So, you wanna work at a startup?
[Hopefully Helpful] notes for software engineers looking to join startups
I’ve spent about ~10 years of a ~14 year long career in startups. At times, people ask me if it’s the right time in their career to join a startup. Or what’s the right size of the startup to join. Or which startup to join.
As someone who has recently rejoined the world of startups, I was conflicted with similar questions.
So, here’s an attempt at ill-formed career advice. A startup-career-LifeStage ready reckoner, if you will.
- Most important question - What’s in it for you?
- Not so important question - “Can I make it”?
- Final Words
- Footnotes
Most important question - What’s in it for you?
Any job is a business transaction. Your best friend may be the founder or founding engineer and may rave about the place and it’s prospects (“It’s gonna be the next Google”).
That brings FOMO. Who wouldn’t want to join the next Google. But understand that FOMO is not a career strategy. Nor does anyone have a magical, guaranteed path to success & riches.
Instead, it’s helpful to remember that at different points in your career, a startup will have different learnings to offer to you.It’s important to weigh the tradeoffs and understand how this fits in your career trajectory.
Go in for these learnings; and if you make millions along the way - that’s just the cherry on top.
As with any big decision - there are multiple facets to this. I’ll try to narrow it to 2 high level facets - what you’ll be getting into (based on the startup stage) - State of Affairs & Callouts & what you stand to gain from it (based on where you are in your career) - Potential Gains
Seed Stage (Founding Engineer / 5+ Engineers)
State of Affairs
- PMF is everything. This involves significant iterations, especially if your founders know what they’re doing (more, if they don’t).
- Code is just an enabler. Abstractions, code quality, finesse - nothing matters.
Callouts
- You must be passionate about what the startup is building. This serves as fuel in those charged up & taxing moments. Read it again, in bold: DO NOT JOIN A SEED STAGE STARTUP IF YOU DON’T BELIEVE IN THE PRODUCT
- Trust in the founder(s) is mandatory. Awe is optional.
- Your ESOP grant should be measurable in percentage points
Potential Gains
0-1 Years of Experience
A ride of a lifetime - if you stick around long enough & the startup succeeds.
Startups are addictive and if you start your career at one, other larger companies just won’t cut it for you.
So, if you’re forced to move to BigTech - you’d probably get bored.
2-4 Years of Experience
Agency & Decision making - something you don’t get at bigger companies.
Stick around long enough to watch your decisions bring impact and/or failure.
5-8 Years of Experience
Impact. Your decisions & pace of execution has direct impact on the customer.
If you’re good, then you’ll rise through the ranks as the startup grows.
8-12 Years of Experience
You should think long & hard why you are not doing your own startup.
Perhaps, the only reason to join would be if you really believe in the mission & would have done something similar anyway.
13+ Years of Experience
Front row seat on how to build a startup without being a founder.
Highly recommended if you intend to build a startup yourself & haven’t yet worked at an early stage startup
Also, You should think long & hard why you are not doing your own startup.
Perhaps, the only reason to join would be if you really believe in the mission & would have done something similar anyway.
Series A (8-30 Engineers)
State of Affairs
- They think they have PMF
- Lots of [exciting / challenging / life changing ] fires to fight
- Mostly, there will be a shared file / google doc with passwords in it. Try to get access to this file. That’s the way you know you’re in the elite group
Callouts
- You’ll get to see all the coding standards that the books, software engineering professors or your mentors at BigTech warned you about.
- Success at a Series A startup usually stems from the impact you can bring, which stems from how much you think about the product, which stems from how much you love it. So, it’ll really help if you believe in the mission of your company.
Potential Gains
0-1 Years of Experience
A fast paced career path if you’re good. Also, a healthy coffee addiction.
But, reconsider either Series C or Seed stage startups based on your risk appetite.
2-4 Years of Experience
Engineering challenges that stem from a crunch of time, resources & everything else.
If you’re good, you’ll be leading teams soon.
You’ll need to get things done quick, and hopefully in a way that doesn’t need you staying up as oncall all night. Fun.
4-8 Years of Experience
Ability to handle stress. I say this with a positive connotation.
Mostly, you’d be leading very high impact initiatives & directly responsible for success / failure.
You’ll be unsure of yourself at every step of the way. Fun.
But once you learn to handle this kind of stress, life in general will be easy.
8-12 Years of Experience
Getting in early at series A means you’ll be a known face as the company grows - which promises to be a very lucrative career path with lots of titles on the way.
As a startup matures to Series B / C / D, you’d be responsible for charters worth millions of dollars and the agency to take decisions (VPs at bigTech will envy you).
It’ll be like running your own startup within a startup. Very Nice.
13+ Years of Experience
VPs & SVPs at BigTech will envy you.
Your contributions will ideally impact the success trajectory of the company.
But with great power comes great responsibility. Don’t join if you don’t believe in the product or you’ll ruin the careers of a lot of people. Don’t be an asshole. Or worse, a greedy asshole just in it for the ESOPs.
Series B (45+ Engineers)
State of Affairs
- They may think they have a path to IPO (“12-24 months!”)
- “Scaling issues”. Be it people, tech, processes - perhaps all of them (especially if the startup is doing well)
- OG engineers who are extremely passionate about the startup; some of them will be great; some of them think they’re second only to Linus and Jeff Dean 1.
Callouts
- You’ll be challenged at all fronts - dealing with people, bad code, bugs, timelines, real & fake scaling challenges. If you are with the right people, or at the right designation - there’s a lot to learn and lot of gratification through impact
- It may be tempting for someone to zero-in on a Series B startup as the “sweet stage” to join the company. But be warned - the job requires you to clean up other people’s mess while meeting the demands of a growing startup.
- Don’t bother joining if there’s still a doc with passwords around. This company won’t IPO for the next 5 years (True story).
Potential Gains
0-1 Years of Experience
This is extremely tricky.
Paired with the right mentor & team, you’ll get to learn exactly how to build technology that works and doesn’t keep you up at night. And fast.
Paired with the wrong mentor & team, it’ll be an absolute nightmare.
Join only if you know someone or if you know someone who can vouch for someone.
Another good litmus test is if this company is ready to pay you around 90-percentile of the job market. They want to bring in good people which means they’ve brought in good people before.
2-4 Years of Experience
If you think you’re good, then this is a good opportunity for you to get in and start leading teams.
There will be just the right amount of agency & responsibility - which results in an ability to make decisions & have impact while getting to learn how to mentor people in a relatively “safe” environment.
Your mistakes won’t result in the company shutting down (hopefully). So you’ll get to make some and learn from them.
Don’t be too hard on yourself; but don’t start getting cocky either. You may become a “Team Lead”, but you have a long way to go.
4-8 Years of Experience
If you’ve only worked in BigTech, then this isn’t the ideal stage startup to jump into.
You’ll get f***ed from both ends. On one hand, there’ll be your “leadership” who’ll always expect you to execute fast. On the other, you’d have your juniors who’ll look down upon you for being too “process oriented” (or some other similar flaw due to your BigTech upbringing).
Basically, even if you have some good ideas - you’ll find you’re always having to prove yourself first. This will have nothing to do with you - neither of these groups know better.
If you’re switching from another startup, then it should probably be only if you feel this company has a better “brand value”, significantly higher potential than your current startup and/or a problem space that appeals more to you. Don’t leave a fintech for a fintech. [ Also, don’t work for a FinTech anyway. ]2
8-12 Years of Experience
Basically you’re being brought in to bring some order to the chaos.
Most likely, you’d be put in charge of a system that is running on it’s last fumes. You’ll have to clean up the mess while being counted on to take big bets & make large changes. All this while mentoring a large set of people. It’s a really fun place to be and can be very rewarding.
Word of caution: Never underestimate the current system. It’s also made by really smart people. It may look like it’s running on bandaids - but it does run. Understand that it’s this way because it was built in a hurry. Don’t be a snob.
13+ Years of Experience
Everything mentioned for the (8-12) YoE applies here too. Only better - since you can look to get a great title & a lot of equity.
Ideally, hierarchy-wise, you should be at most 1-2 hops away from the founders. It doesn’t sound right if you’re not. And yes, hierarchy matters in a high-growth startup (even though everyone thinks otherwise).
This will also help you get a front row seat to how the startup scales.
Word of advice: Mostly, you’ll be interviewed by & reporting to people younger than you. Be humble - and don’t join if you secretly look down on them.
Series C (125+ Engineers)
State of Affairs
- If the startup is growing & managed well - everyone feels empowered. People will be making millions of dollars worth of decisions in meetings & getting it done in weeks.
- If badly managed - lots of communication overhead, indecisiveness and frustrated engineers groaning about “the good old days”.
Callouts
- If it’s a well run startup, this is the sweet spot between being empowered to make a huge impact and having the resources to do so.
- If you’re relatively senior, your “distance from the founder” is important.
Potential gains
0-1 Years of Experience
The good & bad is similar to joining a Series B startup (so read that first). The same litmus test applies here too.
The good thing is, it’s not as tricky.
In the worst case, if you’re paired with a bad mentor / team, you’ll generally be able to change to a different team & problem statement after proving yourself for some time. So it’s not a death sentence.
2-4 Years of Experience
If you’ve only worked in BigTech, then ideally, the only reason you’d be considering joining this place is because you feel too suffocated at BigTech and want to unleash yourself & learn many things - fast.
I’d recommend joining only if you know the team & the manager / mentor you’ll be working with - preferably someone you’ve worked with before.
If not, then it’s a little dicey. What you “get in return” with this move would be quite nuanced.
4-8 Years of Experience
This will be a good place to grow. Most likely, you’ll be a team lead and handling more than one problem statement - which are growing in scale & complexity.
It’s a great opportunity to clean up the mess that exists from the past, while thinking actively about the future.
All the “best practices” you’ve heard / learnt about can be put to practice - and you’ll be relied upon to do so.
If you’re good, you can expect to have outsized growth.
Word of Caution: If you’re good, you’ll always be given more responsibility. There’s a tendency to burn out here. Embrace the hard work, but find ways to be more productive & efficient in your work. I know everyone likes feeling important, but actively find ways to make yourself redundant.
Also, leave quickly if you are not getting recognised & compensated for your hard work.
8-12 Years of Experience
If you’re good, then this would be a great place to grow. You should think actively about what you’d be bringing to the table and try to find a problem statement accordingly.
If you carry certain expertise (say, Search / Data Pipelines / Analytic platforms) - then you should leverage this to make some quick impact.
Be careful though - don’t pretend to know more than you do. You’ll be found out very very soon. If you can’t handle a problem statement, don’t be too proud to ask questions and seek advice from people who’ve been around for a while. Context counts for a lot here.
13+ Years of Experience
Everything mentioned for the (8-12) YoE applies here too. Only better - since you can look to get a great title & a lot of equity.
The only problem is, you’d probably be one among many people with the same title. (One of 5 Heads of Engineerings or Principal Engineers). This is not a problem on it’s own, except that you should expect some turf wars as the startup grows.
If it’s growing really fast - that’s fine (there’ll always be enough meat for everyone). If it is only low-double-digit growth a year , that’s when things will get tricky.
Series D +
I think the only reason to join a Series D+ startup would be if you see a path to IPO and a possibility of an outsized cash pay out. This usually holds true only for higher levels & designations. Also, the potential size of the IPO will make a huge difference to your expected pay out (Will it be 1B? 5B? 100B?). This can be a much easier decision as the “return” you’re expecting is money - and it should be easy to weigh the risk vs reward when it comes to other options on the table (including your current gig).
Keep in mind that Series D+ startups have the problems of smaller companies as well as BigTech. So really, don’t join a Series D startup just because you’re looking for “startup experience”.
Not so important question - “Can I make it”?
Invariably, this is the reason I’ve heard that keeps most people from jumping into startups. There’s this fear that after a while you’ll find it too hard or that you’ll lose out on work/life balance. Both of these may be true; but both may be false too. You’ll never know till you try.
I’ve managed to follow a mostly 8am-4:30pm schedule at a fast paced startup (went from 40M to 3B in 2 years). There are also others I know who work exclusively for startups and have thriving personal lives & hobbies. Besides, we live in an AI-first world where developer productivity can be super-charged if you have a solid AI toolkit.
Really, it’s all upto how you manage to hold on - and always keep the more important questions in mind: What are you gaining in exchange for the things you’re giving up Join a startup; keep asking this question every 6-12 months; and quit if it looks like you’re getting the short straw.
Hopefully, you’ll have a rewarding career spanning decades. Embrace the adventure for 1-2 years. My guess is that it’ll be worth it.
Final Words
Startups, usually, are all about being contrarian and right. So choose to ignore this framework and build your own framework to find success. If anything, I’d be the happiest if I could seed the thought of thinking in frameworks when making career choices.
PS: Liked reading? Hated it? Any thoughts/questions/comments? Please do mail me at [email protected]