My Career Story

Reflecting upon the past sets the context for the present. It also reveals a system of behaviors which can we improve upon once we understand them. In my mind this story is the foundation of that system.

My Career Story
Photo by Etienne Girardet / Unsplash
Now this is the story all about how,
My life got flipped-turned upside down,
And I'd like to take a minute,
just sit right there,
I'll tell you….

My career story.

Reflecting upon the past sets the context for the present. It also reveals a system of behaviors which can we improve upon once we understand them. In my mind this story is the foundation of that system.

This article and it’s financial disclosures take inspiration from Will Larsen’s post of the same name. Inspiration also comes from my early years sharing salaries with friends. I wish we still did it. As with Will’s article this is a different framing than I use when I’m trying to impress folks.

The Delta

I was born and raised in Stockton, California a city known for it’s hub on the River Delta. I grew up in a middle class family where my Dad worked and my Mom took care of the family.

I have fond memories of searching AltaVista for pictures of my favorite Star Wars characters on my uncle’s Mac when I was 12. When we got our first Windows computer I spent all my free time on it. From then on, I knew my future was in technology.

I lived in Stockton until I transferred to San Francisco State in 2003. With no particular goal in mind, other than to avoid math classes and be in tech, I chose to major in Computer Information Systems.

During my final year in San Francisco I started a company, Bay InfoSystems. It seemed like a good way to make some money and springboard my entrepreneurial side. I managed to get a few big clients and made enough money to get a payroll service to pay myself as an employee. Unfortunately it wasn’t enough and I didn’t have the desire to hustle more.

Silicon Beach

After graduating I moved to Los Angeles and got my first job at AIG Sun America as a QA Analyst. My offer letter was for $45,000. I remember trying to negotiate and the recruiter told me I had best take the offer.

I often describe myself as falling into the job of software testing. It was pure luck. My girlfriend at the time started working at AIG few months prior. She gave my resume to an internal recruiter who hustled me around for several job openings. I don't remember much about my interview with the Test Manager other than I focused my answers on writing documentation.

Years later a friend who had been an executive at AIG when I got hired told me how lucky I was. His impression of candidate Chris interviewing for several open engineering positions was I didn’t know what I wanted. He told my boss not to hire me. She hired me anyways. He was right, I got lucky.

I had no idea what I was doing. Luckily I was working with people who knew more. I learned a bit and more importantly made many friends. As those friends started to find other companies to work for and got paid more, I followed.

A year and a half after joining AIG I found a job at Countrywide Mortgage working on their loan origination application. The job was 3 months contract-to-hire, the first and only time I’ve ever done such an arrangement. I remember my contract rate being a lot more money than I was making prior. When they converted me to full time, I got paid less than the contract rate. I want to say my pay was around $68-70,000. The job and company ended up being a bit of a disappointment. I wasn’t challenged, nor did I particularly enjoy working for a bank.

A year later, a friend was leaving his job at a nearby startup and wanted to refer me as his replacement. Conversive, Inc. was selling an enterprise conversational automated chat application. They were rebuilding the whole thing, migrating it from desktop to web. The challenge of helping build a new web application enticed me. With my friend’s recommendation I joined at $80,000.

Conversive was my first experience as a sole tester and my first time working in a startup. Given the challenges we faced and my new autonomy, lots of things changed for the better. Rather than take a slow scripted approach to testing, I took a rapid exploratory approach. I bought testing books, started going to conferences and dove into my craft. Anything I could learn and experiment with, I did. I got my first promotion as a result and thrived in our supportive work environment. Over a decade later and I still talk to many former teammates.

After nearly five years there at Conversive we hit a wall. No one but the CEO knew the company was in financial trouble. One day the telecom company Avaya came in and bought us in a fire sale. Rather than stay on at the new company, one engineer left. Everyone else including myself declined our offers to join. It was our way to show how dissatisfied we were with the transition.

Avaya raised all the offers and we accepted. I joined Avaya for $105,000 in late 2012. Less than a week after the acquisition closed I got a VISA for India. Two weeks later I was on a three week trip to Pune in Maharashtra, India to train my testing counterparts.

Avaya's management was in the United States, developers were in Ireland and testers in India. My new boss made sure I understood how this structure affected decisions. As my workload declined it was clear the company would view me as an expensive team lead. I began looking for my next startup.

Impressed by my StackOverflow contributions, the CTO of a local startup recruited me. I joined Doctor Evidence at $110,000 as a Software Test Engineer in mid-2014. The promise and appeal of joining was as the company grew, I'd be able to grow into a management position.

Over the next three years our engineering team doubled. To keep up with increasing developer productivity, I spent more time automating tests. It was challenging and fun, but something was missing. Avaya was my first remote position but I already knew everyone on the team. Doctor Evidence was my second but I knew almost no one. Outside of not feeling like a part of the team, my boss rarely spoke to me. No 1:1s, no feedback on job performance, no raises, nothing. Time to move on.

In the beginning of 2017 I joined Laurel & Wolf as a QA Engineer at $110,000. I’d be going back to work in an office with a growing startup that had raised lots of money. It was a lateral move but I took a chance on a company I thought was set to grow. They had a defined engineering culture and leadership team in place. Finally!

From the moment I joined, it only shrank. Yet the core engineering and product teams were close knit and worked well together. We were a thinning band of engineerings helping each in any way we could. I was ready to go down with the ship. In the end it was a worthy journey with a great team.


After a three week job search I joined BloomNation, a startup helping to empower small businesses. In the four plus years I've been here we've gone from one business to four and rebranded to Promenade Group.

A few months after I started with BloomNation, I joined the Board of Directors for the non-profit Association for Software Testing.

As happens, when you open yourself up for new challenges you often get them all at once.