The Difference a Team Makes

Most side projects and companies start with a couple of founders: hard working, committed, believing in a grand vision… Then comes the time to hire your first employees, which can be a daunting process. Who should you hire first? When is the right time? How exactly can you convince great people to join a company they’ve never heard of?

I’ve been in that spot in 3 startups now. Even though we’re now 60 at Paddle, it feels like yesterday when we were just two 18-year olds (and an inflatable T-Rex) in a small room just outside of London.

We’ve learnt a lot since then, through a lot of great and poor decisions and at times hard lessons about hiring. Here are a couple of these lessons and the practical exercises we did to help us figure things out at the time.

Who should you hire?

I think there are two types of hire: either you hire to delegate, or to own. Both require a fundamentally different person and it’s only too common to mess this up.

This difference is tightly linked to what you, as founder, are good at and love doing, which is why it’s really important to start figuring this out before you write a job ad.

I found an exercise we did with Kindred, one of our early investors just after Series A, particularly useful in that regard.

I noted down everything I had done in the last week, whether it was checking emails, calling someone or designing a new feature. I then categorised them and drew a pie chart showing how much time I spent.

I then drew a second pie chart with the time I’d like to actually spend 3 months later, based on what I thought I was good at and what I actually liked doing. For me, this was spending less time on general sales and marketing and having more time to engage with large or strategic customers, as well as thinking about how we could position a new product rather than diving into Google Analytics.

By diving into the difference between these 2 charts, I realised that I was spending a lot of time on our product as I wanted, but mostly on writing tickets and doing lower level product work. This is the reason why we started looking for a product manager.

When should you start hiring?

Whether it’s for your first hire when you’re just founders, or senior hires once you’ve grown, the right time to hire is when you realise that you’re not doing a good enough job at something you think is critically important (later you learn to anticipate the things you’re not going to be good at).

Once you’ve decided that now is the time and made that first hire, one of the biggest fears to overcome is no longer being involved with every aspect of every decision, whether it’s about your product or marketing. It’s actually quite hard as a founder to go from being the person who makes all the decisions.

It’s only natural to want to hire people who you think will make the same decision you would, seeing them as an extension of you. In practice the best hires tend to be the people who make better, more informed decisions than you would. This can, at first, be a difficult pill to swallow.

You’ll need to entrust these first hires and empower them to make decisions, even if sometimes you disagree with them. They will have a lot more data and focus on their topics, allowing them (most of the time) to be be more informed than you. Have an opinion, go against theirs if you think it really matters but otherwise just let them do it.

Being emotionally able to trust them is both something you need to work on, and a great way to decide if you’re ready to hire that candidate: lack of trust early on is a no-go. Later on you’ll use your company values to replace that early-in gut feeling, and keep hiring people you can trust.

How do you attract your first hires?

There are 3 main rules in my mind: have a clear definition of the role, spend time outreaching to people and have really sincere conversations with them.

Write a clear definition of the role

Go through that process, define what they’ll do vs. what you will do, what you really want from them. Check out other startups, especially those at a later stage in your field or city to see what great people look like. You will probably not hire people via traditional job ads early on but still go through the exercise of writing a job description/ad, as it’ll help both you and your first hire be clear on what it is you actually want.

Spend time on outreach

Let’s be clear: in the early days you’re unlikely to have a great person find out about you on their own, just as you’re unlikely to have customers find you on their own. Not only are you not well known or de-risked just yet, you’re also probably not doing well in the very thing it is you’re hiring for.

A tactic that’s worked well for us is going to events, meetups, asking people you admire at great startups for their time and speaking to them about how they would hire themselves and what it is that makes a great hire in their field. The best outcome is them deciding to join, the worse outcome is them recommending a couple of people they know.

Use your network a lot, and if you don’t have one yet make sure you build one. Your startup may be risky but you may not be: if a former colleague tells their friend that you were awesome, they’re not going to think about it as a crazy idea but as a crazy smart person.

Finally, you can use recruiters if you have the cash ;)

Be really sincere

Just as you need to trust your first hire, they need to trust you back: don’t lie to them or over-promise but rather spend time being really sincere about what it is you are building, why you wanted to build it in the first place, and why you want them to join you.

Explain the toughest problems you face in their field, ask them how they’d solve them and if they get excited about solving them with you, you may have a great first hire!

About the Author

Christian Owens is the founder and CEO of Paddle (LinkedIn, Twitter).

Prior to Paddle, Christian created his first software business from his bedroom at the age of 14. Having grown the business to over $1m in revenue he decided to quit school at 16 to focus on building startups, and founded Paddle when he turned 18.

In 2016, Christian was named one of Forbes’ “30 under 30” and as a Thiel Fellow by the Thiel Foundation, which supports those who learn by doing rather than by following conventional paths like college.

About Paddle

Paddle exists to help software companies succeed and are building the platform they use to run and grow their business. We take away all the complex and frustrating parts (from payments to licensing to analytics) and empower them to test ideas, increase sales and scale faster.

We’re still early in our journey to be the default platform for all software companies but we’re making good progress: we’re used by over 500 businesses, Deloitte Fast 50 named us the fastest growing software company in the UK (we’ve tripled revenue every year since our launch in 2012), and we’ve raised over $17m in funding from incredible investors such as Notion, BGF and Kindred.