Will AI replace
your job?

Type your job title or paste a description. Toby gives you a free AI automation risk score and tells you what's protected and what's at risk.

42,006 job titles · proprietary automation scoring
Software Developer Registered Nurse Financial Analyst Graphic Designer Lawyer Accountant

115,000 tech jobs cut in 2026. Most announcements mentioned AI. Almost none of those companies tried retraining first. Not because retraining does not work. Because no one measured what was actually at risk versus what was worth keeping.

If companies will not measure before they cut, at least you can measure and act on it before they do.

—
How do you want your results?
Same score. Different delivery.
Honest
Clear breakdown of what may be at risk and what's protected.
Roast me
Toby tells you the truth -- with style. Powered by AI.
analyzing task structure...
Automation Risk Score
—
—
out of 100
—
6-factor breakdown
Repetitiveness
Input structure
Judgment threshold
Relationships
Regulatory sign-off
Data availability
At risk
Protected
Toby's read
—
What do you want to do about it?
Resume writer charges $250-$500  ·  Career coach charges $150-$300/session
vs. tobywins.ai $39/month
Most popular
Get interviews. We tailor your resume to every job posting.
Paste your resume and a job posting. We rewrite it specifically for that role -- the way hiring systems and hiring managers actually want to see it. Your first tailored resume is free.
1 Tell us about yourself -- 3 quick questions
2 Paste your resume and the job posting -- we handle the rewrite
3 Your tailored resume arrives by email -- plus your free AI risk report
First resume free  ·  Your AI risk report included
Get my free resume
After your first resume: $39/month for up to 200 tailored resumes per month.
Go independent
Turn your skills into your own business
Tap to explore →
If AI is putting pressure on your role, working for yourself is worth taking seriously. Toby walks you through four important steps -- from protecting yourself legally to finding your first clients -- and keeps you updated as things change.
You're in. Check your email for the four steps.
Build your skills
Upskill into safer ground
Tap to explore →
In regulated fields like healthcare, finance, and government, AI moves slower. The skills worth building are the ones that require judgment, relationships, and accountability. Tell us your industry and we will send you a monthly update on where your skills are most valuable and what is worth learning next.
Loading courses for your role...
We may earn a fee on paid courses. Free options always included.
Got it. Watch for your first update soon.
For Companies and Teams

Get the full AI workforce analysis for your team

Our sister company ActivateAI.nyc runs the full workforce analysis -- role by role, with a reskilling roadmap built in.

→Role-by-role breakdown across your whole team
→Automation timeline -- what's at risk now vs. in 3 years
→Reskilling roadmap focused on human productivity and creativity

No upfront placement fee for talent matches.