1. Get into bigco for three years and work hard to learn tech skills while being at bigco.
2. Join tinyco1 as CTO and apply your skills to build something real. If tinyco1 becomes mediumco1 within 1/1.5 years stop - you have arrived.
3. If tinyco1 feels shaky as a business after a year / year and half move to tinyco2 as CTO. If tinyco2 becomes mediumco2 within 1/1.5 years stop - you have arrived.
4. Join mediumco3 as cto citing your rich and varied experience.
A startup CTO is most likely to be the first developer in the company. He should be able to make the first MVP.
This implies backend, front development and Ops skills.
After 2-3 years of experience, join a tiny company as co-founder/CTO.
If it works, you have arrived.
If it doesn't, your experience will allow you to aim for a bigger one.
Don't apply, let people know you, grow your network and make people want you to build their product.
2. Join tinyco1 as CTO and apply your skills to build something real. If tinyco1 becomes mediumco1 within 1/1.5 years stop - you have arrived.
3. If tinyco1 feels shaky as a business after a year / year and half move to tinyco2 as CTO. If tinyco2 becomes mediumco2 within 1/1.5 years stop - you have arrived.
4. Join mediumco3 as cto citing your rich and varied experience.