Failure isn't final - it's feedback. This perspective has never been more relevant than in the fast-paced world of retail media, where even the most seasoned professionals encounter significant setbacks on their path to success.

I recently connected with several brand-side retail media leaders to discuss those pivotal moments when their initial strategies fell flat. What emerged was a fascinating collection of stories about product reformulations gone sideways, agency transitions that crashed before succeeding, budget-draining category takeovers, and critical communication failures. But more importantly, these conversations revealed how these initial failures became the foundation for their eventual success.

The insights these leaders shared demonstrate that in retail media, sometimes you need to fail spectacularly before you can succeed strategically. Their experiences offer valuable lessons for anyone navigating the complex retail media landscape.

When Your Playbook Doesn't Work

Justin Bomberowitz, Director of Ecommerce at WILDE Brands, shared a humbling experience from his time at SmartSweets. "I always thought that when I get in, I could put a playbook together and Amazon would go up," he explained. However, after joining the company in 2021 following a product reformulation, he quickly discovered that the existing playbook wasn't working.

"We had to scrap it completely and start again," Bomberowitz admits. This required extensive collaboration across the organization, "holding hands with a lot of people - our co-manufacturers, our co-packers, the board executives, everyone down to writing content and creating SKUs."

The key lesson? "There's not just one playbook for Amazon... you have to have a couple of options." This flexibility and willingness to pivot when strategies aren't working has become a cornerstone of his approach to retail media.

Second Time's the Charm with Agency Partnerships

Jamie Roller, Director of Marketplaces at Dr. Squatch, described a recent agency transition that initially went "absolutely horribly." After moving away from an algorithmic solution that was delivering acceptable results, they found themselves in a situation where "results were terrible" and the process felt like "a black box."

Despite this initial failure, Roller and her team remained convinced they needed to make a change. After thoroughly vetting new agencies and SaaS vendors, they found the right partner and implemented a more gradual transition. Jamie says that the results were worth it. "After several months, they were absolutely astounding," she said.

Her experience resulted in two key takeaways: "You need to make the transition slowly, and you really need to have the right partner who's a fit for your goals, not just a partner who's had good referrals." Sometimes, success requires a second attempt with better preparation and partners.

Rethinking Your Funnel Strategy

Nemanja Lazic, E-Commerce Channel Manager at Zevia, recounted an Instacart campaign that "just kind of blew up on us." The broad, category takeover campaign aimed at building brand awareness ultimately delivered negligible ROI, terrible click-through rates, and quickly depleted their budget.

"We served a ton of impressions to very, very uninterested eyeballs," Nem says. This failure prompted a strategic reassessment: "Maybe we don't need to go that high up the funnel... maybe the distribution is not there. Maybe the shelf space just isn't there."

The team pivoted to focus "energies a little bit more downstream" where they could "really win over that conversion." This experience taught Nem to align his campaign strategies with their current brand position and digital shelf presence rather than overreaching with upper-funnel activations before they were ready.

Beyond the Work: Managing Up and Building Your Brand

Julie Liu, Director of Digital Commerce at Ghirardelli Chocolate Company, offered a different perspective on failure and success - one focused on career advancement. "Each time I was unsuccessful [in seeking a promotion], it was because I was hoping that my work would speak for itself," she reflects.

Julie discovered that success came when she "stopped focusing on working hard or working long hours, but really focused on working smarter." This meant ensuring her work and impact were visible to the organization through proactive conversations about growth and relationship-building, not just with her boss but with her "boss's peers."

"Just knowing how often digital and e-comm tend to shift around in organizations, I realized that it was really important to think about who my future boss could be," Liu explains. Her approach emphasizes the importance of personal branding within a company - building your reputation beyond your immediate team.

I shared with Julie a strategy I've heard from Todd Hassenfelt at Colgate-Palmolive: creating a regular email communication about news and trends in the space and distributing it across the organization. This approach not only educates colleagues but raises your profile in a meaningful way beyond your direct reporting line.

The Bottom Line

These stories of failure and recovery reveal a common thread: resilience and adaptability are non-negotiable skills in retail media. Whether it's scrapping a failing playbook, trying again with a better agency partner, recalibrating your funnel strategy, or improving how you communicate your value, the path to success often includes detours through failure.

The next time you face a setback in your retail media efforts, remember these leaders' experiences. Your initial failure might just be the foundation for your next breakthrough strategy - as long as you're willing to learn, adapt, and try again.