Episode overview

Only a handful of people get to be a C-level executive. There are even fewer that are entrepreneurs that have successfully exited.

Andrew Davies has done both.

What are the skills Andrew has learned along the way that have made him successful? What does he think successful startups look at? And how does he look at hiring?

We’ll dive into Andrew’s story of entrepreneurship to CMO and how you can use it to level up your marketing career.

Episode highlights

• What Andrew's career looked like prior to joining Paddle as CMO


• What marketing skill Andrew thinks is important for both startup marketers and marketers at larger companies


• Why Andrew decided to move to Paddle even though he held a senior role at Optimizely (acquired the company he help founded)


• What culture traits do the best startups have


• How Andrew capitalized on building in public to help promote Paddle's acquisition of ProfitWell


• How to prepare your team as a leader if your company acquires another company


• Why you shouldn't just immediately leave a role when things aren't working out your way


• What traits Andrew looks for in people he hires


• What Andrew likes to uncover during interviews


• Where to go if you're looking to level up your marketing career


• Where Andrew thought his career would go when he was younger

Episode links:

• Follow Captivate Talent on LinkedIn, Twitter, Instagram, Facebook, YouTube, and TikTok


• Connect with Chris Gannon on LinkedIn


• Connect with Andrew Davies on LinkedIn

Key takeaways

[00:00:57 ] What Andrew's career looked like prior to joining Paddle as CMO

Andrew always had an interest in entrepreneurship. During college, he attempted multiple business ideas. One of them ended up being very successful with him and his co-founder eventually selling the company. After selling, Andrew joined Optimizely, the company that acquired his company, before eventually joining Paddle.

“I went to university with a scholarship from Deloitte. I was working with them pre-university in their consulting team technology.

I went to uni with one goal, which was to graduate with my own job so I didn't have to go back to them.

I started a couple of businesses that all failed terrifically at university and ended up with a business that turned into a SaaS business that I grew with my co-founder over the course of 10 years and we finally sold in 2019.

Then we joined an Insight Venture Partners roll up that we sold into which ended up buying Optimizely. We rebranded the whole thing. So I was running global corporate marketing there and alongside a whole bunch of advisory work on the side with SaaS businesses.”

[00:03:06 ] What marketing skill Andrew thinks is important for both startup marketers and marketers at larger companies

If you want to grow your marketing career, you need to be strong at internal marketing. Whether you work at a smaller business or a larger company you will have to collaborate with others. Being strong at internal marketing and getting others to buy into your ideas is key to career growth.

“If we talk about marketing, the marketing of your marketing becomes as important as the marketing work itself.

And some people hate that, but it's just a necessary part of a growing business that, you know, people who wanna just do the work, they often don't scale into those larger environments because talking to others and collaborating with others and preaching your gospel internally to others is as important as the work you're doing.

Because getting that resonance and echo and halo from everybody else is really important in a larger company.”

[00:05:13 ] Why Andrew decided to move to Paddle even though he held a senior role at Optimizely (acquired the company he help founded)

It’s important to look at culture, company trajectory, and business model when making a move. For Andrew, those things lined up better for him at Paddle. Andrew felt like he would also have more fun taking Paddle to IPO.

“I changed my mind because I just felt that I'd have more fun and more impact and running to IPO at Paddle instead. And there were really three things that did that for me. Number one was the people and the culture at battle.

Number two was the massive ambition of the business. And then number three, was the unit economics of the business that made me confident that we could go and achieve those ambitions.”

[00:06:45 ] What culture traits do the best startups have

The best startups stay hungry and stay humble. They need to be ambitious but they also need to be open to new ideas. Working with people that work like owners can help to provide valuable learning for your career.

“One of the things I recognized at Paddle was a real hunger to get better and a real hunger to push forwards. And that hunger and ambition was also paired with a humility to say, actually, we want new opinions. And so, you know, when you come into an organization and you've got lots of new ideas, it's very easy for people to be defensive about it, not being inventive there.

And it's something they've tried before. And I recognized as a team here, not just the leadership team, but throughout the rank, people were willing to kind of give stuff a go, even if they tried it before or listened to a new person coming in. So those, those are important.”

[00:09:51 ] How Andrew capitalized on building in public to help promote Paddle's acquisition of ProfitWell

Andrew has been a part of acquisitions a few times. Since he was pretty familiar with the process, he took the opportunity to document it to help others. They used one of Andrew’s friends to direct the film and have plans to release more content around it.

“We made a decision quite early on to kind of swing for the fences with this, not just in the size of the acquisition and the way we did it, but the kind of building public nature that we went about it. And so, you know, we recorded a documentary of the entire acquisition process.

And so, you know, I think one of the benefits of having seen a few of these processes was the willingness to kind of stand and say, come on, let's just, let's do something above and beyond just getting it done. Let's try and capture it for the benefit of the market as well. And so that was a fun process and it was great to be working with people who are up for that as an experiment as well.”

[00:13:41 ] How to prepare your team as a leader if your company acquires another company

Acquisitions are usually complex. Everything won’t run smoothly and there is going to be some chaos. The best way to prepare your team is by setting the right expectations. Make sure you’re hearing concerns and addressing them.

“Don't expect clarity. It's gonna be chaos. And the three tasks I've had for our marketing team are to please be vocal about your views and concerns. Number two, please be flexible, please be flexible and patient, as we work through this and number three, be positive, you know, add positivity into everything we're doing.

If you can do those three things we can walk through this journey of chaos together. And I think setting the right expectation is really important.”

[00:17:58 ] Why you shouldn't just immediately leave a role when things aren't working out your way

There are times when you should leave a role, but you shouldn’t just leave because it’s hard. Everyone goes through challenges. But if you’re able to stick through them and overcome them, that’s where you might see even more career growth.

“ I think often in a world that's fueled by lots of aspirational content on every social media platform and lots of chat around, you know, moving up in the world. I think it's also really important to recognize that if you are on a train, that's moving somewhere, just sticking with it and holding your nose to the grindstone and learning.

It could be a really good strategy and, you know, I'm a big fan of people who have that degree of stickability.

[00:19:56 ] What traits Andrew looks for in people he hires

Two big keys for hires are trust and willingness to receive feedback. Andrew says when he’s hiring, those are the first things he looks for. It’s okay to fail but being willing to learn and trust that there is a way out will help you grow.

“I love being in a high trust environment. I think the counterpoint to that is the ability to have hard conversations with each other and the ability to welcome that and not be defensive over that. So those are two things that are really important to me. So I love people who are willing to speak to me.”

[00:23:23 ] What Andrew likes to uncover during interviews

Andrew likes to look for consistent learners during the interview process. He asks people where they go to learn and how they learn. Most professions don’t stay the same so knowing where to