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This puts us in a pretty logical spot to matchmake candidates and startup jobs. It’s always interesting to hear what each side thinks they’re getting, and then in hindsight what they actually end up with.

Sometimes job-hunters lump ‘startups’ into one category and assume all startup experiences are the same, especially if they’ve never worked at one before.

In reality, startup experiences can be vastly different depending on stage, whether it sells to businesses or consumers, leadership etc. Which kind will you join? I jotted down some factors that you could consider in your decision-making.

In my view there are two parts to this process: (A) finding out about the company, and (B) finding out about yourself.‍

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A. The Company

Thinking about where you want to work has some overlap with where VCs want to invest:

1. Team - do you respect and have faith in the management team? Some founders are more impressive than others.

If the company is quite large already, can you imagine working well and learning from your direct manager or immediate team?

In Asia, I’ve noticed that people place a lot of emphasis on a founder’s educational background, but just because someone went to a brand name school doesn’t mean he or she is going to be a great manager to learn from. Personally I think founders who have built or led startups before inspire more confidence, some examples from our portfolio being Chang Wen (Ninja Van), Gabriel (Saleswhale), and Paul (Horangi).

2. Culture - Some companies are known to be aggressive, some are very community-driven, data-driven, buzzwords-driven etc … Can you feel at ease with the culture, and the environment that you’ll be spending at least 8 hours a day?

Don’t get bedazzled by the superficial stuff like swanky offices and amazing snacks. Great culture doesn’t mean a lot of ping pong. As one repeat entrepreneur says, “culture is about how the company makes decisions, what does the company prioritize, what types of people do well there, etc”.

3. Product and/or purpose - do you believe in the product that you’ll be building or selling? Does the purpose or modus operandi of the company resonate with you? Will you go the extra mile because you feel so strongly about solving problems for these users?

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B. You

Choosing a new job requires some serious self-reflection. Be honest with yourself on what you want, and what you can contribute to the company.

The major differentiating factor between most startup experiences is the stage you join. This is what I’ve observed on the different working environments at different stages:

Even though I put this in a tidy table**, in reality it’s in flux and it’s all relative.

As a founder CEO said to me, “it’s not about what kind of job you want, but what kind of life do you want? Because it can become so consuming.”

What do you really care about - impact, learning, financial reward, or work/life balance? It’s almost impossible to find a job that scores highly on all the above factors, so think about what you’re seeking and what you can compromise on.

Suggested resource for reflecting on what you want out of life: the Designing Your Life book.
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**A few caveats here:

• some variations depending on your seniority level, and how much of a superstar employee you are (e.g. your growth prospects are always going to be high if you’re a developer who can design and also do enterprise sales).
• the above doesn’t necessarily apply to startups who are bootstrapped and/or profitable, or US tech companies expanding here. E.g. Google’s expansion is going to be a very different experience to Stripe (although neither are actually startups now…).

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Mind the gap

Regardless of how well you’ve analysed the job opportunity and yourself, there’s bound to be some gap in expectations. If you’re lucky the job/company will turn out to be better than you expected. Anecdotally this seems to be rare.

Here are some suggestions you could do to get a more realistic view on your bright future ahead at the company.

Firstly - don’t believe the hype! I love this excerpt and pic from CBInsights’ newsletter:

“... this is a good reminder that if you're an employee of a startup that is good at hype and raising money but not actually building a real business, your common stock prob won't be worth much. You should think about looking for a new gig.

There are lots of startups that are building real companies.

Be careful out there.”

How to get a reality check? Look at the startup’s Glassdoor reviews (but take any extreme reviews with a pinch of salt). More importantly, talk to employees that work there.

Many people ask me what is the right amount of equity to ask for/receive. Check out AngelList’s jobs page to get an idea of what is market in this market.

If you are getting equity, make sure your handshake deal is formalised on paper somewhere, or ask to see your ESOP agreement if they have an existing one in use. Take a look at what Buffer, a startup famous for their internal transparency, wrote in a blog post explaining what ESOP means to their employees. If you’re not sure what the terms mean or whether you’re getting a fair deal, do some Googling or find an experienced start-up lawyer to review it.

I hope this has provided a more informed view on what your startup experience may be like; rather than scare you off.

Wishing everybody all the best :)

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Written by Lucy Luo, a former Investment Associate at Monk’s Hill Ventures

Many thanks to JS Ng, Michele Daoud, Hsu Ken Ooi and Jessica Kwok