AI Upskilling: How We Built and Trained an AI-Powered Creative Team

Published Jun 5
Eden Laboda
Eden LabodaEmployer Marketing Manager, Superside

Generative AI is already transforming how creative teams work. As teams embrace AI, upskilling is just as essential as the tech stack you choose. In this article, Superside's Employee Marketing Manager, Eden Laboda shares how Superside trains and empowers its world-class AI creative team. Discover the lessons learned along the way and how the learning continues.

We hire the top 1% of creative talent. This simple phrase isn't just a marketing statement—it drives our talent strategy, from our hiring processes to career development.

Upskilling is not only a corporate social responsibility, it’s a crucial strategic initiative.

With generative AI disrupting the creative industry, Superside recognized the need to integrate it into our creative processes, seizing opportunities and passing these advantages directly to our customers.

How do you create a learning program when you don’t know much about the future? Technology is moving faster than ever, and the only thing we’re sure of is that things will never be the same. It’s no longer a question of when to start—it is a question of how to start.

This article explores how we upskilled and enabled our AI-powered creative teams, highlighting our journey and the ongoing evolution of our AI initiatives.

What's Upskilling in the Age of AI?

It’s not just learning how to use another tool, with generative AI your workflow is totally different. You’re rethinking how you create design.

Aki Friedrich
Aki FriedrichDirector of Learning Experience, Superside

Learning new skills allows workers to adapt to transformation. Upskilling or reskilling goes beyond standard training. It serves a strategic skills shortage or an important shift within an industry. It’s more complex and often more costly, but it's also essential to driving business transformation.

From an organizational perspective, it requires a change management initiative involving clear leadership support and strong worker engagement. Reskilling becomes part of an ecosystem rather than an individual.

Building an AI Intelligentsia

Understanding generative AI, its application in graphic design and copywriting, knowing which tools and platforms to prioritize, and developing and implementing processes and workflows that work internally and with customers all require research, testing, experimenting, and adjusting.

Just like everyone else, we are learning as the technology is being developed. Things are changing quickly, resources are still scarce, and often, they are already obsolete.

Having a dedicated team of specialists has proven to be a game-changer for Superside. They built our path to providing generative AI Services, cutting through the noise and setting up knowledge libraries, resources, and best practices.

5 Action Points for Adopting AI

Superside's Generative AI Team built a philosophy for adopting AI that revolves around 5 action points:

  • Get comfortable experimenting with new AI tools and methods.
  • Invest in developing a systemic approach to integrating the most appropriate tools into your workflows.
  • Understand the foundations and constant evolution of generative AI to make informed decisions.
  • Make adaptability your #1 skill to master in this rapidly evolving landscape.
  • Focus on mastering things that are stable.

This also contributed to reinforcing a positive team environment where challenging the status quo, coming up with new ideas, and voicing half-finished thoughts felt very safe.

Once workflows, processes and tools were developed and selected, the Learning & Development Team could build a learning journey adapted to upskill all our creatives.

Developing an AI Upskilling Program

Our top priority was to avoid any knowledge/implementation gap. The upskilling program needed to empower creatives to apply their new knowledge directly in the customer projects and develop their flexibility to continue adopting new technologies even after the training program was done.

With that in mind, the Learning Experience Team developed a six-week program with self-exploration and practice at the center. We wanted to mimic real-life situations that let students figure things out on their own without limited intervention from the coaches.

Key Components of Our AI Upskilling Program

An effective AI training program is more than just the tools you're training on, you also have to consider what the participants will need to gain mastery of today's tools and long-term proficiency as the ecosystem advances.

AI tools and platforms

The tools and technologies surrounding generative AI will continue to evolve. Instead of focusing on mastering any single tool, our course offers practice with AI tools like ChatGPT and Midjourney, which are intended to develop a broader spectrum of skills like prompting or selecting the right parameters for the effect you want to achieve.

More than learning a tool, finding ways to apply AI effectively requires a new mindset, problem-solving skills, and hands-on experience—all developed through application.

The fundamental goal of our program was a mindset shift rather than onboarding a tool.


Generative AI evolves faster than resources are created, and the amount of tech being made is also enormous. These resources needed to be curated, ensuring they were up-to-date and adequate. Many resources didn’t exist, and we needed to create them through short tutorials, best practices videos, and other how-tos.


As we mentioned earlier, practice is at the core of the journey. Multiple projects are done to ensure that designers can apply what they have learned directly. The projects get more complex over time and closer to real customer cases with a specific amount of time allocated to each one. This aims to simulate real-life experiences where our creatives must work within preset time constraints.


I would estimate that a good ratio for support learners is 20%-30% guidance and 70-80% exploration space.

Aki Friedrich
Aki FriedrichDirector of Learning Experience, Superside

Although we want to empower learners to explore independently, we must still facilitate the learning process. Each learner is guided by a coach from the Generative AI Team who provides extensive feedback and ensures that results are on par with our quality control. One of the coach's key responsibilities is supporting creatives in finding solutions to their problems. This drives a huge increase in our engagement rate, as mentors can address concerns and challenges once a week.

Social learning

We created and put a lot of emphasis on our Generative AI dedicated community Slack channel. We wanted our creatives to learn from each other, develop knowledge sharing, and give everyone the feeling that we are in this together.

Deploying an Upskilling Program

While we pulled our pilot program together in two weeks, the maturation of the program is very much an iterative process.

A pilot built in two weeks

In two weeks, yes, but this was only possible because of the extensive work our Generative AI Team was able to do before creating the pilot and a dedicated Learning Experience Designer working on it full time. Allocating these resources was key to such a short timeline.

The Learning & Development Team selected approximately 10 creatives with differing capabilities to follow the course, keeping an eye on the engagement rate, gathering feedback, and assessing project quality

An iterative journey

Streamlining communication was very important. We quickly knew what wasn’t working and could adapt, change, and optimize the course. Some fixes were done within a few hours.

Indre ​Lukauskaite
Indre ​LukauskaiteLearning Experience Designer, Superside

Building AI design skills is not a step-by-step flow. The Learning & Development Team keeps close contact with everyone on their learning journey, chatting with many participants daily.

Every new upskilling cohort benefited from this iterative approach. The substance didn’t change much, but making sure people understood instructions clearly was a constant focus. Keeping close communication also helped learners to keep engaged and motivated to stay on the journey.

Overcoming Challenges in AI Upskilling

The challenges of creating an entirely new training program are more than developing lesson plans and grading performance, including fostering interest in the first place and planning for the learning itself to be ongoing.

Resistance to change and adoption of new technologies

Paradoxically enough, the main barrier to AI adoption isn’t technical, it is human. Companies often build a business framework for change management, gathering data, evaluation capabilities, and charts. But just as often, they forget the time needed to bring people along, address their fears and concerns, and build excitement and confidence.

Adopting new technologies goes fairly smoothly with the right learning journey, a process that's eased by:

  • Giving clear guidance and direction. Explain how and why you are adopting AI. Help employees understand what the future will look like, what steps you are taking to get there, and set expectations.
  • Focusing on positive emotions. Inspire excitement and confidence—sentiments that are more effective for long-term change. Communicate how AI benefits them, their career, and their creativity. Tapping into their emotional desire is more likely to make it part of someone's identity.
  • Shaping the right environment. Create an environment where AI is everywhere. Continuous exposure will make generative AI more familiar and more likely to be adopted.

Initial learning curve and time investment

Upskilling in AI comes with its learning curve. Creatives not only learn new tools, but they also learn new ways of thinking and creating. This can make someone feel like they’re going slower or less efficiently before they can leverage the power of AI and go faster in their creativity.

The philosophy is to embrace the learning process by directly applying generative AI (GenAI) tools in their creative work, even if it initially feels slower or more challenging. We need to get comfortable with uncertainty, experimentation, and taking the time to master a tool and method.

It should be clear that investing this time is beneficial. Using social proof can help you advocate for the larger community. In our case, seeing people successfully finish the course and get onboarded to AI-Enhanced Projects for customers created excitement, fear of missing out, and quick word of mouth among our creatives. The engagement rate shifted gradually at first and then extensively with each cohort.

What the Future Holds

As generative AI continues to evolve, we anticipate further innovations impacting the creative industry. By empowering our creatives with the latest AI tools and upskilling, we are future-proofing our team and delivering unparalleled value to our customers.

Our journey with generative AI is an ongoing one, and far from over. We continue to refine our upskilling programs taking into account the latest AI advancements, our customers’ needs, and business developments to ensure our team remains at the cutting edge of the industry.

Get Your Team AI-Powered Even Faster
Get Your Team AI-Powered Even Faster

Get Your Team AI-Powered Even Faster

An extension of your team, Superside expands capacity with AI-Enhanced Creative Services and helps you lay the foundations for success with AI Consulting, including upskilling.

Eden Laboda
Eden LabodaEmployer Marketing Manager, Superside

As Superside's Employer Marketing Manager, Eden Laboda combines her digital marketing background and her passion for organizational culture to help attract the top 1% of global talent. Connect with Eden on LinkedIn and learn more about Careers at Superside.

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