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LATEST POSTS 📚

If you’re new, not yet a subscriber, or just plain missed it, here are some of our recent editions.

🐺 Starkian Leadership: The King Who Knelt. The last King in the North. And the greatest leadership story ever told.
🌱 Collection: What Is Your North Star Metric? A collection of thoughts from a collection of leaders.
💣 Neumannomics: A Deep Dive. Co-Founder & Ex-CEO at WeWork. How to build a cult, burn it the ground and buy it back again. 

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HOUSEKEEPING 📨

Been shook lately with all the political news coming out of the U.S. I worried about what’s going from two angles. Firstly, I think democracy is eroding and I think the world is heading down a more volatile path. The second is something that I am personally worried about. The worry I will end up too deep into an echo chamber that I can never make it out of.

I know that both of these books will have me digging my heels in against Trump. But I also want to make sure I am taking in opinions from the other side. I see so many good friends, that I genuinely think have lost their mind, either being too far left, or too far right. It’s one of the things that upsets me most about the world today. There is no shared truth—or seemingly less than ever before—that we can call agree on.

Most of the media that I consume is liberal media; Prof G, Vox, NPR podcasts. But I do read some techno-optimists blogs, and do watch All-In, some Pirate Wires (I despise the host) and enjoy a smattering of Andreessen, Elon, Thiel of course when they are floating through my podcast or YouTube feeds.

I don’t have a lot more to add. I guess I’m just sharing my fear of losing my ability to discern truth from fiction, or at least process information with minimal biases.

Anywho, onto today’s post. I think you are going to love it. Andrew and Paddle think and act a lot like we do at my startup, Athyna. They are also building out their own category, and winning. Hope you enjoy the read!

LEADER DEEP DIVE 🕵🏻

Andrew Davies, CMO @ Paddle

Andrew Davies is the Chief Marketing Officer at Paddle, the platform managing payments for 5,000 self-serve software companies. With $295M raised and the acquisition of ProfitWell under its belt, Paddle is just getting started in reshaping how digital products are sold globally.

Before Paddle, Andrew led corporate marketing at Optimizely, integrating five acquisitions and driving major growth. Even before that, he co-founded Idio, scaling it into a market leader in B2B personalization before a successful exit.

Beyond work, he advises and invests in early-stage startups, sits on the board of Ninety, and has a deep love for startups, problem-solvers, and underdogs.

Tell us about the problem you are trying to solve? Why this?

I was a software founder myself, so I've experienced this problem firsthand. We believe that software is born global. It doesn't matter where you are in the world; you can build a software company. I'm in Devon, you're in Buenos Aires, and we can both sell to the whole world, competing with everyone globally. This is partly because the world is now flat, with consumers everywhere able to buy your products. Many of the best companies scale through ‘product-led growth.’ We don't need to hire a sales team; we can just put a checkout on our website and start selling the digital product we've built.

There's a whole bunch of back-office problems that really stop founders from building the company they want because they're too busy dealing with that stuff instead of focusing on their product and their customers. Paddle takes care of all this complexity, helping you operate and grow your company globally so you can focus on growth.

And here is our opportunity: if more knew about the ‘merchant-of-record’ model, then their lives would be much easier and their growth would be faster. We like to say; ‘The world needs MoR!’

What did the zero to one for Paddle look like?

Christian Owens, the founder of Paddle, was incredibly young when he started—still in school. He built a software business but quickly realized that selling it was the hardest part. That led him to focus on solving the problem, not just for himself but for other companies as well.

Along the way, he discovered the merchant-of-record model, which allowed him to resell software and handle global sales complexities on behalf of businesses. That’s where the idea for Paddle was born.

Christian was also a Peter Thiel Fellow, incredibly sharp, and left school early to pursue his work. He started coding around 15, launched his first company shortly after, and by the time Paddle was founded, he was just 17 or 18.

What is your main day to day job as CMO?

I split my time across a few key areas. About 25% of my time goes into running the marketing team—building awareness, driving pipeline, and making sure our strategy is aligned. Then there's my role on the executive team, where about 25% of my time is spent with the other leaders driving key projects forward and managing our business.

The largest chunk of my time—around 50%—is spent engaging with the market. That means talking to customers and prospects, hosting events and dinners, speaking at industry conferences, and staying plugged into what’s happening in our space. It’s about understanding where the market is headed and building relationships with people who are, or could become, Paddle customers.

What does your team look like? Who are your direct reports?

Paula, leads our Demand Generation team. She handles things like emails, ads, and our webinars. And Tharshan - he works by himself without a team. He tries out new ideas for us. And these are pretty much the key people who help me manage everything we do in marketing.

Explain your philosophy around leadership? How do you think about it?

When it comes to the marketing function, I believe my job is to teach the team the rules of the game so they can go and play it themselves. I'm not smart enough to be a top-down, directive know-it-all. Instead, I aim to understand the market myself—figuring out who we are serving, what the value chain looks like, and the unit economics of our business. After grasping these elements, I then pass this knowledge onto the team, allowing them to make their own decisions. Whether it's choosing which campaign might resonate, which customer insights to build on, or how much to spend on a project, I want the team to have the autonomy to decide these things for themselves.

Who is your ICP? And how did you identify them?

So let me describe our ICP first, then we'll talk about the process of ICP experimentation or expansion and contraction. Paddle serves self-serve digital product businesses who are selling globally. So self-serve means the price point is probably under $1000 a month for any given plan. So it's prosumer, consumer, or small SMB software—could be SaaS, could be AI, could be digital content, could be consumer apps selling on the web.

That ICP feels really big. But it's really important that we're specific; we have an acceptable use policy. And we, for example, don't do anything in gambling, don't do anything that's adult content, don't do anything that's financial advice, don't do anything that's pure consulting. There's a whole bunch of stuff that sits outside of that.

How do you build an ideal customer? Having done this for several businesses, I think the danger in the early days is you think way too broad. And normally, the process of going to market is around actually narrowing your target market again and again and again until you have real resonance with a small niche. I like the Geoffrey Moore “Crossing the chasm” framework. It's a bit overly militaristic, but in terms of his metaphor, you need to find one beach that's on one county that's in one part of a country that's on one side of a continent - before you actually start to expand.

And I think it's too easy to imagine this billion-dollar market and the piece you're going to take out of it, rather than grapple in detail with the next 10 people you've got to build relationships with. And so Paddle has gone through many stages of growing and shrinking our ideal customer list. Examples would be forays into trying to serve upmarket B2B companies and then retracting from that as we realize actually that's not our strength.

🚨 Merchant of Record, Digital River is winding down. Affected by this? Paddle can get you up and running in 48 hours.

How do you set goals?

At Paddle, we set goals in a structured manner, driven by the varied interests of our stakeholders which include VCs, PE funds, our founders, and the team. This diversity influences us to aggressively pursue creating substantial enterprise value. Our finance function leads the goal-setting process from a financial perspective, employing both top-down and bottom-up approaches to flesh out our revenue and cost planning. This involves crafting multiple financial scenarios to navigate our targets effectively.

Beyond just numbers, we have the Paddle Operating Plan, or POP, which forms the backbone of our strategic initiatives. This plan is built around five key strategic pillars that endure. Each initiative within these pillars is designed to be specific, measurable, and directly tied to our overall company strategy, managed by a dedicated team member who ensures these are not only planned but also executed across functional lines. This dual approach of rigorous financial planning combined with strategic operational goals allows us to remain focused and aligned as we scale our operations.

How do you build culture?

I believe that culture is what happens when no one is watching; it isn't an artifact on a wall. Our culture is frequently reflected back to us by our customers—it's helpful, humble, smart, and cross-functional. Over recent months, we've taken the initiative to formally document our culture, not as a mere static declaration but as a living set of values that guide our daily interactions.

We've distilled our culture into three straightforward statements: we paddle for others, we paddle together, and we paddle simply.

These principles aren’t just phrases; they're the tools we use every day to build and reinforce the culture at Paddle.

Detail your recruitment strategy. How do you hire All-Star talent?

We have an in-house talent acquisition team that drives our hiring, though we also work with external headhunters when needed. Every candidate goes through multiple interviews, covering both technical skills and cultural fit.

A big part of our success in attracting top talent comes from the employer brand we've built over the last three years. Last year alone, we hired 86 people out of 32,000 applicants—it’s incredibly competitive to get into Paddle.

This isn’t just because of our hiring process, but also because we’re highly visible in the market. We deliver strong results, we share what we’re working on, and we talk openly about our approach. I personally stay active on LinkedIn, and that alone brings in a steady flow of inbound applicants. Being present and engaged in the industry makes a huge difference in attracting top-tier talent.

Can you detail your process? What does it look like?

Because we get such a high volume of applications, our hiring process starts with an initial review by our talent team before the hiring manager gets involved. Once we’ve shortlisted candidates, the first interview focuses on technical fit—do they have the right skills and experience for the role? This stage is led by the hiring manager and relevant team members.

After that, we move to the values and cultural fit stage. At this point, we bring in people from other teams to get a cross-functional perspective. We want to ensure the candidate not only has the skills but also aligns with our company culture and values.

It’s important to us that we’re not just hiring great talent but hiring people who fit how we work at Paddle. There are plenty of incredibly skilled people who just might not be the right match for us—and that’s okay. This process helps us make sure we’re bringing in the right people for the long term.

Do you run hybrid, on-site or remote and why?

We’re remote-first but with a hub strategy. That means no one is required to be in an office, but we have physical hubs in key locations. Our largest hub is in London, where we were founded, and we also have hubs in Dublin, Amsterdam, Lisbon, Austin, and Toronto.

We hire within two hours of one of these hubs so that, while people work remotely, they can still meet up when needed. This setup allows us to bring teams together for end-of-quarter reviews, leadership meetings, or just general collaboration when key execs are in town.

It gives us the best of both worlds—remote flexibility while still having in-person moments that help strengthen relationships and culture.

How do you get the best out of yourself personally and professionally?

I’m a verbal processor, so I learn best by talking to people who are smarter than me. I listen to a lot of podcasts and read plenty of books, but my favorite way to learn is through conversations with people who have real, practical experience. That’s why I set aside time every week for external conversations—ones that aren’t tied to a specific business goal but help me learn about leadership, marketing, or the industry as a whole.

I also try to be mindful of how I structure my time. It’s easy to get caught in back-to-back Zoom meetings all day, so I make a conscious effort to avoid becoming a bottleneck. I delegate where I can and carve out space for deep work—whether that’s strategizing, thinking through big-picture challenges, or just taking a walk to reflect.

Variety also plays a big role for me. I travel a lot, and I try to keep my work dynamic, whether that’s working with different people, tackling new projects, or experimenting with fresh ideas. I know I stagnate if I’m doing the same thing for too long, so keeping things varied helps me stay engaged and effective.

Lastly, I believe in doubling down on strengths rather than fixing weaknesses. Instead of trying to turn my 3/10 skills into a 5, I focus on making my 7s and 8s into 9s and 10s. That’s where I can add the most value.

Is there anything I should have asked you? Something you do uniquely well?

There are a bunch of things, but one that stands out is how we think about experimentation in marketing. Two of my direct reports focus on keeping the marketing engine running—demand gen, product marketing, brand, all the things that drive the business day to day. But the third, Tharshan, is entirely focused on experimentation. His job is to take new ideas, run at them with very little structure, and see what has potential.

We always have multiple irons in the fire—things that aren’t fully baked yet but could turn into major parts of our go-to-market strategy. One of the best examples is our AI Launchpad. We saw a big wave of AI startups popping up and thought, ‘Wouldn’t it be cool to create an accelerator to support them and introduce them to Paddle?’ So Tharshan ran at it. The first cohort was 40 companies, a small marketing budget, and some AWS and Google Cloud credits as prizes. No big bets, just a test. Fast forward, and we’ve now incubated 250 AI startups across three cohorts. Founders apply ahead of time because they know the value, and it’s become something we’ll keep running and scaling.

This kind of approach lets us test new things without messing with the core marketing engine. Some bets don’t work, but the ones that do can become huge growth levers for us. And I think that’s really important—keeping that balance between executing what we know works and always pushing for what might work next.

And that’s it! You can follow Andrew on LinkedIn and also checkout Paddle on their website to learn more.

BRAIN FOOD 🧠 

Since we’re on a startups, this week I watched this video on how you can use AI to start your own startup. If you've ever toyed with the idea of starting a new thing—maybe an AI venture, this episode from Y Combinator is a goldmine.

TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️

Every week we highlight tools we actually use inside of our business and give them an honest review. Today we are highlighting Attio—powerful, flexible and data-driven, the exact CRM your business needs.

See the full set of tools we use inside of Athyna & Open Source CEO here.

HOW I CAN HELP 🥳

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