Simulation platform.” - Alex Gonzalez, Senior Group Manager, Chegg
Interactive learning scenarios
Chegg Skills also uses interactive, AI-powered scenarios to help learners apply knowledge in realistic contexts. These guided conversations encourage active practice and reflection, reinforcing learning objectives through experiential engagement.
Bold Tech supported the creation of internal tools that allow course designers to define scenario structures, feedback styles, and evaluation criteria, ensuring consistency across learning experiences while still allowing flexibility in design.
These tools integrate seamlessly with Chegg Skills’ existing content systems, making it easy to create, update, and deploy scenarios as programs evolve.
AI-assisted quality review
Quality assurance was another area where AI could provide meaningful support. Previously, reviewers relied on manual checks to identify formatting issues, missing information, or inconsistencies, a process that was time-consuming and difficult to scale.
Bold Tech helped design an AI-assisted review workflow that performs an initial pass against clearly defined quality criteria, flags potential issues, and generates reviewer notes.
This approach allows human reviewers to focus on final judgment and instructional quality, while AI handles repetitive checks. The result is a faster, more consistent, and more scalable review process.
Knowing when not to use AI
Not every workflow benefits from AI. In some cases, Chegg Skills and Bold Tech found that deterministic, rules-based solutions were more reliable.
For example, an internal scheduling tool initially explored AI-driven logic, but this approach introduced inconsistencies. Replacing it with a straightforward algorithmic solution resulted in significantly improved reliability and predictability.
The lesson was simple: AI excels at exploration, synthesis, and creative support. When precision and correctness are required, traditional logic often remains the better choice.
The impact
Today, Chegg Skills operates a robust suite of internal Retool applications that are:
- Easy to maintain and evolve
- Closely aligned with real-world team workflows
- Significantly more efficient for course designers and operators
By combining Retool best practices with a pragmatic approach to AI, Bold Tech has helped Chegg Skills scale internal operations while preserving the quality and control that underpin effective learning experiences.
“Bold Tech has consistently delivered high-quality work, and we truly value the partnership.” - Alex Gonzalez, Senior Group Manager, Chegg
