Oakland Roots Takes AI from Experimentation to Everyday Work with trnsfrmAItn
Executive summary
Oakland Roots Sports Club, an American professional soccer club, saw an opportunity to use AI to help its teams work more efficiently and create more time for strategic and creative work. But AI use across the organization was still informal, with only a handful of employees experimenting independently and no established approach for organization-wide adoption.
Working with trnsfrmAItn, Oakland Roots strengthened its approach to responsible AI use and introduced a three-part learning experience that combined AI fundamentals, practical tool training, and the AI Trail, a 30-day program designed to turn learning into everyday habits.
Today, the vast majority of staff are using AI in their daily work, experimenting with new use cases and automations, and finding ways to turn work that once took hours into minutes.
Finding an edge with AI
In professional sports, teams are constantly looking for an advantage. For Oakland Roots, that extends beyond what happens on the field. “Sports is an extremely competitive industry, on and off the field, and we look for every advantage we can get,” says Lindsay Barenz, President at Oakland Roots. “AI tools have become accessible and affordable enough that it made sense to move from individual experimentation to organization-wide adoption. We want to be the most technology-forward club in our league.”
The potential value was easy to see. As a growing organization with a lean staff, Oakland Roots believed AI could help employees spend less time on routine work and more time on the creative and strategic work where their expertise matters most. “The most immediate benefit is efficiency,” Barenz says. “With proper human oversight, routine tasks can be delegated to AI tools, which frees our staff for higher-value creative and strategic work.”
But before the engagement with trnsfrmAItn, adoption was happening unevenly. “AI use was informal and limited to a few early adopters working on their own,” Barenz says.
AI use was informal and limited to a few early adopters working on their own.
Lindsay Barenz, President, Oakland Roots
The organization also needed clearer guidance around responsible AI use and guardrails. That’s when trnsfrmAItn guided the club to establish approved AI tools so employees could experiment within appropriate guardrails, and implement a clear AI use policy to help staff understand how to use AI appropriately, safely and responsibly.
The next challenge was helping people actually use it.
Moving beyond the AI hype
For Edreece Arghandiwal, Chief Marketing Officer and Co-Founder of Oakland Roots, the goal was to not just introduce another piece of technology, but to make AI become useful in the reality of their employees’ work. “Honestly, I wanted to get past the hype. Everyone’s talking about AI, but I wanted our team to actually know how to use it in our day-to-day, not just play with it.”
Rather than relying on a one-time prompting workshop or tool demonstration, Oakland Roots and trnsfrmAItn adopted a three-phase approach designed to build understanding, practical skills and lasting habits.
AI 101
(AI foundations)
Tech 101
(Tool training)
AI Trail
(Habit building)
The experience started with an AI 101 workshop, which introduced employees to the value of generative AI, foundational prompting techniques, workflow possibilities, and ways to begin making AI part of their routines. For Arghandiwal, the biggest shift he experienced during that training was in how he thought about AI. “The mindset piece hit for me. Kristin framed AI as something you reach for first, not last, and that flipped how I approach a blank page.”
Learning the prompting best practices and shifting into an AI mindset also changed the team’s understanding of what it takes to get useful results from AI. “Seeing how much better the output gets when you give real context made it click that the quality of what you get back is on you,” Arghandiwal says.
Adrian Ghilardi, Account Executive for Ticket Sales & Service at Oakland Roots saw a similar challenge. AI outputs had often been close to what he needed, but not useful enough to justify the use. Learning how to construct and refine prompts changed that. “The basics of prompting lesson was very helpful as it helped me properly refine my outputs,” Ghilardi says.
The second phase was a customized Tech 101 workshop. Instead of providing generic tool demos and prompts, trnsfrmAItn tailored the examples to real use cases Oakland Roots employees encounter every day.
Lucas Ruiz Brockl, Coordinator for Brand Partnerships, came into the experience wanting to move beyond using AI primarily for email editing and grammar correction. “I wanted to identify daily tasks where I could save time,” Ruiz Brockl says. “The session showed me how to efficiently analyze large chunks of performance data to deliver an analysis to our partners.” Through the training, he began seeing opportunities to deliver better insights to partners and reduce the manual work involved in tracking partner deliverables.
For Ghilardi, the workshop made AI feel more accessible and relevant to his everyday work. “The Tech 101 session helped me approach AI use with less trepidation.”
But one-time training doesn’t create lasting change, so the next step for Oakland Roots was making those new skills stick.
From AI learning to AI habits
After foundational and tool-focused training, employees moved into the AI Trail, trnsfrmAItn’s proprietary 30-day experience built around daily prompts, use cases, tips, and challenges that employees can incorporate into everyday work.
For Arghandiwal, extending the experience beyond the initial workshops made a fundamental difference. “A one-time training is fun, but then you go back to your old habits on Monday. The AI Trail made us show up every day for a month, and that’s how habits actually form.”
A one-time training is fun, but then you go back to your old habits on Monday. The AI Trail made us show up every day for a month, and that's how habits actually form.
Edreece Arghandiwal, Chief Marketing Officer and Co-Founder, Oakland Roots
The daily challenges were small enough to incorporate into work rather than compete with it. “By the end of the AI Trail, using AI felt normal instead of like an extra step,” Arghandiwal says.
Ruiz Brockl also saw value in having time to put new skills into practice. “A 30-day experience is more impactful because you can integrate new skills into your day-to-day work in real time. When new problems arise, you can utilize the skills you are learning in the moment.”
The flexibility of the program also meant that not everyone engaged in exactly the same way. Ghilardi preferred working through the AI Trail in larger chunks, reinforcing the value of a learning experience that gave employees room to engage at their own pace. He also saw that sustained approach as particularly useful for people who might otherwise be intimidated by AI. “The 30-day approach especially keeps the less tech-savvy from being intimidated or overwhelmed,” Ghilardi says, describing that as one of the biggest potential barriers to AI implementation in the workplace.
Turning hours into minutes
As employees became more comfortable experimenting with AI, new applications also began emerging across the organization. Arghandiwal now uses AI for work ranging from partner recaps and campaign briefs to pushing early ideas further. He has used it to develop first drafts of match-day email campaigns, summarize lengthy partner conversations before calls, and extract insights from ticketing spreadsheets. More recently, AI helped consolidate and summarize feedback from the club’s NPS surveys, supporting efforts to improve the game-day experience. “What used to take me hours now takes minutes,” says Arghandiwal.
Ruiz Brockl has become more intentional about writing prompts and saves successful prompts for future use, while Ghilardi is using AI for bulk data manipulation and formatting.
AI adoption is now widespread and a large majority of our staff are using AI tools in their daily work.
Lindsay Barenz, President, Oakland Roots
Those individual changes have added up to a broader shift in how Oakland Roots approaches AI. “Adoption is now widespread and the large majority of our staff are using AI tools in their daily work,” Barenz says. “Critically, we also have clear guardrails defining appropriate and responsible AI use.”
Transforming how Oakland Roots operates with AI
For Oakland Roots, the journey was not about getting every employee to use AI in exactly the same way. It was about creating the foundation that allowed people with different roles, needs, and levels of AI experience to discover where the technology could make their own work better.
“What stood out was the flexibility,” Barenz says. “trnsfrmAItn combines in-person training with a self-paced digital program, so staff can learn in whatever way works best for them. That mattered for us, because our staff started at very different levels of comfort with AI.”
If you’re a lean team trying to move fast without burning people out, this is a dope way to get everyone using AI with intention.
Edreece Arghandiwal, Chief Marketing Officer and Co-Founder, Oakland Roots
That combination of foundations, practical application, responsible use, and sustained learning helped move AI from experimentation by a few employees toward something used across the organization.
For Arghandiwal, that is what made the approach work. “Kristin made it approachable for everyone on our team, not just the tech-curious folks, and the 30-day structure is what made it stick,” he says. “If you’re a lean team trying to move fast without burning people out, this is a dope way to get everyone using AI with intention.”