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Size Doesn’t Matter: Why I Moved From Big Company to Small Startup with David Yu, Director of Engineering (Part 2)


In the first part of our interview with David Yu, he spoke about his decision to leave a large, established company and the process he went through to join Kloudless. In Part 2, David highlights work culture, management, and other challenges as he transitions from big company to small startup.

What do you like most about Kloudless’ work culture?

The flexible work hours and Work From Home (WFH) policy! I love and appreciate that Kloudless fosters an environment of trust. Due to the internal tracking and the pre-approval of remote work, our team members don’t treat WFH days as a vacation day; employees are still responsive when it comes to getting work done. We treat this policy as a strategic productivity tool, and it exhibits how autonomous we are at Kloudless.

What were some of the challenges of transitioning from a large company to a startup?

I believe startup employees generally tackle a diverse set of responsibilities, and the company is still small. It’s common for startups to adopt an “all hands on deck” culture. Managers at large companies mainly need to put our focus on management, which includes people and projects. But at Kloudless, we not only manage, but are also hands-on with coding. Working for a smaller company provides greater exposure to different job functions. Everyone wears multiple hats, which is common in the startup software industry.

Was there anything that took you awhile to get used to? Or anything that you’re still getting used to?

The balance between coding and people management is something I’m still getting used to. In my previous role, I coded less when I became a manager and spent more time managing people and overseeing projects. After joining Kloudless, we needed a hands-on Director of Engineering, so I had to brush up on my coding skills. The code base at Kloudless is quite complicated. I’ve spent a good amount of time learning and working in it.

After I grasped the technical side of things, I diverted my focus to management. At Kloudless, we take employee performance evaluations seriously. Managers prepare extensively before conducting evaluations on a quarterly basis. Since we’re expecting more engineers to join the company, I have even more weekly 1:1 meetings than before. I wish I had more hours in the day to handle meetings, project management, and coding.

Now that you’ve been leading the engineering team in Taipei for a while, how would you describe the engineering processes at Kloudless?

Early stage startups look to scale their team and organizational structure. Our products are in their early stages, unlike the stable products of larger companies. This means that progression can be faster than expected, and decisions are made quickly to find the right direction that meet our clients’ needs. At Kloudless, we have quarterly OKRs and often make changes. This is something that’s different from my previous experience at big companies.

Finding the right go-to-market strategy is always a top priority for startups, which can be both exciting and challenging for the growing team. I believe the type of person that joins a startup must have the courage and mindset to embrace change. It can be frustrating when we encounter challenges, but that’s what the startup life is all about, right?

How are the processes different from those at your old company?

At my previous company, the products were mature and stable. We usually were given the big picture at the beginning of the year, discussed and confirmed features every 3-4 months, and deployed 3 to 4 versions of the software a year. There is a fixed execution process, so we only need to follow the process version after version. The product trends were also stable and predictable!

How do the challenges of a startup compare to your past challenges at a big company?

Decisions frequently change, and the working hours seem to be longer than before. It can be exhausting when we’re constantly adapting to change, which is why I appreciate the flexible hours we have to promote work life balance.

Moving in a fast pace is essential at startups. Unlike large companies, when we’re feeling unproductive under certain situations, we give our employees flexible time off to take a break and regroup. However in the large companies, you have to be in the office regardless of whether you feel productive or not.

In the past, the work hours and non-work hours are clearly defined at a big company, but at a startup those lines are blurred. I can take time off in the middle of the day or take a break at a coffee shop as I please. So in this case, our work style isn’t clearly defined and can be extremely different and challenging for some people coming from a large company.

How has the flexible work environment impact employee performance?

Startups are not environments that can tolerate laziness because the workload is heavy. The team is small, so it’s obvious when a team member isn’t pulling their weight. Everyone’s collaboration is critical when operating in a small team. Employees at Kloudless take advantage of the WFH policy in a positive way. The team is usually responsive and can be easily reached via Slack when needed.

Our main concern is getting things done on time. Since we conduct quarterly employee performance evaluations, employee contributions are clearly identified to outline the progress that was made in the past few months. Each person’s production capacity has a fixed rhythm and we can safely assume that employee performance should increase overtime as they become more familiar with the professional content and technical skills. But sometimes, we understand that distractions from personal reasons can affect performance and we take that into account.

What is the difference of team management between the two companies?

This 1:1 frequency is extremely high at Kloudless! We have 1:1s every week, but this is good thing. At Trend Micro, Human Resources encouraged managers to do 1:1s with their employees at least once a month, but even then it was mostly impossible. Managers preferred employees coming to them first instead of taking the initiative to reach out. I used to have a 1:1 every one or two months. This was not the ideal, because some employees raised concerns that were brought to my attention too late. As a result, I updated my 1:1’s to a biweekly cadence.

At Trend Micro we conducted annual performance evaluations. At Kloudless, we have weekly 1:1’s, and managers are expected to conduct quarterly performance evaluations. Our goal is to provide employees with specific and constructive feedback. The performance reviews include meticulously detailed items, which requires ample preparation in advance.

I used to supervise 12 direct reports and it was manageable because the workload wasn’t heavy. Currently, I manage eight direct reports, weekly 1:1 meetings, and quarterly performance evaluations. Balancing the technical workload and management well has become a new challenge for me at Kloudless. We’ve been actively searching for an Engineering Manager to help scale out the team.

What are you most proud of accomplishing so far at Kloudless?

Soon after joining Kloudless, I had the opportunity to represent and promote Kloudless at the PyCon Conference in Taipei, as well as several other conferences and Meetups in the area. In the past, I seldom had this opportunity, so this was a new and fun experience for me. I felt great promoting Kloudless to fellow developers and informing them about a startup doing API integrations in Taipei.

In addition to promoting Kloudless at events, I published a hiring post on the Facebook Python Taiwan page, which surprisingly received over a hundred Likes! I felt a great sense of achievement, because my post attracted so much attention and led to a several job applicants.

If you could travel back in time, would you still make the same decision to join Kloudless?

To be honest, this quarter is more exhausting than ever. It has been almost a year since I joined Kloudless, so this question has crossed my mind, “Do I regret leaving my previous company, leaving that stable life I used to have?”

After thinking twice, I would still make the same decision to join Kloudless! As an engineer, I hope to regain my coding abilities since I didn’t get the chance to code much at Trend Micro after becoming a manager. Some things about working at a big company that I don’t miss are the stiff working hours, inefficiency, and the predictability of life. At Kloudless, I no longer concern myself with these things, and the Trend Micro work environment doesn’t interest me anymore.

What are some of your biggest challenges now?

My workload is pretty intense this quarter. The biggest challenge is finding the balance between coding and people management. I have eight 1:1 meetings every week this quarter, which is valuable but very time consuming.

It has been challenging for me to juggle coding, code reviews, writing blog articles, and moving offices. We’re making a company-wide push to generate more content to help our customers. Every engineer is expected to contribute one blog post per week. Our team is also growing quickly, so we have been preparing to move into a new office for months. Designing the ideal office with a team has required much of my attention, but I’m excited to move into our new office!

What do you want to say to the future Klouders?

Kloudless is a unique and energetic U.S.-based startup with a bright future and team members that are easy to get along with. If you’re ready for a challenge and want to work in an open environment, join us! Every member of our team has a voice in the company, and we encourage open communication in our flat organization, which is rare in most Taiwan companies.

What do you do for fun outside of work?

I enjoy watching mystery films or movies that put focus on humanity.  My all time favorite movie is The Dark Knight. The Director put a lot of focus on the characters’ thoughts, intentions, and motivations, which I found entertaining. When I’m spending time with my wife, we like planting on our balcony and watching TV drama series together. My favorite American TV series is House of Cards. My wife and I love POP music, and we used to Karaoke often when we were younger!

Published By

Hannah Su