I moved to New York for a startup job that lasted seven months.
Peek made a small, dedicated mobile device for email and messaging. The idea was simple enough to explain, but the service behind the device depended on reliable managed connectivity and infrastructure. I joined in August 2009 as Director of Technology Operations, after three years at Beatport, because I wanted the New York startup experience and a new kind of systems problem.
I introduced agile methods and helped build Peek's first physical data centers to augment its cloud infrastructure. Then the funding ran short. By March 2010, the organization was forced to move on.
That was the version I wrote later that year in a cover letter. We did real work, and the company still ran out of money. The role lasted seven months.
I moved quickly because I had to. In March I became CTO of Reality Check Network, working in the ServerStack orbit. The business made infrastructure the product. I was responsible for roughly 1,400 servers, a team of twelve, and seven data centers across New Jersey, Amsterdam, and San Jose. The geography alone changed the job. A customer problem, a vendor problem, a staffing problem, and a physical data-center problem could all be the same problem, only several time zones apart.
We worked on scalability in the hosting systems and in the way the engineers and administrators operated. The company was growing fast. I was proud of the progress, and I was still looking.
When I first came to New York, I had applied to Shutterstock for a technical project-management position and received an offer. I turned it down because the role did not fit what I wanted. I was looking for a position with more responsibility and direct ownership of technology operations.
After Peek ran short of funding, turning down the earlier offer was harder to look back on.
I kept in touch with somebody I knew inside Shutterstock and kept hearing good things about the company. By September, there was a director role in systems operations that lined up with the work I had been doing and the responsibility I wanted. I wrote that I could bridge the gaps between technology and business, build teams, and solve the infrastructure problems created by growth. The language was confident. It needed to be. I was asking them to look past two short startup chapters and see a pattern of taking on larger systems.
Shutterstock hired me in October 2010.
Two months later, I described the year to an old connection as "startup hopping" around New York, building relationships and rebuilding technology teams. I called Shutterstock a kick-ass growing organization. There were about 160 people at the company by my count then, with plans to grow substantially the next year. The company had momentum and plenty of infrastructure work.
I was also building another thing on the side.
I had pulled together a small group of programmers around an idea called OpsDojo. We wanted one interface for managing data-center and cloud infrastructure, a common tool set for automating physical resources and virtual instances. The plan was to launch a beta into the open-source community. I was excited enough to tell people that we were getting ready to make some waves.
At the end of 2010, I had a new director job, two short startup roles behind me, and an infrastructure-management side project. OpsDojo still needed substantial work before an open-source beta would be useful. Shutterstock was growing and required my full attention during the day.
I arrived at Shutterstock with experience from a mobile startup that lost funding, a hosting business spread across seven data centers, and an earlier decision to turn down a role at the same company. The short jobs still gave me relevant experience with teams, infrastructure, cloud services, physical data centers, and rapid growth.
By the end of 2010, my position is clear for now. I am at Shutterstock, the team is growing, and there is a lot to do. OpsDojo remains a side project while I learn the systems and take on the rebuilding work in the new job.
-Chris