Engineering, product and design skills are, after all, highly fungible. But for many people who attempt to make this transition, the gateway to entry can seem unreasonably hard to unlock, and the world on the other side more difficult to make sense of than anticipated. 

In this article, I’d like to share my perspective born out of my recent transition to Twitter after a decade in startup land. Since I've joined Twitter, I've spent many an hour ruminating on this topic, especially through the course of my onboarding and during conversations with candidates mulling career moves. Hopefully, my lived experience can shed some light on the opportunities and challenges facing interested readers.

Caveat emptor, a topic like this requires making generalizations. Neither startups or established tech companies are an objectively better option and every company is unique in its own way. The best way to approach the decision about which is best for you is to first identify your learning and skills development goals. What is it that you wish to accomplish in the next stage of your career? Depending on the answer to your question, any company could be perfect for you.

If you are considering making the jump from a startup to an established tech company, here are eight things you need to know:

Note: To establish a clear distinction in the coming narrative, consider the typical startup to be a growing tech company that is <4 years old with <200 employees, and the typical established tech company as one that is older and profitable with thousands of employees. 

1. The types of experts 

At startups, early employees are often generalists who have a breadth of understanding across problem domains and functions. In the early days, it's important for startups to be focused on one or two central concerns, and everybody has to have a first principles understanding of the business in order to make good decisions. At the same time, new functions have to be established from scratch, requiring these folks to rapidly understand the 101 of multiple domains. Until the company reaches a level of complexity that can't be kept up with, these employees typically stay involved in a range of decisions that can benefit from their wide context, giving you in turn a chance to interact with and learn from them. 

At established companies, you're likely to encounter many people who have spent several years diving deep into a relatively narrower group of problems. These folks are often the best in the world at what they do, and interacting with them will give you appreciation for the nuance and complexity behind seemingly small decisions. This is reflective of the fact that when you operate at a mature scale, incremental impact in focused areas can have huge effects. Personally, my most rewarding experiences in the last year have come from whirlwind deep dives with senior engineers at Twitter on the data, algorithm, and product challenges of ML recommendations.

2. What you will own 

Assuming your skills are equally valued in both setups, you’re likely to have a smaller piece of ownership in established organizations. However, the larger the company, the bigger the stage on which your work is projected and amplified. 

At smaller organizations, you're often entrusted with handling big pieces of the puzzle. This can give you a feeling of control and the freedom of ownership. It can also be dizzyingly empowering if your startup achieves escape velocity. It doesn’t necessarily, however, provide a greater magnitude of expected impact; I for one have built multiple projects during my startup days that now rest in the graveyard of obscurity due to lack of distribution. 

3. Leveling and titles 

Titles such as Senior, Director, and VP carry a lot of weight at established organizations, compared to startups where your title may be more elevated due to your size of ownership. That’s why it's not uncommon to hear startup employees complain of being ‘down-leveled’ at larger companies. The way to wrap your head around this is to benchmark yourself against the definition of your level in the career ladder of the company that you're considering, rather than working off of casual interpretations of titles (this applies to any career change since titles are not created equally even across bigger companies). The flip side of this coin is to not take your title too seriously when you’re at a startup, and calibrate more on the skills and responsibilities that are expected of you. 

4. Risk and burden of proof 

My experience with startups is that the risk of not acting is often greater than the risk of taking the wrong action. There's usually more value to be gained in the near-term than there is pre-existing value to protect. This is a microcosm of the fact that most startups derive their valuations from the lure of big bets paying off. 

With larger companies, you need to be more careful with applying the metaphorical pedal to the metal. You've typically got more users and revenue to watch out for that your actions could risk negatively affecting. In practice, this translates not to taking fewer risks, but requiring a higher burden of proof before taking leaps. 

5. Existing context 

At companies that have operated at scale for a while, the work that you do has to typically layer on to existing systems that have been around for a while. This means that to make a meaningful contribution, you need to understand both the work that’s in production and the decision-making process that resulted in things turning out this way. In my time at Twitter, I’ve found a new kind of hero: the uncanny operator who knows where to look for relevant information, which bits to double-click on, and how to organize information into mental models that can help them see why things are the way they are.

At startups, it’s easier to roll your sleeves up and hit the ball out of the park with your maverick swings. The existing canvas is usually much more sparse, which means you can get to painting in broad strokes without much ramp-up time. 

Over time, I've come to appreciate both flavors of work. There's a thrill to building rapidly with the feeling of exploring the wild west, but there is also a uniquely humbling and educative quality to having to take over a chess game several moves in and make deliberate progress. 

6. Tooling and levels of abstraction 

For software engineers, the tools of the trade are likely to vary depending on the type of company you choose. Larger companies often have internal tools, frameworks, and quirks tuned to the needs of the company, built to allow developers to focus on the problems that they’ve been hired to solve. Startups typically rely almost entirely on open-source software and public clouds. The former approach can be an enabler of development velocity, but only once you've navigated the company-specific learning curve. 

On the flip side, engineers at startups often have a greater impetus to think about multiple levels of concerns (e.g. startup product engineers often don’t have dedicated platform support and therefore develop a stronger intuition for costs) and to keep their eyes open for developments in the world outside their company's code base (since the answers aren’t likely to be available internally). 

7. Process 

Depending on your experiences, the word ‘process’ can bring up a range of emotions. Established companies usually have best practices and rules for all sorts of actions including hiring, promotions, privacy, exceptions, and more. This is a function of a need to maintain standards and deliver outcomes in a repeatable fashion. Startups often have a freer hand if their culture and norms haven't solidified, and since they can often rely on the decision-making skills of founders or senior employees as a substitute for process. 

Personally, while I do enjoy the freedom that startups offer, my time at an established company has made me swear by the need to codify best practices. For example, the meticulousness with which interviews are run to ensure objectivity and eliminate bias makes the startup hiring processes that I’ve been privy to seem almost renegade in comparison. 

8. Career mobility 

Most established companies give capable employees flexibility to experiment with role changes (e.g. IC to management), domain changes (moving across teams), and even geographical changes (doable when you have multiple offices or flexible work offerings). This is a consequence of having the scale to entertain such possibilities, and the latent demand from employees that the company find a way to keep their learning going across multiple phases of their careers. 

Startups on the other hand don't often have the slack to entertain career mobility in a non-opportunistic fashion; they're typically constantly fighting to limit bus factors and look to overall growth as the rising tide that can slingshot career development.

Reflections

All things considered, both experiences can make for very rewarding career choices. The onus lies on you to do your research, consider the factors involved, reflect on your career goals, and make the right decision for yourself.