Waypoint Career Design

Most career tools do the work for you. Waypoint coaches you to do it yourself — and that difference is everything.

Waypoint is a career development framework — four stages and a repeatable arc for developing a career deliberately. Miles, your coach, delivers that framework through conversation: recommending, challenging, and giving honest feedback based on your goals and history. The coaching adapts as you go: early sessions take a mentor's approach; as your sessions build, the questions get harder and the bar gets higher.

FOUR STAGES OF COACHING
Learn — Tell Miles what you want to understand or get better at. Get specific resource recommendations: books, courses, videos, and documentation — free where possible, always with a reason. Your learning becomes the foundation for everything that follows.
Build — Turn knowledge into real, verifiable work. Design and execute projects that cement skills and generate evidence you can point to. Get direct feedback on work in progress. Build a master resume grounded in genuine substance — Miles gives targeted feedback on every section; you do the rewriting.
Align — Shape your career trajectory based on what you have actually built. Discover role types matched to your real skills and experience. Evaluate opportunities clearly and position your story for the right ones.
Prepare — Practice interviews for specific roles and formats: screening, technical, behavioural, panel, case. Get direct feedback on every answer — what worked, what was weak, what to fix. Walk in confident because you did the work.
Running through all four stages is Waypoint's task system: commitments you make to Miles don't disappear when a session ends. They become tracked tasks you return to — turning a vague intention into a sequence of concrete, completable steps, with every session opening by asking how the last ones went.

BUILT FOR THE LONG TERM
Career development isn't a single job search — it's a years-long process. Waypoint is designed to stay useful across multiple roles and chapters of your career. Miles carries forward what you've learned, what you've built, your master resume, and your interview prep — so every new chapter starts from where you left off, not from scratch.

WHAT YOU LEAVE WITH
Most career tools are transactional — they produce an output, and the next search finds you back where you started. Waypoint is built to leave you with something that lasts: a direction grounded in real work, a repeatable method for managing your own growth, and a growing fluency in using AI as a thinking partner rather than an answer machine. Those capabilities compound. They serve you well past any single search.

YOUR DATA STAYS YOURS
Your conversations, context, and work are stored on your device and synced across iPhone, iPad, and Mac via iCloud. No account required, no data on our servers. Export your full history at any time.

Subscription Required
Waypoint requires a subscription to use. A 7-day free trial is available for new subscribers. After the trial, Waypoint is $49.99/year (billed annually) or $5.99/month. Payment is charged to your Apple ID account at confirmation of purchase. Subscriptions automatically renew unless cancelled at least 24 hours before the end of the current period. Manage or cancel your subscription in Settings → Apple ID → Subscriptions.

This app is subject to Apple's EULA: https://www.apple.com/legal/internet-services/itunes/dev/stdeula/