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Paddle turns 10: Learnings from the last decade

This month marks 10 years since Harrison Rose and I founded Paddle. 

Since then, a lot has changed. We’ve grown to a team of 350 Paddlers (in 17 different countries), we’ve raised $293m in funding, we help over 3000 software and SaaS businesses run and grow more efficiently – and we made our tenth year particularly exciting with our acquisition of ProfitWell.

We’ve achieved a lot but it hasn’t all been plain sailing, there’s been challenges to overcome, problems to solve, and lessons to learn along the way. Here are some reflections:

It doesn’t get easier, the problems just change

When you’re starting out, the tendency is to think that the grass is always greener. That everyone else is finding it easier or doing it better. In the early days at Paddle, it felt like we were always one thing away from everything becoming a lot easier. 

As we continue to scale, I’ve learned that that isn’t the case. It doesn’t get easier, the problems just change.

You get through that funding round, then you have to deliver on your plans. You close that big deal, then you have to get them live. You make key hires and have to adjust processes for a bigger team and changing dynamics. 

Then, as you grow, how you tackle problems and any changes you make suddenly impact a much bigger group of people. Whether employees, investors, or customers. 

It’s constant and it takes a lot of persistence to keep going.

The importance of building a great team

One thing that makes it easier is surrounding yourself with a great team.

Building that team though isn’t easy. You need the right people, at the right time as your business scales. Finding strong leaders is particularly challenging. You need people who share the vision, who want to create something big, and come on the journey with you. We’ve brought some fantastic leaders into the fold over the last few years, without whom our business wouldn’t be where it is today. 

Seeing the Paddle team grow is something that, as a Founder, I really relish. Any time we have managed to get the full team together at our Summits has always proved a real highlight. It’s a chance to see the passionate group of people we have, and you learn about how people have grown in their role, or in some cases, how they have completely changed their career path. 

When you build a great team of people you trust, you can (and should) foster a culture based on feedback. Listen to them, and hear them when they tell you that you’re wrong about something – it helps the whole business to constantly improve and try new things.

Stay true to your mission

I started Paddle to solve the challenges that I had experienced when I ran a SaaS business as a teenager. Just over a year in, I realized that I was spending all of my time on stuff that wasn’t developing the product. I was managing payments, building subscription logic, and trying to navigate my sales tax liabilities. 

Paddle exists to stop anyone else from having to experience that. We take care of payments, subscriptions, and sales tax for software and SaaS businesses to help them run and grow automatically. 

That’s what we set out to do, and it’s what we still do today. It’s been a guiding principle in everything we do, and it hasn’t steered us wrong. 

As you grow, it’s easy to get distracted. There will be something shiny and new that you could build or the market will change and you’ll think about moving with it. When those opportunities arise, your mission should guide the decision making process – focus on the things that will get you there.

Grow with your customers in mind

Our mission also keeps us focused on our customers - and how we can make their life even a little bit easier. I love hearing from them, and seeing the businesses that sell through us grow.  

Particularly over the last few years, seeing our customers continue to grow through tough times has been humbling. At a conference recently, I spoke to someone who had used Paddle to successfully pivot their business when industries shut down through COVID – knowing that we helped in even a small way is a real sense of achievement. 

We’ve got a lot more to do and there’s a lot more to learn but I’m excited for the future and how we can continue to grow so that there are thousands more businesses who attribute some miniscule part of what they've been able to build to the work that we do.

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