The company I am applying for has 25 employees and is lead by the heads of marketing, personell, project management, and development.

I am offered the position of a CTO (head of development). My strengths and late experience has been in project and product management, group lead, CTO, and software architecture and less in the nitty gritty stuff of programming.

The company is well established (15 years plus).

What questions should I ask before accepting this position? I thought about questions regarding

  • Who is our true customer
  • Basic values towards share holders, employees, and customers
  • Which numbers will I be measured against, is the company measured against
  • What limitations are set on strategical decisions
  • How do we create an environment of creativity
  • How do we improve working as a team, company culture, and employee motivation
  • What kind of risks have you lay awake at night

Anything else?

  • When do I begin? EDIT - joke outside, the standard : what perimeter is the position, what income, what expectations, what objectives.
    – gazzz0x2z
    Dec 4, 2015 at 10:57
  • 4
    Is there really a board? Or are you just being given the CTO title? Actual board members have very different kind of contracts than executive management. So you may just be part of the executive management team; but the company has no official BoD. Dec 4, 2015 at 15:07
  • If really on the board, you may wznt to have a lawyer reviewthis to make sure you aten't accepting liabilities that wouldn't exist as a normal employee. On the other hand, you should be flattered to know that they trust you to help set the company's direction.
    – keshlam
    Dec 4, 2015 at 19:15
  • It will be the board, and it is no startup (15 years plus). Thank you for the tipp with the lawyer. Dec 5, 2015 at 8:46

2 Answers 2


So, from my experience of serving as a CTO for a company, these are some which I think you would want to ask:

  • What would be my roles and responsibilities?
  • What would be my equity and the norms for vesting?
  • What is the capital split? (while bootstrapping and if you are expected to contribute)
  • Am I responsible for the hiring and firing of the technical and R&D team? If not, why? If yes, then what are my limitations?
  • What would be my compensation like? Both in terms of perks, salary (if any) and stocks
  • This company has been around for more than 15 years, is well established in its market. No startup, sorry. Thanks for the questions, though. Dec 5, 2015 at 8:44
  • Ohh. Sorry for the edit, then :) But, the questions are still valid, except the capital split one!
    – Dawny33
    Dec 5, 2015 at 9:14

The usual ones before taking the position: What responsibilities would there be, what perks would come with the position, and anything else you'd need to know to decide whether or not you'd want that title. Some people may want details about what kind of power they could have, some may want to know about vacation time, and others may have other questions about that position that are worth discussing with others before saying, "Sure, sign me up for that role!"

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