Why I Demoted Myself

Many adults would define a successful career as a series of steps up some sort of metaphorical ladder.  You start out in corporate life as an intern or perhaps as an entry-level employee.  In those jobs, you do whatever menial work your boss asks you to do, and it’s okay.  No, actually it’s great.  I still have fond memories of my internship.

I was fortunate to work for a small, science-and-engineering-based firm in the western suburbs of Chicago.  Moving from Upstate New York, getting established with an apartment and a credit card, being paid to work out geeky scientific bits of software routines, and going out to a different Chinese restaurant every Friday are just a few of the highlights of my experience.  Most importantly, I was accepted by a team of professionals who got along well together and worked hard to make a difference in the world.  That memory forms some of the basis for my beliefs about how a company should run and what my part in it should be.

That was back in the early 90s.  Jumping to today, I have spent the last nearly 11 years employed by Guidewire Software, a company dedicated to the property and casualty insurance industry (as opposed to medical or life insurance).  While insurance “paperwork” (virtual paper these days) is not as interesting as the science of my internship, the cause is important, and with Guidewire, I had once again found a small company of professionals who got along (i.e., without nasty politics) and worked hard to make a difference.

I joined Guidewire as a Senior Software Engineer.  At the time, no one cared too much about career paths or status at Guidewire, and that was a very good thing.  Titles were just a way to understand the loose boundaries of one’s work with a hint of the level of experience one had (e.g., “senior,” as in “not a beginner”).  After a couple of years, I was recognized to have leadership tendencies, and an out-going founder of the company tapped me to take his place as team lead.  That is when I stepped “laterally” to a management career path.

Over the years following, I moved from team to team, addressing the worst of each team’s dysfunctions, getting them unstuck, and in some cases seeing things through to successful delivery of working software.  Huzzah!  On teams full of software nerds, it takes one with slightly better social skills to push things along.  So that kept me busy for a number of years while Guidewire grew from a few hundred employees to a couple thousand.

Three years ago, I was interim Vice President of Product Development.  I had gone from team lead to Director of Engineering to VP of Engineering.  My former manager, someone I still respect highly, had a falling out with the CEO, and he left the company.  I was tapped by the CEO (also a founder) to “keep things going” while the search was on for a new department head, a product visionary for insurance technology.  Those five months were the most stressful of my life, although by the time we found someone, I was starting to get the hang of it.  Nevertheless, with the arrival of the new department head, I returned to my position as VP of Engineering.

One of the reasons for the falling out was a failure to produce new products or to make significant progress on moving our products to the cloud.  At this point, everyone knows the cloud is more than a fad.  At the time, there was a real “Innovators Dilemma” style conundrum about whether we would be cannibalizing our profits by offering new products that were competitive with our existing products.  I was decidedly on the side of outdoing ourselves, which is how companies stay youthful and competitive.  So I made a point of taking on product innovation and starting a team that would create new products in the cloud.

From around March of 2015 through the subsequent March, I led the effort to create “Digital” products, a funny marketing name (isn’t everything about computers digital?) that meant building software for consumers of insurance to access and update their  policies and claims.  Traditionally, Guidewire was focused on employees and sales agents of insurance companies.  Now, innovation tends to hold hands with failure, and sure enough, we experienced a number of failures on the way to eventually succeeding at creating a cloud-based product.  However, about a year into the project, we had an internal breakdown.

If success means being productive, being unproductive equates to failure, at least by my standards.  As the leader of an effort that melts down, I feel accountable for the utter lack of productivity.  As a manager, my job is to call out problems and get people to fix them.  The meltdown included my peers and managers being in denial that there was anything wrong, and nothing I said would change their minds.  So I resigned.

At least, that was my first attempt to resign.  California has “at will” employment, so an employee is free to leave a company anytime, just as the company is free to let an employee go at any time.  My letter of resignation was met with pleas for me to stay.  I could do anything I wanted, I was told.  I should just stay and find something I would enjoy.  So for the first time in my career, I exercised patience and waited.  While I waited, I worked on a couple of productive things, which was sufficient to ease my conscience.

Then the next opportunity to work on cloud products appeared during the summer of 2016, and once again I was tapped to lead the effort from the engineering perspective.  The situation was awkward.  We had no solid plans for what to do, but there was plenty of “vision” and “hope” that something good would come of the effort.

Did I say awkward?  Well, that situation was an even bigger mess than the previous attempt had been.  Apparently, the business side of the company had its own ideas, and before long, they announced an acquisition that was to become “the basis for our cloud-native solutions,” or some such marketing.  Again having led many people down a path that was ultimately unproductive, I offered my resignation.  This second attempt was also met with pleas to be patient and find something I would like to do.

So I decided to give up the glorious VP title and return to writing software.  Now I am a Staff Software Engineer (where “staff” means “even more experience than senior”), and relatively speaking, I am happy.  I am again part of a small team of professionals who work hard to make a difference, and I am able to make incremental improvements every single day.  There’s always room to apply my slightly better social skills for the good of my team, so that part works out too.

Outside recruiters tell me that I “should not be an individual contributor for too long,” as that would “jeopardize my status as VP.”  While that sounds ominous, when I think about it for more than a minute, I couldn’t care less about my title-based status.  I just want to be productive.

What’s your story?  Did you ever voluntarily “demote” yourself?  Leave a comment, and share your experience.


2 thoughts on “Why I Demoted Myself

  1. Dave, not recently, but when I first began managing, at Apple, I shifted back to programming – and managing – and programming – and managing… three times before I was clear that managing was where I wanted to go and supporting teams in that way was what I wanted to do.


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