Wes participated in this conversation in a personal capacity. All views are his own.
The retail media industry is moving at a breakneck pace, but while the technology scales, the talent pipeline is hitting a massive bottleneck. We are operating in an environment where expectations for perfection are higher than ever, yet there is no "Retail Media School" to prepare the next generation of leaders. If we don’t figure out how to bridge the gap between entry-level tasks and high-level strategy, we risk a total collapse of upward mobility in the modern workforce.
In this episode, we sit down with Wes, a Director of Media at a retail media agency, to discuss the "softer side" of the industry. We get into his unique "side door" entry into the field from a 15-year career in professional photography and how systematic mindsets translate across disciplines. We explore the rise of "Walmazon" as Walmart and Amazon begin to mirror one another’s strategies, the tactical necessity of clear summarization over AI-generated "novels," and the high-stakes reality of managed service vs. self-serve social tools. Wes shares his unique philosophy on why managers must find their own replacements to move up and the "aha" moment that led him to prioritize humility over individual wins.
The unglamorous truth is that AI might be able to handle menial tasks, but it cannot replace the "boots-on-the-ground" experience of walking a store floor or understanding a shopper's psychology. There is a real danger in over-relying on automation; if you turn in work without validating it, you aren't saving time, you’re devaluing your own expertise. You will walk away from this conversation with a fresh perspective on how to take initiative in your own career development and a warning about why "the way we've always done it" is already out of date.
More About this Episode
The Human Element in the Age of Retail Media Automation
Retail media is currently moving at a speed that often feels like it is outrunning our ability to organize it. We see the headlines every day about new self serve tools and AI powered optimizations. While the technology is fascinating, the real conversation we need to be having is about the people behind the consoles. Over the last few years, the trajectory of this industry has been incredibly steep. Expectations are sky high, and the work is becoming infinitely more complex. We are in a unique position where the tactics are expanding, yet there is no official retail media school. Most of us are learning on the fly, building the plane while it is in the air. This reality makes the intersection of talent, AI, and organizational relationships the most critical piece of the puzzle for any brand or agency looking to succeed today.
Breaking the Mold with Non Traditional Talent
One of the most interesting aspects of the retail media world is that almost nobody started here. Because the industry is so young, the talent pool is naturally comprised of people from non traditional backgrounds. I have seen photographers, teachers, and small business owners transition into retail media and become absolute powerhouses. The reason for this is simple: retail media requires a systematic mindset and a high level of curiosity rather than just a specific degree.
Consider a professional photographer. On the surface, their work seems purely creative, but it is actually deeply rooted in data and optimization. They are constantly adjusting white balance, exposure, and aperture based on shifting environments. When a photographer transitions into managing a retail media network, they apply that same iterative mindset to keyword optimization and bid management. They are used to creating a database in their mind of what works and what does not. This curiosity and willingness to fix things are the traits that truly matter. We should be looking for people who are hungry and willing to do whatever it takes to win, rather than those who simply check every box on a traditional marketing resume.
The Myth of Perfection and the Need for Humility
In this business, especially on the agency side or when presenting to retail giants like Walmart, there is an underlying expectation that you cannot miss. There is often very little grace for errors. However, when we bring in fresh talent, we have to recognize that their previous reference for success was likely a grade in school where 60% or 70% was a pass. In the professional environment, the goal is 100% accuracy, but getting there is impossible as an individual.
This is where humility becomes a foundational skill. Humility in retail media means being okay with proposing a strategy that you think is perfect, only to have your team pick it apart and find the flaws. It is about stopping the search for individual wins and starting to view a better team outcome as your personal victory. You develop this trait by doing it over and over again, failing, and learning that the team is the only way to reach that 100% threshold. As leaders, we need to foster an environment where people feel safe enough to be humble, knowing that the collective intelligence of the group is our greatest asset.
The Evolution of Training and Onboarding
The way we train people has changed drastically from the pre internet era. Gone are the days of a year long apprenticeship in the mailroom before you ever spoke to a client. Today, companies simply do not have the patience or the budget for that kind of hand holding. Furthermore, the industry moves so fast that a training manual written in January is often obsolete by June. This creates a shared responsibility between the organization and the individual.
Companies must provide the foundation, but the candidate has to have the initiative to dive headfirst into the data. I often tell new hires to get their certifications out of the way to understand the mechanics, but then they need to start poking around in the company drive and developing a point of view. However, there is a gap in our industry. We lack a sandbox environment. Most retail media platforms are paywalled and private, making it hard for newcomers to learn the hands to keys work without risking actual brand dollars. Until we have a universal simulation tool, the best training remains intentional shadowing and a relentless commitment to self education.
AI as an Amplifier Not a Replacement
There is a lot of talk about AI driving efficiency and allowing humans to do more with less time. While that is true in a sense, I do not believe AI makes anyone better at their job at their core. Only a human can make themselves better. What AI does is increase output and volume. It can churn through the tedious, minute tasks that used to take up a whole week. But there is a dark side to this: the accountability gap.
If an employee uses AI to generate a week’s worth of work in a single day and turns it in without validating the data, they have actually devalued themselves. The value of a human in the AI age is the ability to stand by the accuracy of the output. I do not care how my team gets the work done, but I do care that the work is complete and accurate. AI should be used to open up thinking time and strategy time, not just to pack more tasks into a day. If we use AI to eliminate entry level roles, we are essentially buying Peter to pay Paul. We would be sacrificing the future leadership pipeline for a short term gain in productivity. Without entry level roles, there is no one for the mid level managers to train, and without training others, those managers can never move up.
The Power of Clear Communication
If I had to identify the most undervalued skill in retail media today, it would be the ability to write and summarize clearly. We are inundated with data, and the temptation is always to write a novel to explain a trend. But the reality is that leadership does not want a novel. They have 150 other things to worry about. If you want someone to ignore your update, make it long and rambling. If you want them to pay attention, you have to shrink it down to its most vital parts.
The golden goose of talent is the person who can look at a complex data set or a long discussion and provide the perfect articulation of what actually happened. This requires a level of critical thinking that AI cannot yet replicate without heavy human guidance. Whether you are just starting out or you are a seasoned director, your ability to describe what is going on concisely is what will ultimately define your success.
Looking Ahead to the New Retail Landscape
As we watch Walmart expand its social media capabilities and Amazon experiment with AI powered physical stores, it is clear that the lines between digital and physical shopping are blurring. We are entering the era of the Walmazon, where the logistics of one and the digital prowess of the other are merging into a single consumer experience. In this environment, the winners will not just be those with the best algorithms, but those with the best people capable of orchestrating those algorithms.
The skills of the future are the soft skills that have always mattered: curiosity, humility, and the ability to build relationships. We might eventually have digital twins of ourselves attending meetings, but we will still need real human connections to drive strategy and innovation. Retail media is a fast trajectory industry, and while the technology is the engine, the talent remains the driver. We must continue to invest in people who can think critically, communicate clearly, and maintain the humility to grow alongside the machines.
