【Job Change】From an SIer to a Web Startup: My Engineering Job-Change Story!

As of September 2022 I have changed jobs twice. Here I look back at the first move — from an SIer to a web startup — what went well, and what I wish I had done beforehand. I hope it helps if you are deciding whether to move (this is not a “you should quit” pitch)!

Introduction

I left the large SIer I joined as a new grad in April 2017 at the end of March 2020, and moved to a web startup. It was my first job change, and I still remember how long it took to actually do it. I am genuinely glad I moved — and I also think I should have decided and acted sooner.

Why I wanted to leave

Because I was at a large company, my work was already tilting toward management and planning and aligning with the customer, more than implementation. Even as a junior, the layer of the work kept getting higher while I did not feel my skills growing. I started to worry that my market value was dropping. The project I was on was also extremely mission-critical. We could not use OSS, cloud, or widely used frameworks. The stack was old, and we leaned heavily on in-house middleware. People moved around a lot, and it was hard to do the work I actually wanted.

That is where I was. I spent a few months of my third year going back and forth, then decided to change jobs to build skills and raise my market value. The three axes I used:

• I wanted implementation and hands-on skills
• I wanted to work with OSS, frameworks, and other widely used tech
• I wanted a smaller company (under 100 people)

I got two offers and picked the company using those axes. Looking back, I think the axes and the decision were right. I chose a smaller company because I figured I would be more likely to get assigned to work I actually wanted to do.

It took a long time to actually leave

I hesitated for several months. Two reasons, mainly:

• I was at a large, well-known company
• I was on a large, well-known project

Both the company and the project had a lot of name recognition. As a new grad I did not really know which companies were good, so I aimed for a big one and worked hard to get in. Letting that go felt scary. In the sense of “work that holds society up,” I might never touch that scale again. I think large companies do give you a better shot at socially large work, so if that matches your values, it can be a good place (this is just my view, and a tendency).

For me, raising my market value felt more important, so I decided to leave. Even if you only know that one company and get good at its way of working, that skill is not portable if you need to move later. If you raise your value, you can still join a large company and a large project later.

Agents

I signed up for others too, but these are the ones I used most!

Levtech Career

This is the mid-career hiring arm of Levtech, an IT-specialist agency. I also used the IT desks at other large agencies, but Levtech Career was in a different league — much more specialized, and the roles they sent were a better fit. If you are considering a mid-career move in IT, I would just start there! Friends and colleagues say the same about Levtech Freelance and Levtech Rookie (new grads). Levtech as a whole is a strong recommendation!

Wantedly

https://www.wantedly.com/

More of a job board than an agency. You post a profile, apply to companies yourself, and get scouted. Interview scheduling happens in Wantedly chat.

How the job search went

Schedule

I started applying and interviewing in February 2020 and had an offer from the company I wanted in early March (about one month of activity). I had a lot of leftover PTO, so I told them I was leaving before I had the next job locked in. I would not recommend that if you do not have PTO. For a mid-career move, companies often wait from offer to acceptance, so it is usually better to tell them you are leaving after you have the next role.

What actually happened

I applied to about eight companies and got two offers. I expected it to be hard, but I got fewer offers than I thought. I was not from a web background and did not know frameworks, but overall it was not enough skill. That is also why I was glad I moved when I did.

Between the two offers, I picked the place that used OSS frameworks and looked busy in a good way. Both paid the same as my previous job — exactly the same amount.

What to do before you start looking

For engineers, certifications do not count for much. Interviewers look at what you have done in production, how you learn day to day, and what you publish — basically skill and a learning habit. I have been on the interviewer side at my next company, and most of my questions were “what can you do, and what does it look like you could do soon.”

Deliver results at work

The best path is to spend time learning what you are already doing at work, then put it back into the job until it becomes real skill. Nothing beats production experience. Grow in the work itself and ship results.

Put work on GitHub

People will look at GitHub. It does not have to be large. Push something regularly, be able to talk about it, and keep the contribution graph green.

Sign up for agents and services early

As soon as you even start thinking about a move, register with an agent. If you try to switch on a short timeline, you can panic and join a company you did not actually want. Registration is free, so do it early. You might get a good scout.

Also sign up for sites that score your skill, like AtCoder or Paiza, and keep them updated. You can get better scouts while you get stronger.

Build a specialty

Build a specialty in the area you actually want to own (like Spring on the backend). It is fine if it is only relatively strong for you. Organize the technical story so you can talk about it in interviews.

Takeaways

Salary matters, but especially early in your career, experience and growth matter more! If you want to hear more, use the contact form or DM me on social!

How mid-career hiring differs from new-grad hiring

New grad: potential — what you might be able to do
Mid-career: they look at skill (juniors still get some potential credit) — what you can do now

Mid-career hiring is more results-based than new-grad hiring. So it matters to ship results day to day and be ready to show them.

SIer vs. web startup

They are both IT companies, but the culture is quite different. This is from the projects I was on.

At an SIer, the organization is already built. Policies, internal systems, and standard documents are already there. They often build their own middleware and hardware, so you use in-house products and support is fast. You often work on large, public-facing systems, so security and mission-criticality tend to be high, and the stack tends to be older.

At a web startup, policies are thinner. You gather opinions and keep building them. You mostly build with OSS and cloud. The business is smaller, so systems tend to be small or medium — but you can own a whole system.

The startup pace and the “we build it ourselves” style fit me well. Being able to touch the whole system, because it is not huge, is also attractive when you are junior.

What actually mattered

Looking back from 2022 (I have now gone freelance on a second move), the decision I made on that first career change still looks right, and so do the criteria. I would add: check what communication tools they use, and whether communication is actually active. At the web startup we used Slack and were fully remote, and it was easy to ask questions and jump on a call. That was one reason I grew.

My salary barely went up on that first move. The goal was to build skill I could cash in two or three years later and raise my market value. That also looks right now (as a freelancer my pay has gone up a lot). You will worry about money. In your 20s, I think it is more important to pick the place where you will actually get stronger, rather than the next paycheck!