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Connected (now Thoughtworks)

Toronto, Canada · May 2016 – Mar 2017

I interviewed with what was known as Connected Labs while I was still at OANDA. It was a one-stop shop software consultancy that combined design, product management, and software engineering expertise.

I always felt a bit strange about building software that I don’t maintain long term, but Connected offered modern software stack & practices, a secret internal project that would be its own product, and compensation that felt reasonable for my experience.

Given my rapid exit from PaymentUs, I was happy to be back working in a modern software business in the heart of downtown Toronto. Funny enough, Connected was in the same building as OANDA, just one floor up.

The Work

Software Engineer - Internal Project (May 2016 – Jan 2017)

JavaScript Node.js Redis Socket.IO MongoDB

I was immediately put on the internal project, Olympus, building an ambitious Internet of Things (IoT) platform.

It was mostly still greenfield, with the architecture set up by Daniel, a senior engineer, and lots of feature work to do. A few of us early career engineers & interns put in good effort trying to reach some imaginary feature parity before we’d start demo’ing it to potential clients & investors.

As Daniel transitioned to revenue-generating client work, I assumed some leadership responsibilities: managing the roadmap, making key technical decisions, and reporting directly to Damian, Connected’s VP Engineering. Robert, an experienced business person, was brought onboard to prepare for spinning off the project into its own entity, contingent on product traction and investor interest. I even attended a pitch presentation with a very well-known consumer electronics brand in Boston.

As we got to the end of 2016, I was informed that we had reached the allotted time of incubation, and the spin-off was not to be. Robert left to do his own business, and the engineers (including myself) were repurposed to work on client projects.

Software Engineer - Client Projects (Jan 2017 – Mar 2017)

Java Spring Boot

I joined a few fellow engineers to work on Loblaw Digital’s Click-and-Collect order picking app backend.

It was clear that it wasn’t a good fit for me, as I didn’t have the finesse to work onsite, directly with the clients. So this stint didn’t last long.

Exit

Having had a little taste of being a “product manager” on the Olympus project, I got the idea that PMs were more influential than engineers, as they seemed to be the ones deciding what to do. I knew I didn’t want to work on client projects to start with, so as soon as I was back on the bench, I started looking for PM roles externally.

Takeaways

Connected is where I had my first exposure to the modern web stack.

I also got my first taste of being a PM and a Tech Lead here. Trying to guide a young, small team towards a place I’d never been taught me a lot about leadership, people management, and humility.

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