ReApply & FitCheck
AI Career Intelligence Platform
Born from 800 job applications and 3 years of unemployment. A 9-engine AI platform that customizes every application—something even expensive career coaches don't do.
The founder's curse
After 25 years building companies, I found myself unemployed. Not for months. For years. 800 job applications. Almost no interviews.
The problem wasn't qualification. It was translation. My experience building teams, managing budgets, and solving complex problems was invisible because it wasn't presented in traditional employment language.
Professional career coaches are expensive—and even then, they rarely customize your materials for every single application. Resume writers charge hundreds for generic templates. 70% of resumes never get read by a human. The game is rigged against anyone whose background doesn't fit a standard box.
Who this affects
- + Founders re-entering employment
- + Career changers with non-linear paths
- + Parents returning to workforce
- + Veterans translating military experience
- + Anyone repeatedly rejected by ATS systems
9 AI engines in 6 weeks
Job Matching
Analyzes job requirements against resume to identify fit
Gap Analysis
Identifies skill mismatches and develops bridging strategies
ATS Optimization
Keyword analysis and formatting for automated screening
Company Research
Automated intelligence on mission, culture, and tech stack
Cultural Fit
Behavioral compatibility evaluation
Interview Prep
Strategic positioning and talking points
Resume Generation
Tailored resume content for specific opportunities
Cover Letter
Personalized cover letters aligned to job requirements
FitCheck Scoring
0-100 instant fit assessment on any job posting
Technical decisions
Credit-based pricing instead of subscriptions. When you're using metered AI APIs, subscription models create a unit economics nightmare. Credits align revenue with costs.
Structured outputs from every AI call. No parsing, no failures, no wasted calls. Every prompt is engineered to return exactly what's needed.
Aggressive caching with Redis. Company research, job analysis, and other expensive operations are cached intelligently to minimize redundant API calls.
Parallel orchestration across 9 engines. The coordination layer handles dependencies, failures, and race conditions so users see fast, reliable results.
Tech stack
Backend
AI/ML
Infrastructure
Payments
Extension
87% margins and product-led growth
87% gross margins on an AI product sounds like a ripoff. It's not. It's the result of solving the unit economics problem that kills most AI startups—and betting on product-led growth.
The strategy: build generous free usage into the product. If people actually use these tools, they promote themselves. Word of mouth from someone who landed a job beats any ad spend. It's a risk, but it aligns incentives—I only win if users win.
Those margins fund the free tier. They're not profit extraction—they're the runway for growth.
Solving the subscription problem
Everyone's sick of subscriptions. Monthly charges for tools you might not use that month. The guilt of paying for something sitting idle. The friction of yet another recurring bill.
Credits fix this. Buy what you need, use it when you need it, never worry about expiration. Pay for value delivered, not calendar months. It's fair to users and sustainable for the business.
More importantly, credits align revenue with costs. Every API call is metered. I know exactly what each feature costs to deliver. No surprises, no hoping the math works out.
FitCheck: 15-second fit scores
Job seekers waste hours applying to positions they're not qualified for. FitCheck shows a 0-100 fit score on any job posting in about 15 seconds.
- 1. Install extension, upload resume once
- 2. Browse LinkedIn, Indeed, any job board
- 3. Click FitCheck icon on any job posting
- 4. Get instant fit score with specific strengths and gaps
- 5. One-click to create full ReApply analysis
"ReApply exists to ensure that no qualified person goes unseen by opportunity."
The platform aims to un-rig the game by providing intelligence and tools that level the playing field for job seekers whose backgrounds don't fit standard boxes.
How it was built
Existing tools are either expensive (career coaches who don't customize for every application) or shallow (generic resume templates). After 800 job applications and watching qualified candidates get auto-rejected, I knew there had to be a way to deliver real intelligence at a price anyone could afford.
Aggressive prompt engineering, structured outputs to eliminate failed calls, intelligent caching with Redis, and a credit-based pricing model that aligns costs with revenue. Every AI call is optimized to extract maximum value.
Job seekers browse job boards. They need fit intelligence where they already are, not in a separate app. The extension delivers a fit score in 15 seconds on any job page, then one-click integration to ReApply for deeper analysis.
Coordinating 9 AI engines to work in parallel without race conditions, failed calls cascading, or duplicate work. The orchestration layer took more engineering than any individual engine.
See it live
Have a platform idea?
I build AI-powered platforms for founders. Let's talk about what you're trying to create.
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