Startup Career Transition: A Software Engineer’s Checklist

Kota Kubo
7 min readOct 3, 2023

More and more people have been moving to startups in recent years. At the same time, we hear that not a few people are wondering about joining a startup. I have created a checklist that you can refer to when joining a startup. This checklist is based on my experience working at a large tech company, and the knowledge I have gained from checking the match between many software engineers and Ubie.

A checklist to see if you are a good fit for a startup

First of all, is your own preference suitable for a startup? If this is not yes, you will not be able to show your value at any startup, which is undesirable for both you and the company.

Can you enjoy working in uncertainty?

Uncertainty is inherent in startups. Rapidly growing startups may appear perfect on the surface. However, there are many hard things and pivots behind the scene. In Ubie’s case, the focus of the business has shifted from B2C->SaaS(SMB)->SaaS(Enterprise) since the beginning of the company. Occasionally, engineers had to take on roles they did not excel in and learn new technologies. In the early years, even ML engineers wrote production code for applications. Working in a startup requires the mindset to enjoy and overcome these uncertainties.

Can you accept that you cannot always apply best practices?

Many engineers value keeping up with the latest technology and implementing it as best practices at their work in their careers. However, this might not be possible for many reasons in startups. Especially in the early stages of a startup, even if you create a Minimum Viable Product, there are situations where it is uncertain whether the functionality and sometimes even the product itself will continue to be alive.

Rather than the latest technology or cleaner codes, it is often more important to increase the speed of delivery and get out of an uncertain situation to verify the product.

Are you prepared to solve technical problems that are not your specialty?

The choice of which technology stack to use should be dictated by business strategy and tactics. Even a middle-sized startup may make a pivot, leading to a change of the technology stack. If you are more motivated to use a particular technology than to grow the product, joining a startup is unsuitable.

A checklist for choosing the right startup for you

Once the first checklist is all yes, the next step is to check what kind of startup is appropriate for you. The reality of a startup differs greatly depending on its stage and culture. If this matching does not go well, showing your value is not possible either.

Are you comfortable with the phase the startup is in?

This section will show you the features of the environment in each of the startup’s growth phases from the engineers’ point of view.

Seed & early stages

It is the company’s early days, and it has only a few to 20 people. They have to verify customers’ needs quickly to aim for PMF (Product Market Fit). Startups often have to pivot in this phase, and the technology stack tends to change. Therefore, engineers who want to persist in a particular technology are not a good fit.

In Ubie, we also shifted its platform to the web relatively early, although native app development was the mainstream. Even in web development, front-end and back-end development needs may change monthly, depending on the business and system architecture requirements. These are phases in which engineers need to have a wide range of development skills to respond to such fluid needs.

Growth stage

This is when the PMF is achieved at a certain level, and the service is expanding. User requests and demands for new feature development increase dramatically. As a result of repeated various testing, their MVP service should have been carrying technical debt, and the development speed may be slowing down. In this phase, technical skills to refactor appropriately, speedy response, and fast delivery are required for developers.

Later stage

At this stage, business concerns have been addressed, and growth is guaranteed with additional investments. As the key technology stack becomes more apparent, some companies hire specialists with specific technology experience. In this phase, engineers who want to bet on a particular technology may be a good match.

Is the issue worth your time and effort?

Especially for those who join a startup in the seed or middle phase, when the exit is not yet in sight, it is essential to be able to focus all your energy on the issues that the startup is facing. For a startup subject to repeated pivots, how to solve the problem is also changing rapidly. Therefore, if you are attracted to the “how” and not the issue itself, your motivation will decrease drastically. Thus, sympathy for the issue is essential.

Is there enough data to make use of your skills?

One point that is often missed is the amount of data accumulated. Many companies hire ML engineers, data scientists, and data engineers nowadays. However, these positions cannot provide value without a certain amount of data. Ubie makes heavy use of machine learning in its services, but there was only one ML engineer and one data engineer in the early years. On the other hand, there were about 15 engineers for web development. From this, you might understand that it is difficult for these positions to perform when data is scarce, even in companies that develop ML products.

Does the startup have its tech culture?

Investments in engineering are becoming more common in tech startups, but sometimes this is not the case. We cannot make Mid-to-long-term decisions about engineering and software without a tech culture. Thereby, continuous development of services becomes increasingly tough, and they cannot make a decision that incurs engineering costs.

When assessing startups as a candidate, you can check the following depending on their stage;

Early stage: Whether there is a board member who understands the technology. Or whether you are confident in your ability to educate them about the technology.

Middle and Later stage: Whether the technology stack has been updated since the earlier phase. Or whether it is taking too much time to develop a few features (indicates too much debt accumulated.)

Are there any talented engineers besides you?

It is also essential whether the startup already has skillful engineers. Of course, there are advantages such as speeding up a business or improving development stability. Even more significant is that talents attract talents, which attract even more excellent engineers. This creates a positive growth cycle for the engineering team. Having such engineers will also benefit other engineers in the team. If you do not already have such engineers, I recommend that you bring them by yourself and transform your organization.

Will the startup pay you enough relative to the market average?

Of course, compensation, including stock options, varies depending on the company’s approach. However, in today’s seller’s market for engineers, if the company’s offer is well below the market average, likely, the company is not investing in engineering. In Japan, although it is difficult to match the compensation levels of foreign companies such as FAANG, most startups seem to offer salaries at the same level of large software and web services companies. As a side note, since startups in the seed phase cannot pay compensation in cash, it is common to set a high percentage of stock options.

Can you love the team from the bottom of your heart?

Finally, do you think you can love your future team members at your heart? Personally, I think this is the most important point. There is a great deal of uncertainty about whether you will get what you want from joining a startup, and unforeseen circumstances happen. Paul Graham, a co-founder of Y Combinator, also asserts that even Google had its worst times, and every startup comes at its own time. When business growth stops or a crucial risk arises. If you don’t love your people at those worst times, you will not survive the trial.

In terms of matching, the most effective way to check is to ask them how they have been making business and technology decisions and to see their reactions when you express your ideas. Before the Corona Disaster, we created opportunities for people to talk about their true feelings in situations different from the selection process, such as lunches and drinking parties, to have them confirm a match. Another way is to check the company’s “Value.” Although it may not always reflect the company’s internal situation, the Value shows each company’s uniqueness. Some companies are working to match the Value with the company’s inside story for utilizing it in hiring and internal communication.


We have discussed two points: whether you yourself are a good fit for a startup and which startup you should select. As an engineer, I hope that more and more talented engineers will join startups and work in new growing-up industries in the future. I wish this article could help it.

We’re Hiring!

Ubie is hiring Software Engineers. We are in the middle phase and are at the stage of leveraging our technology to expand our business. We are looking for people who wants to create the future of healthcare together, so if you are interested, please feel free to contact us for a casual interview.

Hiring Deck

Ubie Global Team — We Are Hiring

I also welcome your messages on LinkedIn!

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