Career Days: From Developer to CEO Wrap-up

On Saturday, November 12th, we welcomed Canonical CEO Jane Silber to the Ubuntu Women Career Days to give us an overview of her career in tech from her beginnings as a Software Developer to her current role as CEO.

Laptop Keyboard

Career Path

Jane takes is through the path of her career so far

  • First became interested in computers in High School
  • Majored in Math/Comp Sci in college
  • Joined a software startup in a garage in Washington DC
    • Joined as a software developer, but also ended up doing a fair amount of research, statistical analysis, data modelling
    • Very classic startup: everyone working hard, doing all sorts of roles beyond your job description
  • Went to grad school for an MS degree in Management of Technology
  • Went to Japan for 2.5 yrs and worked as a software dev/researcher/manager
  • Returned to the Washington DC area and got a job with a small software company
    • Joined as a software engineer, moved in to team management roles and eventually became VP of the company
    • Spent 8 years at the company, and another 2 after the company was sold to another
  • Following that year she I moved to London, met Mark Shuttleworth through a mutual friend, and joined Canonical as COO in the summer of 2004 (Canonical started in April 2004), became CEO in March of last year

She also discusses some of the gender-based bias, both subtle and overt, she encountered and how she handled it.

Some advice she offers on the topic of the gender inequality in tech:

  • There is a lot written about girls/women in science and technology and she doesn’t subscribe to a single, simple theory about what is right or wrong or how to fix it, but there are a couple things that she has read over the years, that really fits with her experience. Studies show that
    • Men are more confident in the work place
    • Women express more self doubt about their abilities
    • Men are more likely to apply for jobs that they know they are not fully qualified for (in comparison to women applying for jobs they know they are not fully qualified for, not in comparison to jobs they are qualified for)
    • People doing hiring are more likely to judge men based on potential (e.g., “he’s got the core skills, he could do it”), and more likely to judge women based on experience (e.g., “she’s never done this before”)
    • In many/most people’s careers, there is a pivotal “stretch job” – the job that really pushes you beyond what you’ve done before
      • If she were to offer advice, it would be to be open minded, to look for the stretch roles if that’s what you want, to remember that you don’t have to have done everything before.


The session wrapped up with a Q&A session, with questions including:

  • What was the hardest part about transitioning from a s/w developer into a management role?
  • In your experience specifically and in your opinion about technical management in general, how important is it to have extensive programming experience when it comes to managing teams in a tech company?
  • Are you a part of any technical career organizations (think USENIX, ACM) or specifically women in tech organizations (WITI, Women in Tech), do you find value in them?

Full logs are available on our wiki:

If you’re interested in getting involved, please see the Ubuntu Women Career Days wiki page or email Cheri Francis or myself (

These sessions are open to the whole community, you don’t need to be a woman to attend or participate.

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