The footage wasn’t supposed to be an ad.
It was raw footage for a welcome video, the kind of thing a new member watches on day one. But when Akshay Sud, Senior Performance Marketing Manager at MasterClass, watched it back, something in it stopped him.
In it, MasterClass’s founder and CEO tells a story about Aristotle devoting himself fully to one student, who became Alexander the Great. Akshay pitched it as an ad anyway.
It was the first time in MasterClass history a founder had appeared in paid creative, and nobody was sure it would work. It became one of the strongest performers of the year.
That story is a good one, but it’s not the only point of this conversation with Akshay.
The point is what Akshay does after a story like that lands: how he separates what got attention from what actually drove the result, why he thinks most teams misread their own wins, and what he’d tell a small agency team trying to build their first real testing system.
If you’re in Vancouver, you’ll get to hear more of this thinking in person.
Akshay is hosting one of five table conversations at the Agency Together Mastermind Mingler on September 17th, walking through how to turn one good ad into a system that keeps producing winners. Registration closes September 14th.
Akshay Sud
Q: You’re a Senior Performance Marketing Manager at MasterClass. In plain terms, what does a normal week look like for you when it comes to creative and testing?
Chaotic in the best possible way.
My role sits at the intersection of paid media, creative strategy, data, and product marketing. On any given week I’m analysing full-funnel performance data, working with creative teams on concepts and executions, syncing with product and data partners to piece together what the numbers are actually telling us, and then figuring out how to translate all of that into the next brief. It sounds like a lot because it is, but that’s also what makes it genuinely fun.
Right now a huge focus is MasterClass Executive, which is a first-of-its-kind AI-native business program we launched earlier this year, built in collaboration with the University of Chicago Booth School of Business and OpenAI. It’s designed to help senior leaders navigate and lead through the AI era. Launching something this new, this different from anything MasterClass has done before, means we are essentially building the playbook as we go. Finding product-market fit, figuring out how to position something the market has never seen, understanding who our audience really is versus who we assumed it would be. That last part has been the biggest surprise, honestly. Some of our strongest signals have come from audiences we never planned for in our initial strategy. The data humbled us quickly, and we are better for it.
Q: Let’s ground this in something real. Can you walk us through one ad or campaign from this year that really worked, without giving away anything proprietary? What was it, and what made it stand out?
Because MasterClass Executive was such a new and different product, the creative challenge wasn’t just “how do we make a good ad.” It was more fundamental than that. We had to answer why this product exists, who it’s genuinely for, and why only MasterClass could make it. Those are the questions you have to answer before any creative brief makes sense.
One campaign did that better than anything else we ran. And funnily enough, it was never supposed to be an ad.
The original footage was shot for the program’s welcome video, the kind of thing new members watch on day one. But when I watched it back, something clicked. Our founder and CEO was telling a story about Aristotle. The idea being that Aristotle devoted everything to one student, gave that student his complete attention and wisdom, and that student became Alexander the Great. His point was that this kind of access, a world-class mind fully invested in your growth, basically doesn’t exist anymore. And MasterClass Executive is trying to change that.
I pitched it as an ad. The honest internal reaction was somewhere between intrigued and uncertain. It was the first time in MasterClass history that our founder appeared in paid creative. Nobody was sure it would work. I’m glad we had leadership willing to trust the instinct and give us the room to try something that had never been done at the company before.
It worked because it didn’t lead with the product. It led with an identity. Not what you would learn, but who you could become. For an audience of senior professionals who feel like they’ve hit a ceiling, that emotional truth landed harder than any feature we could have led with.
Q: You talk about winning ads as data points rather than destinations. What does that actually mean in practice, and why do most teams miss it?
When an ad performs well the instinct is to immediately make more of it. More founder videos. More historical references. More of whatever you think you saw. But that’s not understanding why it worked. That’s just copying the surface and hoping the result follows.
The way I think about it is that a winning ad is a hypothesis that just got confirmed by the market. Encoded inside it is something the audience told you.
A tension that felt real. An argument that landed. A feeling that moved them before they even realised it. Your job is not to copy the ad. Your job is to decode what the market told you and build something that lets you test that signal further and faster.
In practice that meant going back to the Aristotle ad and separating what we observed from what we actually believed drove the result. We landed on the angle as the real driver. Not the format, not the founder’s presence specifically, but the identity transformation underneath everything. Who you become, not what you learn.
That became the foundation for what we tested next. Not “make more ads like this one” but “does this argument extend beyond this specific story?” Those are completely different questions. Only one of them compounds.
Most teams miss this step because celebrating a win feels better than dissecting one. Which is understandable. But the teams that stop and ask why, every single time, are the ones that get sharper each sprint instead of restarting the clock.
Q: What’s a mistake you’ve seen teams make when they get a winning ad?
Crediting the most visible thing. The founder ad worked so founder content becomes the strategy. Ten more get briefed. Some perform, some don’t, and nobody can explain the difference because too many things changed at once.
Here’s the thing about creative performance: visibility is not causality. The most memorable element of an ad is not always what drove the conversion.
You have to be willing to be wrong about what you think you know, which is harder than it sounds when you’re the one who wrote the brief.
The other mistake, which is sneakier, is writing the brief after the concept already exists. The idea comes from a brainstorm or a competitor ad someone screenshotted, and then the brief gets written around it to make the process look more strategic than it was. That brief can never teach you anything because it was never a real prediction. You can’t confirm or reject a hypothesis you invented after seeing the result.
Q: What does the feedback loop between creative, data, and the next brief actually look like in practice?
It only works if everyone is operating from the same information at the same time. What kills most feedback loops is creative and media working in parallel but not actually talking, or creative teams never seeing the performance data at all. Which, again, happens more than this industry likes to admit.
The discipline we try to maintain is ending every sprint with three things documented. What we tested and why. What happened. And most importantly, what we now know about the audience that we didn’t know before.
That third one is where most teams check out. It’s also the only sentence that actually travels into the next brief. Without it you have a result. With it you have a learning. A result tells you what to report. A learning tells you what to brief next. They sound similar but they compound very differently.
Q: If you were advising a small agency team on building a real testing system, where would you tell them to start?
The brief. Not the creative, not the reporting, not the testing cadence. The brief.
Most agency briefs are production orders dressed up as strategy. Audience, message, format, deadline. They describe what to make but not what to test. When results come back there is nothing to compare them against except gut feel, which is a terrible place to base the next brief.
The single highest leverage thing a small team can do is get into the habit of finishing this sentence before anything goes into production: we believe this specific audience will do this specific thing when they see this specific creative, because it names something they have felt but never seen stated directly, and we will know it worked if this metric moves.
If you can finish that sentence, you are running a test. If you cannot, you are running a production cycle and hoping something sticks. The difference sounds small. The compounding effect over time is not.
Q: How do you talk to clients about creative performance in a way that’s clear and doesn’t feel like jargon?
I think about my job in pretty simple terms. I use the principles of persuasion and human psychology to help people recognise how a product can positively impact their lives, and then make them want to act on it. When I keep that definition in my head it makes client conversations a lot cleaner.
Instead of leading with metrics I try to lead with questions.
Not “CTR was 3.2 percent” but “we wanted to understand whether this audience responds to aspiration or urgency, and here is what we found.” Clients understand questions. They understand findings. What they struggle with is a dashboard full of numbers that doesn’t tell them what to do next.
The other thing that actually builds trust, and this surprises people, is being upfront about what you don’t know yet. Most agency presentations are performances of confidence. The conversations that land are the ones where you say: here is what we confirmed, here is what we still need to figure out, and here is why that matters for next sprint. That’s a real conversation. Everything else is a slide deck people sit through.
Q: What’s one thing agencies often get wrong when they pitch “creative testing” to clients?
They pitch volume. More creative, more variants, more testing. The promise is that if you run enough things something will work.
The problem is that volume without structure is just expensive guessing.
Running ten ads with ten different angles tells you which one won. It tells you nothing about why. And if you don’t know why, the next brief is no smarter than the last one.
What agencies should be selling is better questions, not more content.
If you can sit across from a client after six sprints and say we now know which emotional argument converts your specific buyer, and why, and what to test next, that is a completely different value proposition.
One of those helps move a client’s business forward. The other just keeps billing them.
Q: If an agency owner takes away just one idea from this conversation, what would you want it to be?
The platform can tell you what won. It cannot tell you why. Why is the only thing that compounds.
Most agencies are very good at reporting what won. Dashboards, weekly calls, performance summaries. What mostly goes unanswered is why something actually worked at the level of what the audience felt in the moment before they converted.
The teams that answer that question consistently, and document it in a way the next brief can actually use, are the ones that get meaningfully better every sprint. Not because they have better instincts than everyone else. Because they built a system that learns. And in this industry, a system that learns is the only unfair advantage that’s completely free to build.
Want to keep the conversation going?
Come do this in person. The Agency Together Mastermind Mingler is a curated evening for founder-led agencies in Vancouver, September 17th, 4:30 to 7:00 PM. Akshay is one of five table hosts, and conversations like this one happen live, around a table, choose-your-own-adventure style.
45 seats. Registration closes September 14th.
Get your ticket: https://agencytogether.com/mastermind-mingler
