My Transition From a Large Corporation to an Early-Stage Startup

Problem

Though I’ve been working in a startup for five years now -- loving every second of it -- my entire career before joining my current company was in large enterprises. Many things I took for granted in corporations were simply non-existent in startups, from managing stakeholders to building a team. Also, my experience of transition as an Engineering Leader was vastly different from those transitioning as ICs.

But, let me give you some more context here: I joined as the first engineer on the team. There was a CTO, so effectively it was two of us and we had few data scientists who needed engineering support. I didn’t have a fixed job description or a typical day at work, as at the initial stages I had to roll up my sleeves and do whatever was needed from setting up database servers to troubleshooting infrastructure issues to writing data pipeline code. On top of that, I had to hire and build a team. While for some folks wearing so many hats and dwelling in ambiguity sounded like a total nightmare, for me, it was a realm of unfolding opportunities that helped me hone my skills and grow in my career.

Actions taken

Expanding and honing my skills

To thrive in a startup environment, I had to be a quick learner. For example, I never did anything related to a server setup, yet I rolled up my sleeves and managed to set it up. I had to learn a lot on the fly, but as I would do one-off things, I would also set my sights on the future and consider it an investment into my skills as well as a foundation for other people to build on it.

Many skills I had to acquire or improve were not technical or core to my job at all. In my previous jobs, except interviewing candidates, I never did anything related to hiring, but during the initial days, I had to partly play the role of a technical recruiter and reach out to candidates on various platforms, screen & schedule interviews etc. So, in a short while, my skills broadened beyond typical EM skills one could develop in a large corporation.

Building a team from scratch

Building a team was one of the main objectives and something that I was tremendously excited about. In the earliest days, I depended a great deal on referrals. However, I had to be conscious of a potential bias we all inevitably have and be careful with hiring people who I, or someone I worked with, already knew. People would frequently fall into the trap of recreating a culture that worked well in some other places, but I knew from the start that this startup should nurture its own distinct culture based on its mission and vision.

With a limited budget, I had to hire two types of people: multipliers -- people who would stand out for their productivity and ability to attract new people; and all-rounders -- people with a broad skill set who could quickly adapt and do many things, unlike specialists. Also, I made sure not to rush, and instead, I focused on bringing in the best people whose skill set would make a difference. It took me three to four months to hire the second engineer but being cautious paid off.

 

Developing our startup culture

We all carry layers of different cultures that we absorbed while working in different places, and it is tempting not to replicate those cultures. But we had our mission and vision, and I wanted to build a culture that would reflect those and make our day-to-day work more purposeful.

An important cultural aspect of most startups is ambiguity, which helped me sharpen my leadership reflexes. Sometimes decisions were to be made in a split of a second and, more importantly, in the midst of ambiguity and uncertainties. Many important decisions were on me to make; I could not expect the CEO to advise me on building the engineering organization or hiring for technical excellence. In fact, it was expected that I would make those decisions; after all, I was hired to do that. This contrasts with what an EM in large corporations is expected to be doing, where they have a set of specific tasks they should complete.

 

Also, the work pace would change a lot and without much anticipation. Some periods would be insanely hectic before one is back into calm waters waiting, for example, for another customer to sign up. While the first few customers could happen fast, it would take time to build a product and expand a customer base.

Lessons learned

• Before joining a startup, do thorough research. Know what to expect, learn about the startup’s mission and vision. Otherwise, you may find yourself amid chaos, wondering what you are doing there. But if mission and vision resonate with you and your career goals, you will take that chaos for a lifetime opportunity.
• Be an active participant in how company culture will be defined. Don’t leave it to just the executives and HR. Especially pay attention to culture during the hiring and don’t hesitate to scrutinize candidates on cultural issues. I don’t like the concept of culture fit, but I actively seek people who can be cultural contributors to help push it forward as the organisation grows.
• In a startup, you have to accomplish stellar results with limited resources. Whether you are constrained by a budget or a limited number of people, constraints will be there. Learn on the fly, and improvise. Be prepared that the learning curve will be steep but also very rewarding with so many opportunities along the way.
• It is much easier to associate your work with business outcomes in a startup. In large corporations, EMs will find it challenging to attach their work to larger business outcomes. What is great about startups is that you can see how your day-to-day work directly impacts the key objectives day in, day out.