Why Winsly · Job search
Winsly and Simplify: autofill, and the case behind it
Use Simplify (simplify.jobs) to fill application forms fast, for free. Use Winsly to decide which roles are worth it and to write applications from your real wins, every line cited. Many people should use both: Winsly writes, Simplify types.
At a glance
| Simplify | Winsly | |
|---|---|---|
| Wins log, next-level bar and review case | No | Yes |
| Finding roles | Daily job matches from your profile; sources not stated | The job boards and career pages of companies you choose, scored daily |
| Fit scoring | Matches, with no must-haves described | Fit labels, with up to three must-haves |
| Tailored resume and cover letter | Yes (Simplify+) | Yes |
| Every claim cited and checked against your record | Not described | Yes |
| Autofill | Yes, free, on Workday, Greenhouse, Lever and more | No, by design |
| Auto-apply | Autopilot, included with Simplify+: up to 20 a week, submitted without a review step | No: you send each application yourself |
| Tracker | Yes, free | Yes |
| Phone app | iOS (Android planned) | Web, on any phone |
What Simplify does well
- A free, top-rated autofill extension: 4.9 from 3.8K ratings, 600,000 users (Chrome Web Store).
- A free tracker, and huge reach with students through its internship and new-grad lists on GitHub.
- Backed by Y Combinator, with an iOS app and introductions to hiring teams.
- Autopilot, now part of every Simplify+ plan, applies to up to 20 jobs a week for you, and fails an application rather than guess when it isn’t sure (Simplify).
Where Winsly is different
- Every line shows its source. Applications are built from a log of real, dated wins, not a rewrite of your profile, and every claim points to the win behind it.
- The bar in your manager’s words. A promotion track, with the bar, the wins that prove it and a review case. Simplify doesn’t attempt it.
- Fewer, better roles. Fit labels and must-haves you pin, so fewer forms are worth filling in.
- You always hit send. Winsly never applies for you.
Use Winsly with Simplify
Winsly doesn’t fill in application forms, and won’t. Simplify does that well, for free. Together, Winsly writes the application and Simplify types it in:
- In Winsly, prepare the application for the role, then Download all for the tailored resume and cover letter.
- In Simplify, upload the resume. On the free plan, Profile → Resume replaces your uploaded resume. On Simplify+, add it under Documents → Resumes and keep the others.
- Open the job’s application page and open Simplify’s Copilot panel. In its Resume section, choose the resume from Winsly.
- Click Autofill This Page. Add the cover letter if the form asks for one.
- Check every field and submit it yourself. Leave Autopilot off for these, since it submits without a review step.
Simplify’s own steps are in its help center: autofilling with Copilot and updating your uploaded resume.
Who should choose which
- Simplify if you’re a student or early in your career, applying widely, and want speed on forms for free.
- Winsly if you’re an experienced professional who wants each application to make a true case, and help growing where you are.
- Both is the strongest pairing: Winsly writes the application from your wins, Simplify fills the form, you click submit.
Prices, checked October 13, 2026
| Product | Price | Source |
|---|---|---|
| Simplify | Free autofill and tracker; Simplify+ $19.99 a week, $39.99 a month or $89.99 every 3 months, with 20 auto-applies a week. No refunds once active. | Simplify help center |
| Winsly | Free; Pro $20 a month or $200 a year; Advisor $50 a month or $500 a year | Pricing |
Prices and features change. See something out of date? Write to support@winsly.ai. Product names are trademarks of their owners.
Questions
Is Simplify free?
Its autofill extension and tracker are free. Simplify+ adds tailored resumes, cover letters and 20 auto-applies a week, for $19.99 a week, $39.99 a month or $89.99 every 3 months.
Does Simplify apply for you?
It can. Copilot fills in the form and you submit it. Autopilot, which every Simplify+ member has as of October 2026, fills and submits up to 20 applications a week without a review step.
Can I use Winsly with the Simplify extension?
Yes. Download the resume and cover letter Winsly wrote, upload the resume to Simplify, and let Copilot fill in the form. You check it and submit. The steps are above.
Which is better for experienced professionals?
For speed on forms, Simplify. For applications that make a true, specific case, and for the promotion where you are, Winsly.