Wearing All the Hats: A year into leadership in engineering at a startup

When we think of startup life, we tend to envision ping-pong tables, quick product iterations, and a culture of "move fast and break things." But behind the stereotypes lies a harder, more challenging reality—particularly for engineers who manage teams in environments of fewer than 25 individuals.

Working as a Lead Software Engineer in a small startup, I have been primarily focused on engineering productivity and operational excellence. However, being a Lead Software Engineer involves much more than technical leadership; it takes constant adaptability, a culture of high-trust, and being open to venturing into the unknown.

Productivity Is a Team Sport

Engineering productivity at a startup isn't a matter of writing code quickly or implementing CI pipelines. It’s about establishing systems and workflow that eliminate friction from everyone on the team. That means:

Selecting appropriate abstractions early on (and refactoring when those don't scale)
Automating all that repeats
Maintaining close feedback loops: from deploys to commits, from code reviews to production

Here, operational excellence refers to prioritizing reliability, monitoring, and response to incidents as first-class citizens—on par with feature delivery.

Independent Study and Self-Paced Learning

One of the most enjoyable, yet challenging things about working at a small startup is how frequently you're asked to venture out of your comfort zone, i.e., your core skill set.

I've transitioned from writing infrastructure-as-code to debugging TypeScript in a single afternoon.
I've been the individual onboarding new engineers, along with setting up production alerts on systems that I hadn’t initially developed.
I've used tools I'd never worked with before—figuring them out ad-hoc because they addressed actual issues, right now.

Being able to learn independently and rapidly isn’t a premium ability at a startup. It’s table stakes.

Collaboration Means You Are Extending Yourself

Within a group this small, teamwork doesn’t merely equate to excellent communication—it equates to leaping into others' areas to clear up blockages.

Oftentimes that means:

Pairing up with a data teammate to debug a query you didn’t write
Picking up a UI task even if you are a backend developer
Writing internal documentation because you were the first to discover something

To put it briefly, you don't get to utter, "that’s not my job" in a startup. You respond by saying, “What do we need to deliver?” and then proceed from there.

Operational Excellence Is Not Optional

Small teams are prone to being brought down by tech debt, unreliable deployments, or a single missed alert. That’s why we place a strong emphasis on:

Infrastructure resilience: Rollbacks, retries, fail-safes
Monitoring and observability: You can't fix what you can't measure
Developer experience: Rapid setup, repeatable environments, automated testing

Operational excellence is how you maintain velocity without compromising reliability.

Leading by Example

Being a lead here isn't about driving architecture or code review. It means leading by example with the behaviors that make teams effective:

Being transparent about what you do not know—and how you come to know it
Developing structure without bureaucracy
Maintaining high standards while remaining pragmatic
Remaining focused on business objectives, even when technology is exciting

Leadership at a small startup isn’t a matter of being the smartest in the room—it’s being most reliable, curious, and unblockable.

Last Thoughts

Being a lead engineer in an extremely small startup is perhaps the most demanding and rewarding professional challenge I have ever encountered. You have multiple hats, push your comfort level, and are constantly juggling speed versus sustainability.

You come to appreciate trust over hierarchy, results over output, and curiosity over certainty.

You'll find startup life highly rewarding if you're a person who thrives on ambiguity, learns quickest, and loves creating systems that enable others.