This is Hamamoto from TIMEWELL Inc.
Two Engineers. Eight Months. One Platform That Does Everything.
TIMEWELL BASE handles event planning, hosting, customer management, email broadcasting, CRM, and AI — all in a single application. Most people would assume a team of dozens built it over years. The actual team was two engineers. The actual timeline was eight months.
The engineer who made that possible is Kazuki Naito, co-founder and CTO of TIMEWELL. This interview covers how that happened — and what his approach to engineering, team-building, and work itself looks like from the inside.
Name: Kazuki Naito Title: Co-founder and CTO — TIMEWELL Inc.
Background: Born in Tokyo. Graduated from Shibaura Institute of Technology. Joined NTT Advanced Technology as a new graduate, where he worked on cloud-based SI. Later became technical lead and Scrum Master for a product company's new service development division, building POS services and digital signage products. Personal projects include OSS contributions, an industry-specific job change site at 500K peak monthly page views, and various pro bono development engagements. Currently focused on the design, development, and operation of TIMEWELL's services.
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An Engineer Who Earned His Skills Outside Work Hours
— Let's start with your introduction.
I'm Kazuki Naito. I joined TIMEWELL as CTO and engineer at founding. My background includes cloud-based SI work at NTT Advanced Technology and technical lead and Scrum Master roles at a product company.
— Early in your career, you did a significant amount of pro bono engineering work. What was driving that?
The goal was to build enough experience to lead product development end-to-end. I started in contract development, and I realized quickly that pure contract work wasn't giving me what I needed — the client relationship is mediated through contracts and layers of organization, so you're always at a remove from whether the product actually landed well. You don't feel it.
I wanted the experience of building something, shipping it, and having users feel it directly. But getting paid side work as a junior engineer with no product track record is difficult. My solution: offer to work for free. Several companies accepted, and I got the reps I was looking for. That was the foundation.
— What were you like as a student?
Honestly, I was low-key. I was more inclined to keep things quiet than to push myself. But as graduation approached, I started asking what I actually cared about. Robotics was an interest, so I went to a university where I could study it. Then I realized I was genuinely not suited for hardware — I couldn't build a miniature car. So I pivoted to software.
What I found: software gives you instant gratification. A laptop is all you need. You can start in five minutes and have something working in five minutes. The accessibility of it resonated with me deeply. My first project was a to-do app — the most standard onramp in the industry. Took about two months as a part-time student project. I was amazed when it worked. I could probably build the same thing in ten minutes now, but that first completion was real.
— What made you commit to software as a career rather than just a skill?
My family's unofficial motto is something like "work to survive, but don't enjoy it." I looked at that and thought: that's not how I want to spend forty years. I wanted to find something I was good at and get credited for doing it well.
Software was the intersection. I was good at it — when my classmates were struggling with programming assignments, I was genuinely enjoying them. And I'd already demonstrated to myself that I could stick with it. Choosing what you're actually suited to isn't idealism; it's practical.
TIMEWELL BASE: How a Platform Gets Built at Startup Speed
— How did TIMEWELL BASE start?
The vision for an event management application predates TIMEWELL as a company. CEO Hamamoto had been talking about eliminating the friction in event management since well before TIMEWELL ASSISTANT launched — probably since 2022 or earlier.
We actually built a first version under the name "Rakuraku Eventing" — a lightweight prototype. But we ended up pivoting to TIMEWELL ASSISTANT, which was the immediate business priority. The event pain points didn't go away, though. Customer interviews kept confirming strong demand. So we came back to the problem and built TIMEWELL BASE.
— What was different about TIMEWELL BASE versus the first attempt?
The first version was narrow. It implemented a subset of features that already existed in the market — there wasn't a clear reason for it to exist. I was aware of that even at the time.
TIMEWELL BASE is designed around a different premise: everything related to running an event should be possible within a single application without switching between tools. Event planning, ticketing, attendee management, bulk email, CRM-style relationship tracking, AI integration — all of it, in one product. That's genuinely not common. Most companies offer one piece of that stack.
The scope is substantial. In a pre-AI era, a product this size would require a team of tens of engineers. What AI-assisted development has done is compress that. Two engineers moved at a speed that wouldn't have been possible five years ago.
— What was hardest about the eight months?
Feature scope at the beginning. We wanted to do everything, which meant we had to make real decisions about what to ship and what to hold. There are features that are implemented but not yet released — held back because the priority was getting the core value out first.
One technically challenging piece we eventually deferred: automatic Zoom meeting recording with summarization, implemented at low cost. We worked on it, found a workable approach, but ultimately didn't release it. The tension between "could we do this" and "should we do this now" was present throughout.
I don't frame these as failures. Every deferred feature was a decision to maximize the value we actually delivered. That aligns with how the business side thinks about it, so there wasn't real conflict.
"Not a 1-on-1 — a Chat Session": How the CTO Connects with Non-Engineering Staff
— As CTO, how do you maintain relationships with the broader TIMEWELL team — not just engineering?
I do a monthly conversation with the assistant operations team. I deliberately don't call it a "1-on-1" — that phrase has a slightly formal, evaluative connotation that I wanted to avoid. I call them "chat sessions" (oshanashikai). The purpose is to hear what people are finding difficult.
Problems don't get solved in one conversation. It takes sustained contact for someone to recognize me as a person they can actually bring things to. The monthly cadence is about building that recognition gradually.
I'm also lightly involved in customer success. I check in regularly on whether there's anything the engineering team can do to address client requests. So I end up talking with a wider range of people than you might expect for an engineering-focused role.
— Why direct conversation instead of a feedback form?
Most people can't write their concerns into a form. I'm one of those people. If someone says "just let me know if anything comes up," I won't say anything. People's issues surface through conversation, not through prompts.
My personality helps here. I'm not the stereotypical quiet-in-the-corner engineer — I'm pretty approachable. I want people to know that when they're stuck, they can come to me for a casual conversation, not just a formal request. That requires actually being present in those conversations over time.
— It sounds like a full schedule. How's the TIMEWELL aspect of it — the time-well-spent part?
Genuinely good. My wife goes into an office, so I'm the one at home. I cook lunch. I handle daycare pickup and drop-off. There are occasional nights where I miss reading bedtime stories, but reading to my child is normally my thing, and we eat together as a family regularly. Busy periods come and go, but structurally, I have real flexibility to prioritize family. That's not incidental — it's part of why I chose this path.
What came through across the whole conversation was the combination of technical ambition and interpersonal care. Naito is the person who built a complex platform at speed and also designed a monthly check-in structure because he was worried about who the other assistants were turning to with their problems. The two things fit together — which is probably what a CTO who cares about wellbeing, not just product, actually looks like.