Michelle Chen

AI Application Assistant – Smart Career Tools at Scale

Built and launched AI-powered features that increased job applications and platform engagement at scale

The Challenge

Job seekers often feel overwhelmed when applying to multiple roles. Many lack confidence in writing cover letters or optimizing resumes for visibility and clarity. This friction led to high drop-off rates and lost opportunities.
We saw a clear opportunity to build AI tools that could assist users in real time, helping them put their best foot forward and ultimately apply to more jobs.

My Role

As the lead product manager, I owned the full product cycle

  • Defined product scope, user flows, and success metrics
  • Collaborated with design, AI, and engineering teams
  • Engineered prompt structures for high-quality, adaptive LLM outputs
  • Launched iterative improvements through user feedback and data analysis

The Features

🔹 AI Cover Letter Generator

Automatically generates tailored cover letters based on the user’s resume and job description.

Key Functions:

  • Adapts tone, voice, and structure for different job types
  • Editable outputs so users can customize further
  • Fast, guided workflow integrated into job application flow
Generate a tailored cover letter directly from your resume and job details.
Customize tone and length to match your application style.
Instantly receive 1–3 AI-generated cover letters ready for review and use.

Impact
❤️ 80%+ satisfaction rate
📈 Adopted by over 50% of users
🙋‍♀️ Users applied to 4x more jobs

🔹 AI Resume Health Check

Analyzes resumes against 17 criteria to deliver actionable feedback across Style, Content, and Structure.

Key Functions:

  • Scoring system with instant suggestions and improvement tips
  • Highlights weak bullet points, missing impact metrics, and formatting issues
  • Encourages resume iteration by giving users clear revision guidance
The AI scans your resume to begin real-time analysis.
Get personalized feedback across 17 resume criteria with clear improvement tips.
eview suggestions and update your resume seamlessly in one place.

Impact
📈 Adopted by over 45% of users
🔁 Avg. user runs tool 2x/session
👍 80%+ satisfaction rate
🚀 Helped improve resume quality and increased job apply rate

💡 Why it worked

  • Smart, well-engineered prompts delivering useful, polished content
  • Feedback-driven iterations improved clarity and relevance over time
  • Frictionless UX that empowered users rather than replaced them
  • Seamless integration into Cake’s Resume Builder and platform

📊 Business Impact

Though free for users, these tools contributed directly to Cake’s B2B growth

  • More job applications = higher visibility for paid job listings
  • Improved resume quality = better talent pool for recruiters
  • Differentiated Cake from competing job boards with a value-driven AI layer

What I Learned & Takeaways

Shipping successful AI features isn’t just about technology — it’s about delivering value with empathy and intention.
This project reinforced how important it is to:

Design with user mindset and behavior in mind to reduce friction
Treat prompt engineering as a UX craft to ensure helpful, human-like outputs
Balance smart automation with transparency and user control to build trust

This project helped me bridge AI capability with practical product experience — and build features that people love to use.