Career Advice

Folks sometimes ask me for career advice, often including questions about titles and levels at each change. My advice is to worry more about the poeple and the assignment more than the title, and you'll see her that that is how I managed my career.

My final role at Interleaf was SVP Engineering and then SVP Marketing and Product Management.

At my next job (NetCentric), I was a VP of Engineering.

After I left that job, I wanted to brush up my development skills to more modern languages, so I took a job as a Consulting Engineer for six months for Jim Giza (someone who used to work for me).

After that, I started my career as an entrepreneur, starting my own companies for the next 20 years.

When my company Boston Light was sold to Intuit, I went from CEO to Director. (I was offered a VP position, but I preferred to come in as a Director so I could first prove myself to the engineers.) A year later, I was promoted to VP, when I was ready. A year after that was offered CTO but I turned it down, since I did not think I had the right skills at that time to be CTO for such a large company.

The lesson here is that career progression is not always about title. It is about putting yourself in the situation that would teach you the lessons you need to learn at that time. This means being careful about selecting which people you want to work with (people you can learn from) and working on things you want to learn.

Other Advice

  • Big company or small? There are important lessons with each, but vastly more important is simply to go to the place with the most stunning team you can find.

  • Don't worry about long term. Instead make sure you are signed up for a "stretch job" (going perhaps just a little bit beyond your current abilities) for the next year, and nail it. Once you have done an awesome job at that milestone, then think about what you want to do next. This approach will also make sure you "size" your career correctly-- not picking too big a goal that you won't achieve, nor too small a role that would bore you.

  • Try to be an optimist; trust people, move quickly, don't perfect things which don't need to be perfected. 30-Jul-2021