The course guide

Meet your caddie.
Fun sprite, serious game.

Every evening: trawl the boards, decode the JD, re-tweak the CV, fight the ATS form, draft answers to screening questions, hunt for the hiring manager. Those are the eight holes. Caddie plays them ahead of you, properly. You take every swing.

learn ↻ re-ranks the round & teaches the drafts 1 2 3 4 5 6 7 8
Hole 1
Scout the course
~50 boards and the career pages you watch, swept daily. ~10k live roles.
daily sweep 06:00 ▮
We Work Remotely3 found · 2h ago
Landing.jobs5 found
GermanTechJobs2 found
Mind the Product1 found
…46 more boards + your watched career pages · ~10k roles checked
Hole 2
The score cascade
Not one score. A cascade built from your profile at onboarding: a hard location gate, then the machine read, then a recruiter read against your rubric, your weights, your priorities.
The two reads disagree? That is signal. Wrong in substance gets skipped; wrong on paper gets a pack that closes the vocabulary gap.
scored against your profile
Senior PM, Payments · Acme (fintech)84
your rubric · set at onboarding: skills 30 · domain 30 · remote 30 · stage 10
0→1 remitb2b saasfounder-friendly
1location gate · full-remote EUpass
2machine read · the filters’ viewkw 9/12
3recruiter read · against your rubric84 · “your lane”
Hole 3
Pull the real brief
The full JD, fetched live from the source at draft time. ATS named, the employer’s real screening questions pulled.
Ashby · detected JD · live from source

“…you’ll own our wallet roadmap as we rebuild payments under PSD2, working directly with the founders…”

screening questions, pulled
  1. Why Acme?
  2. Do you have the right to work in the UK?
  3. Describe a payments product you shipped.
Hole 4
Find the angle
Company research, distilled to the one angle that leads your whole pack.
company research
  • rebuilding wallets under PSD2 · careers page
  • Series B · 60 people · London · press
  • expanding UK to EU next year · founder blog
▼ distils to
angle: took a payments product 0→1 in a regulated market
Hole 5
Beat the parser
Drafting starts with the machine. The exact ATS this application enters sets the format rules before a word is written, because every system parses differently.
ats rules, loaded first Ashby · this role
parse check88
  • ✓ single-column layout: tables Ashby can’t parse, dropped
  • ✓ dates normalised to MM/YYYY, the format its parser expects
  • ✓ JD’s exact phrasing kept: “payments product”, not a synonym
  • ✓ variants covered: “re-platforming” and “replatforming”
every system parses differently. Workday would get a different tune.
Hole 6
Build the pack
Inside those rules, the pack is written for the human: CV, cover letter and screening answers, all led by the angle. Every change shows its original and its reason.
CV · Cover letter · Answers (3)
summary line
Led payment initiatives across several products.
Took a regulated-market payments product 0→1, launch to first 10k users.
why: the JD asks for “experience launching payment products under regulation”. Quoted at hole 3.
cover letter opens
“You’re rebuilding wallets under PSD2. I’ve taken a payments product 0→1 in a regulated market, and…”
Hole 7 · yours
You take the swing
Review it line by line. Change anything. Send it yourself. No auto-submit, ever.
Take your first swing — free
your review
Led payment initiatives across several products.
Took a regulated-market payments product 0→1…
✓ keep✎ edit↩ original
change 3 of 7 · nothing sends until you do
you hit send, from your own account, on the employer’s own form
Hole 8
Warm the follow-up
The right people at the company, found. A short, grounded intro, drafted.
the follow-up
Maya K.Head of Product · Acmewarm intro
Jonas R.Talent Partner · Acme
“Hi Maya, saw you’re rebuilding wallets under PSD2. I took a payments product 0→1 in a regulated market; happy to share what worked…”
58 words · drafted for you · yours to edit and send
↻ between rounds
Caddie learns
Every skip, save and edit re-ranks tomorrow’s round, and teaches the drafts your voice: what you keep, what you strike, how you phrase it.
tomorrow’s round re-ranks
▲ 88Payments Lead · fintech scale-up
▼ 41Growth PM · web3 exchange
…and the drafts learn your voice
✎ you rewrote the summary line → future CVs start from your wording
✗ “synergy”, struck twice → never drafted again
because yesterday you skipped 3 web3 roles, saved 2 payments roles, and edited 1 pack
🎒 in the bag · what each hole leaves you with, and the time it saves
found on We Work Remotely → the evening trawl, donesaves ~15–30 min
gate → kw 9/12 → AI 84 → no maybe-fit guessworksaves ~10–15 min
Ashby · 3 Qs pulled → no surprise questionssaves ~5–10 min
angle locked → opens with why yousaves ~15–30 min
tuned for Ashby · parse 88 → survives the filterssaves ~10–15 min
pack built · CV+CL+answers → evening savedsaves ~30–60 min
sent, by you → you stay in controlyour ~5 min
2 people · intro drafted → warm intro, not cold applysaves ~10–20 min
re-ranked + your voice learned → sharper every roundcompounds
the slow way, per role: ~1.5–3 h. with Caddie: your ~5 min review.~1.5–3 h saved
House rules

No auto-submit

Caddie drafts and fills; you review and send every application yourself.

Never invents a fact

Where something's missing it leaves a visible placeholder, not a fabrication.

Auditable by design

Every tailored change shows its original text and the reason; the job ad is quoted verbatim.

You take every swing

Caddie reads the course and hands you the club. The shot is always yours.

See it score your career.

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