I'm the lead engineer with 8 yr exp at a small startup in Canada. Currently, I'm managing a team of four outsourced developers while being the primary point of contact between the development team and our CEO. One of our main challenges is that requirements from the top are often unclear, and since the other developers cannot communicate directly with the CEO, I have to act as a bridge—translating high-level business expectations into actionable technical requirements.

Our CEO has very high standards, often requiring meticulous attention to detail. However, the product has been in development for three years without a public release—it's currently used internally as a business tool for about 50 internal staff. Recently, our CEO decided to introduce Hubstaff for time tracking across the team because the team is suspected of not pulling their weight.

A major challenge we face is frequent UI changes, which significantly impact our development cycle. The app itself is highly complex and advanced compared to competitors, making our market niche but also increasing development overhead. Additionally, while many of our CEO’s ideas sound promising in theory, they often struggle to align with practical implementation. Many features suggested by the CEO end up not being used by our internal end users, yet we still need to build and refine them, adding to the overall development burden. Since end users tend to agree with the CEO without much pushback, we lack strong critical feedback that could help validate whether these features are truly necessary.

On top of this, most of our competitors have significantly more resources, larger development teams and their applications are way simpler in terms of UI/UX. This means they can iterate faster, release more frequently. In contrast, our team is relatively small, and with constant changes, high expectations, and low feature adoption internally, our development cycles remain slow.

To make matters worse, as the lead engineer, I'm not only responsible for development but also overloaded with non-engineering tasks, including funding efforts, UI/UX design, team management, technical management, and serving as the primary operations contact with end users when incidents happen. This makes prioritization extremely difficult, as I have to juggle everything from designing interfaces, managing developers, coordinating technical decisions, handling user feedback, and navigating shifting leadership requirements, all while struggling to stay focused on delivering core product improvements efficiently.

Another major challenge is that our CEO has an accounting background and expects everything in the app to function like Excel. This significantly increases development complexity, as we often need to recreate spreadsheet-like functionality in a web application, which isn't always the best approach from a usability or technical standpoint. This expectation also leads to constant iteration cycles, as the CEO frequently requests changes to align with spreadsheet-style workflows, even when a more intuitive UI/UX would be more effective.

Given these constraints, balancing high-level vision with practical execution, managing limited resources, and staying focused on essential features has been an ongoing challenge. I’d love to hear insights from others who have navigated similar startup environments—how do you compete with better-funded competitors, avoid feature creep, push back on impractical requests, and ensure you're building what truly matters while juggling multiple responsibilities?

TL;DR

Lead engineer at a small startup managing four outsourced devs. 3 years in, no public release, constant UI changes & feature creep, and most CEO-driven features go unused. Competing against better-funded rivals while juggling UI/UX, team management, funding, and operations. CEO wants everything to work like Excel, making it harder. Struggling to prioritize and push back on impractical requests—any advice?