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If I was the CTO I would hire another vp with a different style and pit you against them and slowly move you out but he can't afford that so he is stuck with you for now.

Expecting the CTO to show up to standup meetings, expecting the CTO to help you do day to day tasks, and generally placing expectations on what your boss should be doing nevermind going to the CEO gently stab him in the back are things you shouldn't be doing. It is not your job to manage the CTO, why would the CEO give you that position knowing you will judge their performance at some point and go to the board the next time you feel overworked.

Tell the CEO there is too much work and you need more resources. Hire people to lighten your load. Take the new time/space to create a vision. Leverage your positive relationship with the CTO to get their support for new vision and use that to win the CEO over. Succeed with your vision and you will receive credit. When CTO moves on after you get purchased you move into that role.

Whatever you are doing now you better walk it back somehow and never share the nonsense you shared here with him/her. Think about it logically.. if the CEO fired the CTO and replaced them with you.. they lose historical knowledge plus a relationship that goes back to founding. You may or may not be able to replace them skillwise but it looks bad to investors. You would need to hire a replacement for yourself who will not be as good as you are. In the short term increased risk, less productivity and this is a startup so longterm doesn't matter because you hope to get bought out. Any CEO who would do this is foolish. Which is why you heard: "this is a concern you talk to him.." The CEO knows you are doing a great job and wants you to keep doing it but promoting you to CTO is a bad idea.. even if the CTO left chances are they go outside.

Your only strategy is to use the vacuum to do something impressive, then get people to replace your tasks and wait for an opening and you will be in a good position to land that role. Telling your boss he isn't working hard enough is not going to go well.




So executives can play politics but everyone else should just know their place? This is a bootlicker attitude.

More power to this guy if he thinks he can make a move and make it work out.


What I suggested is playing politics. Being so direct and about your ploy won't get you in the club. Create leverage before you try a power move.




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