Guide · Updates
What’s new in Winsly
What Winsly can do for you, and when each part arrived. The newest is first.
October 2026
Winsly is open to everyone on Free
Anyone can now start on Free. Choosing Pro or Advisor asks if you’d like to be notified when it opens, and Winsly only emails you about plans if you say yes, from Settings → Plan or wherever a paid feature is locked.
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The Guide is one tap away, with What’s new
Guide in the sidebar and the account menu opens winsly.ai/guide, where What’s new now shows what Winsly can do for you and when each part arrived.
Winsly AI, at winsly.ai
The AI career coach for your next promotion now has its name and its home at winsly.ai, with everything you’ve logged carried over. See how Winsly compares with the tools you might already know.
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Suggestions timed to your review
Set your review date and Winsly paces itself to it: your self-review about a month before, practice for the ask about two weeks before, then a fresh cycle after. Never more than one suggestion a week.
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Sign in with Google or LinkedIn
Continue with Google or LinkedIn, or use a one-time link sent to your email: there are still no passwords. You can connect another way to sign in from Settings at any time.
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Add a meeting: a 1:1 with your manager, read for your next level
Paste the transcript or notes from a 1:1 or a review, and Winsly lays out what the next level takes, wins worth keeping and what you each agreed to, each with the line it came from. On Pro and Advisor.
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Get a win verified by someone who saw the work
On any win, Get this verified asks someone who saw the work to say it’s right, in an email you see before you press Send. They answer in seconds, and the win carries their name: “Verified by Priya N., peer”.
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One box on Today, and a win drafted from a screenshot
Today opens on one box: write what happened, or switch it to ask your advisor. Drop in a screenshot of praise in Slack or a number that moved, and Winsly drafts the win for you to check.
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A three-minute Winsly setup that ends with your resume aimed higher
Say what you want, add your resume, check the bar for the level above you and confirm a few wins. Then your resume rewrites itself for the level you’re going for, every line backed by your work.
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How to get promoted, step by step
A free guide to the four moves that get people promoted, with an answer for each question on the way: what it takes, whether you’re ready, how to ask, and what to do if you’re passed over.
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Practice how to ask for a promotion before you do it for real
Practice lets you rehearse a conversation that matters with a manager who pushes back, then shows how you did, with one of your lines rewritten the way it could sound. On the Advisor plan.
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Your advisor runs a CFO’s promotion playbook
On the Advisor plan, your advisor follows the method of a CFO who logged his wins and asked for the next level every cycle. About once a week it suggests one next move, timed to your bar and your review.
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Log work wins from ChatGPT or Claude
Connect Winsly to Claude or ChatGPT and say “log that launch as a win”: your assistant reads the ticket or thread and saves the win for you to check. Logging is on every plan, Free included.
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Interview stories from your strongest wins
Stories turns your best wins into what you’d tell an interviewer or a promotion panel, each opening with the lesson it proves, and shows which common questions none answers yet. On Pro and Advisor.
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Your growth: your scope, quarter by quarter
Your growth, under You, lays out the last two years by kind of work, from doing it to changing how the company works, and names the first time your work reached each. On the Advisor plan.
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Manager updates that get your work noticed
On every plan, Manager update drafts a short note about what moved lately, one line per win you choose, for your manager or your manager’s manager. You send it yourself.
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Self-review drafts from your wins, every line cited
When the review form arrives, pick the period and the questions, and Winsly drafts your answers from that period’s wins, around what your manager said the next level takes. On Pro and Advisor.
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Winsly plans: Free, Pro and Advisor
Start free with unlimited wins, your bar and your review case. Pro makes the case for your review and adds job search, and its first 14 days include your advisor; Advisor keeps a coach in your corner.
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A promotion case to take into your review
Review case picks up to three wins for each part of your bar, strongest first, every claim cited. It’s on screen on every plan, and downloads as a PDF on Pro and Advisor.
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Next Level: a promotion criteria tracker in your manager’s words
Paste what your manager said the next level takes, and Winsly turns it into a bar, links your wins to each part and shows what’s proven and what’s missing. On every plan, Free included.
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Your wins log, a work wins tracker at the heart of Winsly
Add a win in a line or two, and Winsly tags the kind of work and how much it matters: a brag document that keeps itself. A Friday check-in keeps the habit, and logging is unlimited on every plan.
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September 2026
An AI career advisor that has already read your record
On the Advisor plan, ask about your review, a role or your next move, and your advisor answers with your wins and your bar in view. It drafts changes for you to approve and never sends anything.
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A tailored resume and cover letter from your work, every claim cited
On Pro and Advisor, Prepare application writes a resume and cover letter for any role from your own record, every line showing the win it came from. You check it and send it yourself.
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Radar: job alerts from company career pages
Winsly watches the companies you care about, reads their own job boards and career pages, and scores new roles against what you want, with up to three must-haves. On Pro and Advisor.
More in Radar