Here's the thing: What no one tells you about joining an early-stage company
What you should know if you're thinking of diving into start-up life.
There wasn’t a manual waiting for me. When I emailed James to officially accept his offer to come aboard Tyk, I did so with no real idea of what I was signing up for.
That wasn’t to say I was entirely naive. I wasn’t coming straight into start-up from my corporate life, but via a brief sojourn into agency life, which had given me a crash course in commercial acumen and taken me to Singapore, where I now lived. I also grew up around small businesses like my family’s various ventures: two pet shops, a signage company and multiple software businesses between them. I knew the blood, sweat, tears and sacrifice they entailed, and I felt I was ready to be part of one.
I was, and I wasn’t, at the same time.
The last seven years at Tyk have been a rollercoaster. We’ve built a multi-million-dollar business from first principles, riding waves and tripping over ourselves and our mistakes along the way. It’s been the greatest education of my life, and on many levels I feel like there is still so much to learn.
Together with Tyk’s 150+ strong team we’ve created:
A company where people are genuinely excited to work with, or for, us
A remote-first pioneer (since 2016), proving you can build a productive, passionate, and high-performing culture outside of the traditional office
A quirky, challenger brand, standing out in a sea full of beige behemoths, only to last year be crowned technology Leader alongside them
Do I believe that anyone can do this? Honestly, no, I don’t. It takes drive, determination, and sheer bloody-mindedness persistence, at the very least, to get there, and with limitless energy needed to power it all. Even then there can be umpteen reasons you can stumble or fail - many out of your control.
But I do believe more people can do it than think they can - especially women and others from underrepresented communities, who I believe know all-too-well that feeling of fire in their belly and the hunger to learn, grow and, well, prove others wrong (just me?) The start-up ecosystem is still dominated by too many mediocre white men with family wealth and public school levels of confidence behind them, and it benefits all of us to change that.
So starting from today I want to share what you need to know about start-ups if you’re thinking about joining one. Or even just dreaming about maybe, one day, someday taking the leap. Some of these lessons might be familiar to you, a few may surprise you, and others may sound as attractive as being forced to watch Elon Musk take on Mark Zuckerberg in a cage fight. We’ll cover the whole gamut!
Got your swimming costume? Let’s dive in to our first edition.
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When you join a start-up, you’ll be working for a company you haven’t even met yet
What I want to focus on today is what I think is one of the most important, but overlooked, insights you should keep in mind when joining an early-stage venture. That is that you’re never really just joining ‘one company’, but several different ones, most of which you haven’t met yet.
That’s because at a successful start-up the business will be changing on a fundamental level with every milestone you reach, whether that’s a revenue milestone, a funding milestone or an employee size milestone (they’re all interlinked).
The name on your payslip may stay the same but behind the scenes you’ll be seeing a vast difference in your objectives, reporting, and resources (tooling and people) as you hit each one. Your targets will also constantly move (in one direction: up), with your business, sales and marketing strategy regularly adapting to help you hit them.
I’ve worked at Tyk for almost seven years now, but it’s often felt like I’ve worked at three or four different businesses in that time. In truth those new challenges have been a huge part of what’s kept me here for so long, but nevertheless the speed of change is confronting, and not anything I ever experienced at Savills or RBS.
And that’s not to say there’s never any change in those big corporates: you’ll also have good years and not-so-good. There may also be memorable events punctuating your time there: new leadership, takeovers, or profit warnings, all of which can shift the mood and priorities of the business internally. I myself saw two restructures in one long year at RBS, along with Stephen Hester’s shock exit.
But when you’re at a company with tens, or even hundreds of thousands of employees, you are essentially going to be a cruise liner for the large part of your journey. The seas might become rougher, you might grow or lose some people along the way, the strategies may change, but you’re still going to be the largest vessel on the horizon. And large things generally take a long, long time to move.
Contrast that with a growing start up, where every few years you’re going to need to build an entirely different boat, each with different skill sets onboard to help you sail it. Big waves also impact smaller boats much more dramatically: you’ll be building a bigger or stronger boat in preparation, even as you master sailing the current one. The positive is that you’re able to easily navigate change as you’re a smaller and tighter operation, with a lot more agility.
Charting Tyk’s journey: What this looked like in practice
I joined Tyk when it was practically a rowing boat of 17 people. We were bootstrapping, with good enough product-market fit to mean we were already covering our costs and didn’t need to take funding immediately (a very nice, and unusual place to be in the modern software space!)
Growth was happening, but slowly, as it depended on us reinvesting our profits into our people, product, and sales and marketing costs. Back then we didn’t have our own functioning CMS and our CRM was a glorified spreadsheet. We published maybe one blog post every month to our tiny, but super-engaged mailing list. After three years of slow and steady, positive growth, we decided to take external Venture Capital funding in 2019 to accelerate our trajectory through marketing and a push into the US market.
When we did reach our Series A in 2019, our priorities immediately shifted. You go from being answerable to your teams and your customers to being answerable to investors who are looking for results, and a sign that they will get a good return. The playing field shifts so the way you play the game has to too: your team structure, your reporting requirements, even your sense of humour on external blog posts!
And if that upped the ante, well just wait until you go through the rigmarole again, this time for Series B. At this stage you’re generally talking - and taking - much more money, with investors who are expecting a much more mature and future-proofed company to go with it. The level of scrutiny is noticeably (and understandably) higher.
In many ways every year at Tyk has felt like a foundational year, even as we’ve made huge progress from one to the next.
Our Series B happened in September 2021, when the world was still reeling from Covid, and at a time where I still had thirteen direct reports located from Atlanta, Georgia all the way to Singapore. It took a hefty six months, and all that time we were pitching to investors, whittling down options, and eventually doing extensive due diligence with the ones we moved forward with… oh, and our day jobs! It was one of the best experiences I’ve ever had, but it was a period of intense work (aided, at least, by the pandemic which meant I couldn’t have much of a social life anyway).
All of the above happened in just four years, and in the three years since we took that funding we’ve grown even bigger and matured further as a business. Our targets have also risen accordingly! From a marketing perspective we’ve refreshed our visual brand, done two rounds of positioning, and introduced an entire Revenue Operations function for better data-driven decision-making.
I found this table (above) showing the ‘year by year' journey so far from when I did our Series B investor due diligence. It’s very surface level - I mostly wrote it just to remember what we did, to be honest! - but it shows how much we were learning from first principles. I would tackle things quite differently if I were going at it again today, knowing what I know now, but it’s been quite the education.
And just reflecting on those mammoth changes we’ve made in seven years shows why the five-year plan is dead, and the two-year plan too. It also goes some way to explaining why I’ve felt like every year at Tyk has been a ‘foundational year’, even as we’ve made huge progress from one to the next.
In start-ups the only certainty is constant change
What has stood out to me compared to my corporate days is that, in a big business, you don’t feel that sense of new ground being forged very often - not unless perhaps you’re working on a specific innovation initiative or completely new product line. I would now find that very stifling or stagnating, but for others it’s an attractive prospect: you know what you’re getting, on the whole, day-after day.
If you’re thinking about joining a start-up, I urge you to be aware of this truth about start-ups. Be really brutally honest with yourself about how much you are able and willing to embrace change, how you can do your best to make that clear to Leadership, and be ready to get ahead of any changes coming down the line.
Unfortunately as companies grow, it’s a sad reality that the team that got you to one milestone may not all have the skills or inclination to join you for the next stage. Some team members may not even be aware that it’s a consideration even as you discuss it with them, so they don’t signal that they’re ready to face change, or willing to bend their role to make the necessary space for it.
This happens at every level of the company by the way. There are plenty of CEOs who have been asked to leave on hitting a new stage, when the investors weren’t certain they could lead the company through to the next level. You can look at my role too: I led the Marketing team through to 2021 and our Series B, only for us to hire a CMO after, who I now report to. Many would see that as a snub, but I didn’t, I saw it as an opportunity to prepare for, and then maximise. I don’t doubt that many others in my position would have left out of spite, or frankly have been asked to leave if they couldn’t get on board with the idea.
Trust in the Founders and their Leadership Team is critical
If the only certainty in start-up life is constant change, then you also need to be able to trust the people who will be navigating the seas with you. Your Captains, to really labour the analogy! This is generally the Founders, and, depending on the company size, the other senior leaders in the company (whether a Board, or Leadership Team, or both).
If you’re in talks with someone about joining their start-up, especially if it’s pre-seed funding or pre-Series A, you must do your own due diligence. Do not be afraid about asking questions: they should welcome this not least because it shows your interest in the company. If they don’t welcome it, it’s a red flag.
At the same time, when you ask questions don’t expect the Founders to have all the answers. They don’t need to, but you should ask them anyway in order to get an idea of the stage they’re at and how honest they’re willing to be about it. Often it’s actually fine if someone says ‘we don’t know’, but you need to know that they don’t know, so you can sum up the stage they’re at, what they really need from your expertise, and make a decision accordingly!
Often in early-stage companies, there isn’t much concrete data as you’re dealing with such small numbers, so you need to listen to your gut. Do you trust what the Founders are telling you? Do you think they trust you, and are willing to listen and respect your opinion? This is just as crucial as you being able to trust them: to really make an impact in a start-up, you need to be given the autonomy to run with ideas, to test, tweak and learn.
And if you decide to move, watch who they hire and who they keep over time. If you’re in a start up of twenty people, every person working there equals 5% of the culture. Is the culture these people are building one that makes you proud, and one that pushes you forward and helps you attract new people? Do the Founders recognise that, and strive to keep that?
And, even more importantly, do they move quickly to let go of anyone who doesn’t act in line with the values and mission of the company? The impact of even one person acting in bad faith in a small company cannot be understated: you need to have faith your Founders and Leadership Team have the confidence to make the hard decisions where necessary.
The company is going to change, but so will you
If you’d told me joining Tyk in 2017 that one day I’d be fielding terrifying investor calls, or determining how we were going to build a double-digit pipeline, I might have run in the opposite direction.
But just as it’s true that when you join a start-up you’re joining many companies you haven’t met yet, it’s also true that, as part of that journey, you’ll meet new versions of yourself along the way to meet the challenge.
As this well-known graph shows, progress is not usually a sharp line from A - Z but a series of peaks, troughs, and plateaus, slowly but surely moving up and to the right. And as you meet discomfort, and work through it, you’ll slowly see your comfort zone expanding: sometimes it’s so subtle you don’t even realise yourself (something I’ve written about previously).
What’s important is that you focus on two things: 1) the here and now, and 2) the ‘there’ you’re aiming for in the middle-distance.
Know the business priorities, work hard, ask for help, and one day you may look around you and see a version of yourself you once never imagined. And working at a company that’s unrecognisable to where you started seven years ago, which you helped build.
💌 Did this first edition of ‘Here’s the thing’ surprise you, scare you, make you roll your eyes at just how much you already knew this information? Let me know in the comments, along with any other topic you’d like me to cover in future editions.
❤️ If you nodded, smiled, shuddered, or felt a deep sense of YES I’VE BEEN THERE BEFORE, please hit the heart to show me you got the feels, and help me share this with others in the Substack community.
✨ And finally, sharing is caring. Did you survive start-up life with someone, or know a friend thinking about making the move? Do me a favour and pass this link onto them. Thank you!
Top post with great insights for one's career indeed.. and that CMO could not be more thankful to have a co-pilot like you Emma, complementarity, expertise, drive, curiosity, OKRs focus, adaptability, aptitude and attitude is what every team lead asks & expects from each of their crew, whatever the seniority. You built such a strong team and help shape our growth every single day through your passion for Tyk too, so THANK YOU.