Work
TailorFit: what I built while trying to get hired myself
I was deep in my own job search, staring down hundreds of applications, doing what most people do: reusing one generic resume because tailoring each one by hand is too much work. So I built a workflow with Claude to speed it up. It grew into a full platform for tracking both the applications and the career story behind them.
Where it started
The workflow came before the product. Mid search, I started dumping my whole work history into Claude as word vomit: half-remembered projects, metrics I had to go dig up, context that only made sense in my own head. Claude and a couple of other AI agents would parse that into something usable, then tailor a resume and write a specific, custom cover letter for whatever role I was looking at next. It worked, but it lived entirely in scattered chats and local files, and every new application meant re-explaining myself from zero. TailorFit is that workflow rebuilt as an actual product: the brain dump becomes a structured Background once, and every resume, cover letter, and job analysis after that draws from it instead of starting over.
Tracking the search
| Company / Role | Stage | Tags | Fill |
|---|---|---|---|
| Vertex RoboticsDesign Systems Lead | Screening | No JD | 25% |
| Lumen HealthSenior Product Designer | Offer | No JD | 25% |
| Cascade RoboticsPrincipal Designer | Rejected | No JD | 25% |
| Beacon AnalyticsSenior Product Designer | Interview | No JD | 75% |
Recreated from the real product (generic demo data). Every application carries a completeness score, plus the stage pills, tags, and filters shown in the real tracker.
What the AI actually reads
Must-haves
- 6+ years product design experience
- Expertise with complex B2B data products
Highlights
Remote-friendly arrangement, B2B data product expertise is a specialized, high-demand skill set.
Watch out
No explicit compensation range, vague on team structure and reporting.
Question to ask
What's the current design team structure, and who would I report to?
Recreated from the real product (generic demo data). Tai reads the job listing itself and pulls out must-haves, red flags, and market context, not just keyword matches.
Making the pitch, not just the app
A tool nobody can find is a tool nobody uses, so the marketing site got the same attention as the product. The homepage leads with the actual problem instead of a generic AI pitch, and pricing is built around credits instead of a flat per-generation cap, so an occasional job seeker and someone running a hundred applications both pay for what they actually use.
Your background qualifies you for more than you're applying for.
Most searches are too narrow and too hard to keep track of. TailorFit builds a real professional profile from your experience, sizes up every role you're looking at, and keeps everything organized from the first application to the final interview.
No credit card required. 7-day free trial, then free forever.
Recreated from the real homepage, real copy. The headline is the whole positioning: this isn't about applying faster, it's about applying like you actually mean it.
Simple, credit-based pricing
Every account starts with a 7-day free trial. Every AI feature runs on credits from a monthly allowance, and topping up with a one-time pack never expires.
Free
$0forever
5 credits / mo
Starter
$9/ month
25 credits / mo
Pro
$22/ month
75 credits / mo
Recreated from the real pricing page. Credit costs are tuned per action (a full interview prep pack costs more than a thank-you email) instead of charging the same for everything.
Running it like a business, not a side project
A product with real subscribers needs real operating visibility, so there's a second application entirely: an admin dashboard behind its own separate login, with no shared session against the main app. It tracks revenue, subscriber tiers, AI usage, and the actual cost of every generation, not just what users see.
$75.00
Est. MRR
4
Paid subscribers
1
Starter subs
3
Pro subs
Tier distribution
Free 17% · Starter 17% · Pro 50%
Recreated from the real admin dashboard (generic demo data). Same panel also tracks total generations, tokens burned, and estimated AI cost, all pulled from production rather than estimated after the fact.
| Action | Credits |
|---|---|
| Resume tailoring | 2 |
| Cover letter | 2 |
| Interview prep pack | 2 |
| Interview session | 5 |
| Screening questions | 1 |
| Thank-you email | 1 |
Recreated from the real billing config. Every credit cost is editable from this screen, so pricing can move with actual AI spend instead of a hardcoded guess from launch day.
It doesn't remove the busywork of applying. It removes the excuse to only have one resume.