Guide · Plans and privacy
Free, Pro and Advisor plans
What Free, Pro and Advisor each include, what Pro’s first 14 days add, and how win verifications and applications are counted.
Start free. Your wins, your Next Level bar and your review case are on every plan, and logging is never limited. Move up to Pro to make the case for your review and find your next role, or to Advisor for a CFO in your corner when it’s time to ask.
| Free | Pro | Advisor | |
|---|---|---|---|
| Price | $0 | $20 a month, or $200 a year | $50 a month, or $500 a year |
| For | Proving you’re on the way: your record, your bar and your progress | Making the case: everything you bring to your review, and job search | A CFO in your corner: when to ask, how to ask, practiced |
| Wins (from the box, a screenshot or an assistant) | Unlimited | Unlimited | Unlimited |
| Your Next Level bar and review case | Included | Included | Included |
| Manager updates | Included | Included | Included |
| Win verifications (a month) | 10 | 20 | 50 |
| Meetings read for your next level | — | Unlimited | Unlimited |
| Review case as a PDF | Not included | Included | Included |
| Self-review drafts and interview stories | Not included | Included | Included |
| Read your record from an assistant | Not included | Included | Included |
| Radar (roles found and scored a day) | Not included | 40 | 60 |
| Applications | Not included | 10 a month | 30 a month |
| Ask your advisor | Not included | Your first 14 days | Any time, plus it checks in on its own |
| The full playbook, with practice | Not included | Your first 14 days | Included |
| How your scope has grown | Not included | Your first 14 days | Included |
What’s on every plan
- Unlimited wins: type them, drop a screenshot, or log them from Claude or ChatGPT. Winsly tags each one.
- Next Level: your bar, the wins that prove it, and the review case on screen.
- Manager updates.
- Win verifications: ask someone who saw the work to verify a win (10 a month on Free).
Pro: make the case
Everything you bring to your review: your review case as a PDF with verified marks, self-review drafts and interview stories built from your wins, unlimited meetings read for your next level, 20 win verifications a month, and your record readable from Claude or ChatGPT. Pro adds job search too: Radar finds and scores roles against your search, and Winsly writes 10 applications a month where every claim is cited.
Your first 14 days on Pro include your advisor: ask it anything from Today, practice the ask, and get check-ins. After that, Pro carries on; keep your advisor with the Advisor plan.
Advisor: a CFO in your corner
A career coach costs about $180 an hour. Advisor is $50 a month and runs a CFO’s ten-year playbook on your own record: when to ask, what work to ask for, and practice for the conversations that matter, scored afterward. Ask your advisor any time. It checks in on its own, follows up on what you agreed in your meetings, and shows how your scope has grown.
When Winsly suggests a plan
Only when it helps, timed to your review: your review date if you’ve set one, your company’s review month, or the usual November–February season. About a month before, Winsly offers to turn your case into your self-review (Pro). About two weeks before, or once most of your bar is shown, it offers to practice the ask (Advisor). After the review, it helps you start the next cycle. Never more than one suggestion a week, never on the day of your review, and Not now quiets it until your next one. Winsly never emails you about plans unless you ask it to.
Why yearly
One review cycle to the next. A yearly plan keeps your record, your bar and your case working from this review to the next one, so the next cycle starts from everything you’ve already proven. It’s two months free on Pro and Advisor.
How applications count
Applications are on Pro and Advisor. One counts when it’s prepared, not when it’s sent, and your first one is on Winsly: Radar offers it once your search has found roles. You can add more applications when you need them.
Billing, plainly
- Monthly or yearly, never weekly.
- You see the price before you pay, and agree to it.
- Cancel any time in Settings → Plan. Your plan runs to the end of what you paid for, then doesn’t renew.
- A full refund if you ask within 14 days of any charge, monthly or yearly.
- An email 7 days before a yearly plan renews.
- When a plan ends you’re on Free, with everything you’ve logged kept.
See the full comparison on Pricing.