The stuff you really should know when joining a startup.
The highs are high, and the lows are low: do you think you could work in a startup?
(Cue David Attenborough Narration):
“Look at the startup employee in their environment: a small, chaotic office with the scrambling of a mad person written on the walls, claiming to take over the world.
“Study them more closely; their dilated eyes, the worry lines of their forehead, the grey hairs. But wait, look at how they get really excited and start to celebrate the slightest increase in conversions as they walk through and get stuck in the messy middle”.
Rand Fishkin, in his book, Lost & Founder , suggests that a startup’s culture reflects the founder’s characteristics.
I’ve worked in a few startups and on reflection, he’s right. Some were chaotic, crazy, probably broke too many rules - all whilst the founders were navigating through whatever was thrown at them that day.
The thing is, if you are joining an early-stage startup there’s no clear way to get what it would be like working there as the culture hasn’t necessarily been created yet.
You’re part of that story.
I recently spoke at Shine Bootcamp on this very topic, looking at the lessons I’ve learned as an early-stage startup employee. I.e. someone who joins at the customer discovery / customer validation stage.
Why I think you really oughta know this stuff before joining a startup.
A lot of the content out there is for the founder and helping their growth, mindset and ability to work in this type of environment.
I think there’s very little info out there for the early employees, the ones that put their faith in a leader, and are involved in the origin story.
And yes, whilst some could argue that the risk /pressure may not be as great - I’d ask you to think about it as a different type of risk and pressure.
Do you think you could work (and thrive) in a startup?
You’ve got to:
Be comfortable with, and used to failure
Celebrate wins differently
Be mission-driven, not profit-driven
Open to, and engaged by the pursuit of learning new stuff.
Let’s say you’ve come from a business where you had a clear idea of what ‘success’ means.
This could be the sales targets being met that quarter, an increase in LTV, delivering product updates on time… whatever.
When you join a startup, the chances are it hasn’t quite realised what a successful milestone is.
Here’s what I mean with a few examples of what success looks like in early-stage startups:
Getting a ‘yes’ after 100 ‘no’s
A group of people* telling you that they’d pay for your service
Working with one other person for 90 days straight and you’re still talking to them
A lead generation campaign completely failing
A subscriber staying for that extra month.
*that aren’t your Mum, your Nan or your best friend.
These are successes because each one means you’re learning something new.
In other words, you need a growth mindset to really thrive in a startup, you need to see the micro-successes - the smaller steps to show what you’re doing is right.
“You need a growth mindset to really thrive in a startup, you need to see the micro-successes”
Reasons why a startup environment may not be right for you.
If you like your structure, maybe think again.
Startups involve ‘breaking things fast’. And whilst I am not really a fan of this saying, it gives you an indication of what it’s actually kinda like: you’re working against a depleting cash source in the bank. You’re not getting in sales whilst you are testing hypothesis or channels.
Job security? (Hahahaha).
Startups typically have around 3 months’ cash in the bank (it’s something to do with inflating valuations). This means you’ve always got this feeling at the back of your mind that you could have your hours cut. And, you need to keep an eye open for other jobs to pay the bills.
Dilution of your skill set.
If you think your role will be 100% marketing-led when you join, think again.
(Sorry, not sorry).
When I joined Careercake I thought I was going to only be involved in marketing. I didn’t realise that with such a small team at such an early stage in the business, that wasn’t the case.
I was involved in sales, pitches, presentations, admin, sorting out the customers, talking with the devs if the site went down.
You end up doing a lot of things that may be 1) outside your comfort zone and 2) outside of your interest zone. But it’s not until you validate the idea, start testing and setting up the channels when marketing truly comes into its play.
Startups feed into imposter syndrome.
Because of the dilution of your skill set, there are going to be days where you question whether you’re any good at your job.
Maybe you weren’t great in the sales pitch, perhaps your marketing is taking a lot longer to deliver results because you’ve not been given enough time to work on it ‘properly’. It can be a breeding ground for the feeling like you’re not very good.
Questions to ask when considering joining a startup:
These are a list of things/questions/insights I’ve picked up over the years:
What’s the current run rate?
Where do you see the industry headed? Who are you selling to?
This will give you an idea into what type of marketing you’re going to be involved with.
If your future founder is claiming they want to take on Amazon, yes, that’s inspirational BUT if they want to take on Amazon but aren’t prepared to assign a proper marketing budget… well, then…
What’s your plan for the business?
Do they have an exit strategy? Are they looking to build a sellable startup - i.e. you build the idea and then sell the concept to someone else with the resources to scale it.
What support does the CEO have?
Do they have access to and regularly engage in coaching/mentoring?
Do they have an idea what they want to achieve in the next 3-6 months?
What does successful marketing look like in their eyes?
What do they envisage the type of marketing you’ll get involved in?
What’s the background of the core team?
(List the CEO, the investors, key partners’ backgrounds. Are they sales? Engineering? CTOs? Learn the landscape to see what you’re entering / who’ll be an ally.
These are just a few things I think it is worth considering when joining a startup. Let me know if I am missing anything by contacting me! (Plus, it’d be nice to see if anyone’s reading this far down…)

