Transitioning from a large company to a 25 person startup

November 14, 2019

  • career
  • reflection

An engineer’s observations on people, process, and purpose

Originally posted on Medium


Between any two companies, there are always going to be differences. However, those who move from a big corporation to a startup (or vice versa) may be especially prone to experiencing “culture shock” moments. It’s been nearly four months since I made the transition from engineering at a very large company (think hundreds of thousands of employees) — to engineering at Informed K12 — a twenty-five person startup focused on solving operational challenges at school districts. A handful of my coworkers at Informed K12 have asked me, “What’s different about working here?” My response has been, “Everything.

Noting that my experiences and insights are unique to myself and Informed K12, here’s what popped out to me as feeling different.

I have the opportunity to engage with non-engineers.

Now when I say this, I don’t mean to imply that I have something against engineers. Interacting with anyone outside of engineering, and having visibility and context as to what was happening outside of my immediate engineering team was just totally new to me. At my previous worksite of thousands of people, at least 80% were engineers. This meant that my day-to-day interactions were limited to engineers, and my scope of vision was entirely around engineering-focused topics. At a large company where there are hundreds of moving pieces and layers, it makes the most sense for engineers to tune out everything that is not relevant to their immediate work. However, being siloed in this way with little understanding of what was outside my codebase, there were times when I felt like a “cog in a wheel.”

Thus, it was a culture shock for me to come to Informed K12 where the entire company — customer success, operations, customer support, sales, engineering — works in close proximity in the same room. I was astonished that by simply keeping my ears open, I could have a general sense of things happening within the company. Coming to Informed K12, my scope of vision is greater than ever before.

Even beyond casual interactions which can follow naturally in any closer-knit working space, at Informed K12, there is a need to keep communication going between different teams due to the extremely interconnected nature of our work. As engineers, we can’t silo ourselves from other members because the work we do directly impacts other members in the company. if the customer success managers are bombarded with phone calls, or customer support swamped with support tickets, it signals that there’s an engineering issue that needs to be addressed. If engineers have made an error or oversight, the ones who must follow up are our other team members. It’s absolutely vital that we communicate and work together with others to ensure the problem reaches a resolution. There are ongoing conversations between customer success managers, support, and engineers on slack channels like, `ask_an_engineer`. By having an awareness of the pain points that our co-workers face in their day-to-day, we are able to build internal tools that would alleviate their workload — without any empathy, awareness, or cross-team communications, it would never cross our minds to build these tools.

At Informed K12, it’s very clear to me where my engineering work fits in, where other people’s work fits in, and how these different pieces come together in the greater scheme of what our company is aiming to accomplish. While my day-to-day work revolves around engineering, it is also my responsibility to have a sense of awareness of what’s happening outside. When I take one look up from my computer screen, I can see the bigger picture, which leads me to my next point.

I understand what I’m working for.

This is something that should be a given, but often is not. A large company may have their fingers in multiple arenas of the market, making the overarching mission broad and ambiguous. By contrast, startups will tend to have a single focus, and attract people who are committed to a shared goal. It’s likely that each person at a startup views their work not simply as work, but as a means to evoke change.

At Informed K12, whether one is an engineer or a customer success manager, each person is ultimately working towards the same mission of alleviating challenges at the school district level. In fact, several of my coworkers are former educators who joined to make a system-level impact on the education system. Even from how onboarding process is setup, it’s clear that at Informed K12, engineers are expected to have a comprehensive understanding, and care about more than coding.

In my first few weeks, aside from traditional engineering onboarding related to environment setup and team coding practices, I went through a company-level onboarding which sought to give every new Informed K12 employee a base foundational understanding. In one session called School District 101, I had the chance to learn about how school districts are organized, what the day-to-day of a school district administrator might look like, and the various challenges they face. In History of Informed K12,I had the chance to sit down with the two co-founders, Sarah and Qian, and hear directly from them their motivations behind starting the company, and the challenges they had faced along the way. These various onboarding sessions I experienced were personal and comprehensive — no matter one’s role at Informed K12, it establishes shared understanding of our work.

In my second month at Informed K12, my manager encouraged me to attend a school district onsite — an opportunity that I would have never imagined at my previous company. During this onsite, I had the chance to hear directly from various school district administrators of the pain points they faced in their day-to-day work. Suddenly, the layer that existed between myself and the user was virtually eliminated. The problems that we at Informed K12 aimed to tackle became clear to me, as well as the impact we have, and could be making. Having this understanding, I feel a greater sense of investment in my work.

I’m challenged to think and question why.

When I joined my previous company, it seemed as though most of the decisions around architecture and engineering processes were made before me and set in stone. There was already an existing way of doing things, and I did not have much context as to how or why these processes came to be. Additionally, at larger companies, there can be great deterrents for initiating change. Even if one had a new idea and thought, “Why don’t we try this way?” seeing that change implemented can be an extraordinarily difficult feat. There are several layers of management and decision-making entities making any change slow to propagate.

My experience at Informed K12 has been very different — process is an ongoing discussion. There are constant conversations around how we can continue to improve, whether it be the architecture of our codebase, or various processes we have around meetings and interviews. The engineers at Informed K12 are extremely open to new ideas, and are constantly thinking of ways in which things could be improved — there is never a sense of “settling.” As a new engineer, it’s exciting for me to be able to have a say, and take part in these major discussions. I feel my mind challenged in a way it’s never been challenged before. For example, a recent discussion we had in our team was around our code review process. Code review, while extremely vital to any engineering team process, was not something I had ever stopped to think critically about. However, this discussion sparked questions like, “How do we give good feedback during code review?”, “How much time should we be spending?”, “What is the purpose of code review?”, “How can we improve our code review process?”

In these first few months at Informed K12, more than ever before, I have found myself thinking critically, and asking, “Why?”

“How am I approaching this?”

“What is my opinion about this?

“Why do I think this way?”

These questions probed at my own intentionality (or at times, lack-of). Now I find myself being more mindful and conscious of what my thoughts are, what actions I take, and what words I use to communicate with others.

In Conclusion

By nature and sheer-size, engineering at a large company and a startup is going to be a totally different experience. Coming from a large company, there’s so much about Informed K12 that was a culture shock to me.

Coming from a place where I felt as though my voice didn’t have much weight, one of my greatest challenges at Informed K12 has been finding my voice, and leveraging opportunities I have to speak out. Additionally, with a significantly smaller team comes a greater sense of ownership and responsibility. It’s not possible to hide in the crowds of people. There’s greater recognition and visibility of the work you do. This can be gratifying on one hand, and intimidating on the other.

From my experiences at two vastly different companies, I’ve come to realize that with every company, there is always going to be a unique set of challenges. Similarly, with every individual person, there is going to be a unique set of challenges they are happy to accept. The challenges I faced at my previous workplace were challenges I did not want to accept — I struggled with how difficult it was to see the bigger picture, and how compartmentalized my work felt. I felt frustrated by the layers of decision-making entities, and how things move slowly. However, in a similar vein, others may feel unwilling to accept the challenges that come with working at Informed K12. They may dislike being in a fast-paced environment, dealing with change, or having to be aware of what’s happening outside of engineering; Maybe they prefer not to be involved in discussions around process, or decision-making. Personally, these challenges I face at Informed K12 are challenges I am happy to accept!

Coming from a large company, I had some reservations about working at a startup, but four months in, I can confidently say that moving to Informed K12 has been one of the best career decisions I have made. I feel challenged in a positive way, and most important to me, I find meaning in the work I do. I am excited to keep learning and growing.


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