A problem in search of a solution: A Q&A with one of Assembled’s early engineers
Assembled just hit a significant milestone: 100 employees. In honor of the company’s journey from three Stripe alums in 2018 to triple digits in headcount six years later, we’re spotlighting early hires and the unique paths they’ve created for themselves at Assembled. You can find all their stories here.
Neel Kapse is an Engineering Manager who joined the company in 2020 as its eighth employee. In this interview, he shares how his initial call with Assembled’s CEO was just for interview practice, what’s changed and stayed the same as headcount has grown by more than 10×, and why you have to address your insecurities to become an effective leader. His answers have been edited for clarity and concision.
Q. Neel, how did you end up working at Assembled?
A. Before Assembled, I was at a startup that was doing reasonably well, but I started to find the culture to be quite unpleasant. I started looking for a place with a better culture where I could have a bigger impact given my experience.
Ryan (Wang, co-founder and CEO) reached out to me via a recruiting service that AngelList used to have. When I first saw his message, I thought, customer support sounds super boring, but I’ll take the call for interview practice.
When I chatted with Ryan, I realized two things: 1. Ryan is an interesting, intelligent person that I wanted to work with, and 2. It was a company that had clearly found product market fit in an unsexy space — which is a great quality to have.
I was coming out of a company that could afford to treat employees poorly because it was in a very sexy space, but I didn’t feel like the business was super sound. Hearing about Assembled, I immediately felt like, this isn’t just a technology looking for a problem — it’s a problem looking for a solution.
Another big selling point for me was Assembled’s transparency culture, which our co-founders adopted from their time at Stripe. That really resonated with me because I wanted an opportunity to operate outside of just my engineering role — I wanted to be in tune with what was happening in other parts of the company.
The final piece that sealed the deal was that I spoke to everyone at the company. There were seven people at the time. And every one of them was excited to work hard and get better at all the things they were doing. That growth mindset culture aligned with how I work, so I decided to join.
Q. Does that mean you were the eighth employee?
A. Yes, I think so.
Q. Growing from a company of eight after you joined to a company of 100 now, what’s been the most striking part of that transition from your perspective?
A. When you use the word "striking," two things come to mind: what has changed the most and what has surprisingly stayed the same.
The biggest change is how information gets shared across the company. As an engineer back then, I was in tune with all the company’s happenings because there were only eight of us. I would read every single document about a big prospect, which were few and far between. Today, as an Engineering Manager, I simply don’t have the time to keep up with the dozens of deals we’re working on every day. This change in scale has been significant.
This shift has required adjustments, especially in ensuring that engineers stay connected with our customers despite the company’s growth and the division of functions across multiple departments. The old style of everyone knowing everything doesn’t exist anymore.
What hasn't changed is the growth-oriented mindset. Everyone at Assembled still pushes to make improvements and points out even small issues, whether it's meeting structure, a minor thing in the codebase, or a design element of our product. These things still come up in our feedback channels and team meetings. I still see everyone's excitement and drive to make improvements, which has remained consistent throughout our growth.
Q. In your early days at Assembled, what were some of the most challenging technical problems you faced?
A. In my first year at Assembled, two major technical challenges stood out. One was the stability and consistency of our Google Calendar integration. The other was rebuilding our staffing timeline, our core scheduling functionality, with a small team of about two and a half to three people.
The Google Calendar integration was particularly challenging because we were constrained by the bounds of Google Calendar’s system. Our integration provided a lot of functionality, syncing with Google Calendar in two directions. We even had two different types of integrations to meet the varied needs of our customers. This feature was very popular and often a deciding factor for customers choosing us over competitors, so it was crucial to get it right and fix any shortcomings.
The staffing timeline project was another significant technical challenge. Imagine any calendar app you've used; it's optimized for one person's calendar. Now, imagine optimizing a system like that for a thousand people at once. That's the staffing timeline problem. With just three people working on it, we didn't have the luxury of rebuilding without a solid reason. We had to be very creative and intentional in solving the problem of scheduling effectively in bulk. This project was essential because our customers were scaling up, and we needed to support workforce managers with much larger teams than we had before.
Q. How do those challenges compare to the challenges you face now, given that there are more resources but also bigger ambitions?
A. In many ways, the staffing timeline project marked the beginning of a new era of technical challenges, and those challenges still exist to some extent. What's changed now is that Assembled is setting some of the future directions in the workforce management space, especially on my team.
Previously, our challenges were more straightforward — if we built a certain feature, it was clear it would be useful. Now, we're dealing with enterprises that have unique problems with no existing solutions in the market. Our challenges are not just about achieving feature parity but about anticipating how the support space is evolving.
We’re looking at advancements like large language models and omni-routing from Salesforce Service Cloud, which are reshaping workforce management. Our challenges now involve figuring out how to operate in this future landscape and support increasingly large enterprises.
Q. What do you feel has been your most significant contribution to Assembled?
A. That's a tricky one. I've contributed in so many different ways, from writing code to leading and managing teams. If I had to highlight one thing, it would be my work driving our vision around scheduling, especially scheduling at scale.
One significant feature that exemplifies this vision is the Schedule Change Requests, originally built for Robinhood. They needed a way to keep their team efficient while giving agents the flexibility that’s part of their culture. This feature allows agents to request schedule changes, empowering them while giving workforce managers confidence that support needs are still met. It strikes a balance between team efficiency and agent satisfaction.
A small team of about three people built this feature in roughly three months. It's been widely used and adapted for broader purposes than we initially intended. The ideation and development of such impactful features are probably my biggest contributions to Assembled.
Q. You mentioned mentorship. Is this the first job where you've taken on that role in your career?
A. Yes, this is the first job where I've taken on management in my career. I originally got into it out of an interest in product design and vision rather than people management, but I’ve found the people management part to be quite enriching. It took a lot of learning, but I’m starting to figure it out and feel I’ve been able to do it effectively.
Q. What have you learned about yourself in that process?
A. I've learned a lot about myself, particularly with the help of a great coach early on. One of the biggest things was coming to grips with my own insecurities and understanding how they were affecting my work. I found some insecurities holding me back in various interactions, such as when talking to engineers on the team, or during conversations with other leaders. Addressing these insecurities has made me a stronger leader and a happier person overall.
Q. And probably well-suited to help others suss that out in their own careers?
A. For sure. Many of the engineers I work with take on roles beyond just engineering; we ask them to be their own product managers. A big part of training them is helping them get comfortable with the ambiguity that comes with non-engineering roles. When you're good at a technical role, you can be precise and rarely wrong. But in leadership or product management, you have to make more bets. Helping people get comfortable with that has been a significant part of my role.
Q. What advice would you give to new engineers joining the team?
A. For new engineers joining Assembled, I have a couple of key pieces of advice. The biggest one is what we call "bias to action" or "get on the plane" as a cultural value. It's also been described as "ask for forgiveness, not permission." Essentially, it means that just going out and doing something because you think it's a good idea is often the best way to learn what the best idea is.
There's a principle called Cunningham's Law, which states that the fastest way to get the correct answer on the internet is to post the incorrect answer. This is why Wikipedia works — people go to great lengths to correct misinformation. The same principle applies in the workplace. If you ask someone a question, they might not respond immediately, but if you post an incorrect answer or an opinion that's wrong, people will quickly correct you. This approach has been very effective for me, and I encourage engineers to adopt it.
On a more tactical level, let's say you're an engineer working on a piece of code. Often, new engineers will try their best to build something and then show it to others for feedback. Instead, I push people to share their plans early on. If you have an idea, even if it's just a sentence or an assumption informing your work, post that assumption in our Slack channel and let people oppose it. You don't need to push people to do anything — just say, "Hey, this is what I think and what I'm about to do." Senior engineers, in particular, are encouraged to engage and provide feedback. This model is great for moving fast and doing a good job.
Q. How do you inspire creative problem solving in yourself and your team?
A. That's a good question, especially challenging as the company scales up quickly because the constraints and rules change frequently. But it's something I've had to do, so here's my take on it.
One thing that has helped me a lot in being creative is optimism and confidence that we can find amazing solutions. This is easier when working with a great team, and our design team has made this very easy for me. I've worked with fantastic designers like Steph, Shannon, and Anna, who allow me to be bold and creative in my proposals. In concert, we come up with innovative, strong solutions.
In more established, larger companies, creativity and problem-solving can be stifled, but at Assembled, we maintain a bit of bravado. We’re a tiny team serving much larger customers, but we’re skilled and work well together. This mindset helps us brainstorm and come up with creative solutions.
For example, our shift patterns feature could have been a simple copy of what competitors did. Instead, we started from first principles, analyzed what others did, assessed our customers' needs, and worked closely with them to get feedback on various designs. We built a system that was uniquely our own and, I believe, does the job better than our competitors.
Q. How do you prioritize and focus when there's so much work to do? How do you encourage your team to focus on the right things?
A. Focus starts with recognizing that there's more work than you can handle. Newer folks often think they have to do everything, but it's crucial to understand that you can't. Our CEO, Ryan, embodies this well — he always has just two main focuses and lets others handle the rest or lets some fires burn. This approach is necessary given the breadth of our responsibilities and resources.
Prioritizing involves deeply understanding our company’s current strategy and how decisions affect that strategy. If a particular feature is key to our strategy, it gets prioritized. If hitting a deadline is more important than meeting our usual quality bar, we focus on the deadline first. This is always a nuanced discussion.
Additionally, people concerns are often as important as the company strategy. If a piece of work will make the team miserable, it might be better to give them space to do other things first. Balancing these factors is a big part of prioritization.
There's a quote from Jony Ive, originally from Steve Jobs, about focus: "Focus means you wake up in the morning and every bone in your body tells you to work on something, and then you work on something else because it's more important." This sums up how I think about focus and how I encourage my team to prioritize the most important tasks.
Q. Is there anything you do outside of work that makes you better at your job?
A. Yes, lots of things! The most recent is playing a card game called Android: Netrunner, which involves a lot of reading people and bluffing. This has helped me improve my understanding of people, a crucial part of my job today. Unlike chess, which I played competitively as a child and is all about analysis, Netrunner requires understanding how others think and what they care about.
Q. What do you look for when interviewing engineering candidates?
A. I prioritize attitude over skills when interviewing engineering candidates. I look for people I’m excited to work with, who will push to do a good job, and who understand that doing a good job often involves more than just writing code. It includes working well with others, figuring out what needs to be built, and understanding customer needs.
I also look for a growth mindset. I want to work with people who can take and give feedback well. Assembled is an environment with lots of smart people who have a lot to teach, and we need people who will make the most of that opportunity to learn and grow. While skills are important, attitude is the key factor I look for.
Q. What are you most excited about in terms of Assembled's future?
A. I’m most excited about the opportunities in our space, historically controlled by legacy players whose time seems to be ending. With the advent of AI, the space is changing rapidly. We are one of the very few companies, perhaps the only one, with a background in workforce management that's nimble enough to be part of the AI revolution. I'm excited to see where we go and how we shape the future of workforce management.
Assembled is still growing! Check out our open roles.
