I was the second hire at a company on Y Combinator's Top 200 list
Tags: convictional, yc, webdev, resume
Published: 2023-08-05 06:16:04

## TLDR;

I spent the past four years as a Senior Software Engineer at [Convictional](https://www.ycombinator.com/companies/convictional), a venture-funded B2B ecommerce software startup. I was the second hire at the company and am credited as the #1 contributor to the codebase on GitHub (written in Go). During my time, Convictional grew to over 50 employees and reached spot #199 in YC's [Top Companies by Valuation](https://www.ycombinator.com/topcompanies/valuation). 

For this next chapter, I'm looking for a new values-centered company that I can support with my learnings and enthusiasm! 

## Skip ahead...

- [**A humble admission**](#a-humble-admission)
- [**Convictional in a nutshell**](#convictional-in-a-nutshell)
- [**My contributions**](#my-contributions)
- [**My learnings**](#my-learnings)
- [**Where do I go from here?**](#where-do-i-go-from-here)

---

## A humble admission

I'm extremely fortunate to be able to say this.

With about [4 million software engineers](https://en.wikipedia.org/wiki/Software_engineering_demographics) across North America, it comes with a sense of pride to belong to the 0.01% that can claim the niche statistic in the headline. But if I'm being candid—as I hope to be for the rest of this post—every senior software engineer that I've met has had plenty to teach me. It doesn't so much matter where you work, I think.

In fact, in those early days at Convictional, Chris and Roger emphasized that our goal in growing the team was "to hire people who were smarter than us" and I believe we held true to that. So by exposing my earliness I'm also admitting to a certain level of underqualification.

I embrace this wholeheartedly. Running interviews is _so_ much less stressful since accepting that it's okay—preferred, actually—for the interviewee to know more than me. To this day I still get that initial spike of nerves when a conversation moves towards some common technologies I haven't explored like Docker, Kafka, or Oauth.

The bottom line is, I guess, that my journey is just beginning. I had an exceptional first chapter though, so don't stop reading 😁.

## Convictional in a nutshell

Chris and Roger were working at Shopify when they came up with the idea for [Convictional](https://www.convictional.com/).

An early version of the product was made—a platform that connects the ecommerce systems of retailers and suppliers to enable dropshipping—and they were accepted into Y Combinator's accelerator as part of the Winter 2019 batch. At YC, [Convictional raised $2.2M](https://www.convictional.com/blog/convictional-raises-2-2-million-usd) and TechCrunch placed them in the [top 10 of the 200 startups](https://www.convictional.com/blog/techcrunch-selects-convictional-as-a-top-10-y-combinator-company) in the batch.

While this was going on, I was wrapping up my fourth-year engineering design project at the University of Waterloo. Roger and I had worked together in the past and he was keeping me updated on Convictional's successes in California. I had always been intrigued about working at a startup, and by April 2019 I had joined the team, just a few weeks after our first hire, Matt.

The next four years are best described as a punctuated equilibrium, rather than the roller coaster often associated with Silicon Valley startups. Most days were productive yet uneventful in the grand scheme, a good thing for the human psyche I think. 

Roger and Chris poured meaningful hours into developing a humane work culture that is uniquely their own. No weekends, no Slack channels, and no engineer-on-call are all examples of ways—still in effect today—that they balanced _focus_ with _rest_ from day one.

Convictional's secret weapon here was Jess, our third hire, who brought with her a Masters in Adult Education and Workplace Learning. We read books, adopted mindfulness, and leaned in heavily to async practices. The people we hired often told me in our one-on-one syncs that Convictional had a healthier culture than their previous workplaces.

By the time I'm writing this, Convictional has grown to a 50 person company. We've attracted some [recognizable logos](https://convictional.com), closed subsequent [Series A](https://www.convictional.com/blog/convictional-announces-series-a-funding) and [Series B](https://www.convictional.com/blog/announcing-our-40-million-series-b-round-to-help-retailers-launch-new-brands-on-their-dropship-marketplace-and-wholesale-programs-in-days) rounds of funding—landing us at spot #199 in YC's [Top Companies by Valuation](https://www.ycombinator.com/topcompanies/valuation)—and continued to put our values ahead of profits.

## My contributions

As much as I laud Convictional's culture and team-building, I should be clear that my own contributions in that arena were the quiet and indirect sort. I joined the team as a software engineer and stuck to the individual contributor track throughout my four years there.

Here are the highlights of my proudest work:

1. As of May 2023, I'm credited on GitHub as the #1 lifetime contributor to Convictional's main backend codebase, with 520 commits. This is a server application written using Go and MongoDB and tightly integrated with some major ecommerce APIs such as Shopify, WooCommerce, and Stripe.

2. As our team grew I took on ownership of our API architecture and design. I wrote our API style guide, maintained our [public API documentation](https://developers.convictional.com/reference/introduction), and worked with the team on all aspects of API enablement. This included some things like designing new APIs or consulting with those who did, improving our monitoring for API-related metrics, introducing auto-generated API docs using in-code annotations, and defining our API versioning procedures.

3. From 2020 to 2021, I worked on a special project with a well-known Canadian retailer's engineering team to build them a standalone integration bridging our two systems (using Go, MongoDB, and GCE). As my first collaboration, I quickly learned about the challenges of navigating organizational complexity. The project was late but successful, and ended up converting them into our largest customer. A few months later, [we secured $6.7M in Series A funding](https://www.convictional.com/blog/convictional-announces-series-a-funding).

4. By 2022, we started to have new engineers joining the team each month. This gave me a treasured opportunity to practice more peer leadership as an individual contributor. I doubled down on making PR reviews my top priority and was delighted whenever I could approve within minutes of the request. I made daily efforts to respond to questions from team members by writing improved documentation. I shared learnings more intentionally across the team and hosted "lunch & learns". This sort of team contribution is now my favorite part of the job.
 
## My learnings

Here are some takeaways I have from my time at Convictional. I don't think any of this is earth shattering, but hopefully I've chosen well enough to provide something of interest.

**1. Work at a company where you feel honored.**

_I got my first 12% raise within a couple months of being hired. Roger told me, "we started you out on the low end, but it's obvious you're worth more than that". This sort of proactive wage increase became a pattern that continued all four years._

Convictional applies what might be deemed "radical trust". All employees have access to the company metrics and investor updates, including our burn and runway. We worked remotely before it was cool while being adamantly against surveillance tools. 

Chris and Roger assured us that if they couldn't trust us they would rather just let us go. And they lived up to that too. We were able to enjoy a high-performing team because toxic individuals that slipped through the cracks were quickly removed.

There's a lot more I could mention here and I think this must be what happens when values flow top-down through an organization—they show up everywhere. You can pick up on it during the hiring process too. Look for companies that post salary ranges upfront, share employee handbooks, and go to greater lengths for a humane hiring process. For example, [Mindera is looking pretty smug right now](https://mindera.com/careers) 😉.

**2. Our biggest engineering bottleneck was support.**

This was true on day one when I was hired, and I think it's still true at Convictional today, though it did get markedly better once we hired our all-star support team (thank you Dan, Danielle, Jared, and Ty 😭).

I think this is an example of where learnings were left on the table at Convictional. I don't think we quite figured this one out. Because, in theory, this is a great thing—people care enough about the product to complain about it! I suspect that this is exactly where you _want_ your bottleneck to be.

Our shortcoming was that we didn't land on a way to leverage this rich support data arriving hourly _back_ into the product roadmap in an elegant way. There were support tickets we first saw in 2020 that were still plaguing engineers in 2023. There were complaints coming in repeatedly that engineers were diagnosing from scratch each time rather than building up in a knowledge base. As our issue tracker filled to the brim, we would just archive the oldest tickets to clean it up.

As one of our earliest engineers, looking back I consider this a personal failure. I can't wait to try again.

**3. Eliminate toil enthusiastically.**

First, a quick clarification. "Toil" isn't just any tedious task, in my opinion. It's a tedious task that _also_ feels ineffective or wasteful. That nagging "there _must_ be a better way" is a sign of toil. It's the pain of feeling like your pain is for nothing.

Eliminating toil for the other engineers at Convictional was one of my highlights. I've already written [an article](https://dev.to/jakestrang/moving-standup-meetings-to-google-docs-30j7) about how early on we eliminated the toil common in typical daily standup meetings (that "can we be done yet?" feeling). The "oh thank GOD" moment that comes from making broken things better is something the team should experience regularly.

There's a lot more that I'd like to experiment with in this area. Like, can all the toils of a team be enumerated and tracked in a spreadsheet? How much of the psychological weight of toil is lifted if we communicate about it better? 

## Where do I go from here?

Chapter one is over. It's time for chapter two to begin.

One thing I've tuned into this year is that I care a lot more about people than I do about software. I see code as a means to delighting someone and I'm not as interested in deepening my backend knowledge for it's own sake. I'm also a feeling and intuition-driven person rather than thinking/sensing. All of this has me considering whether software engineering is where I'll find my tribe in the long run, or somewhere else entirely!

For me, I get excited about making things that other people will get excited about using. I like the puzzle of the design, how to make the pieces fit together elegantly? I like the challenge of the execution, how to sequence the project to bring it to success? I like the feeling of leadership, how do we come together as humans with a common goal while embracing our best selves?

So perhaps another startup could be a good fit, ideally one with a product that's more tangible and closer to consumers, away from the ecommerce space. A values-centered company looking for senior/staff engineers that will add to the culture. Maybe even something that's addressing humanity's biggest concerns head on?

Or, maybe 6 years in tech is enough and it's time to try my hand at toy making 😄.

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### Got an opportunity you think I'll like?
[Find my contact info on my resume here](https://drive.google.com/file/d/11eRTiqswz8FeFfWY8o-_jSCqH6QndwKV/view?usp=sharing).