How Sidearm Sports built an AI-first culture by starting at the top and refusing to stop until it reached every corner of the organization.
George Scott, Sidearm Sports president, didn't come to AI through a corporate initiative. He came to it the way most early adopters do – on his own, figuring it out, getting frustrated, and eventually getting hooked.
It started in early 2024 with data analytics. The first results were a mess. But once he worked through it, the potential was obvious. He started taking classes. He went to a small leadership summit where he heard Section’s CEO talk about using AI to stress-test board presentations. He went home and signed up for Section that night.
That personal journey is worth understanding, because it's the foundation of everything Sidearm did organizationally. George didn't mandate AI adoption from a distance. He was already deep in it himself. When he started asking his organization to take AI seriously, he wasn't asking them to do something he hadn't already done.
“From the beginning, George had a very clear vision for AI and how it impacts our industry,” said Elizabeth Pietrzak, VP of Operations at Sidearm. “Because of his understanding and excitement, we saw that it was more than just a homework assignment.”
Here are five lessons you can take from Sidearm’s AI journey, whether you’re just starting out or trying to un-stall a broken program.
1. Show people what’s in it for them
In January kicking off the year, George stood up at a company All Hands and said AI proficiency was now part of every personnel review.
His framing was direct: 90 days from now, it's hard to imagine anyone going on a job interview and not being asked about AI proficiency – so it’s in your best interest to embrace it now.
“I told them, this is going to become as table stakes as Excel skills for a finance person,” George said.
That combination – formal accountability through reviews, personal stakes through career framing – landed differently than a company initiative typically does.
The lesson: Make AI use an expectation, but help the “mandate” land by showing people how it will benefit them, not just the company.
2. Frame AI as a company differentiator and imperative
Sidearm works with premier college sports programs across the country. Every time they visit a school, they get asked the same question: “How are you thinking about AI?”
George’s answer is now unambiguous: every single person on our staff is AI proficient. Not “we're investing in AI” or “we have an AI strategy.” That's a meaningful differentiator when partners want to know that the companies they work with are ahead of the curve.
This framing also makes Sidearm’s AI transformation a non-negotiable for employees. If they don’t all embrace AI, clients won’t embrace them.
The lesson: Your internal capability is part of your external value proposition. Make it clear to employees and clients that you’re implementing AI to provide better service – not just to check a box.
3. The CEO or president should be the first “head of AI”
George could have handed off AI transformation to a direct report and never logged into ChatGPT himself. Instead, he got in front of the company and used the AI presentation tool Gamma live, showing how quickly a rough set of ideas becomes a polished deck.
His head of business intelligence, Amy Johnson, Director of BI, took it even further. She connected Claude to Gamma and demonstrated the combined workflow to the team and has been a strong advocate and influencer across the org.
The effect was cumulative. When your president is demoing tools and your head of BI is connecting systems live, AI starts feeling like “how work gets done.”
The lesson: Get your CEO and leadership team fluent in AI first. Employees will notice (and grumble) if they can sense they’re being told to use AI when the executives don’t.
4. Insist on a baseline before taking volunteers
One of the most deliberate decisions Sidearm made was about sequencing. They wanted an AI committee – a group of their most engaged people to drive use case development, governance, and the push toward agentic AI. But they didn't launch it immediately.
The reason: George didn't want a committee of enthusiastic people who were all at different starting points, pulling in different directions. Before anyone got a seat at the table, they needed to meet a defined proficiency standard. Every committee member had to be an “AI expert” first, as defined by Section’s proficiency methodology.
This ensured the AI committee had a similar level of understanding and expertise. George didn’t want people who were theoretically interested in AI but hadn’t put in the work.
The lesson: Don't let enthusiasm substitute for capability. Get everyone to a real baseline first, then build on top of it.
5. Don’t stop with enthusiasm - put in the work.
First, the CEO has to be all-in on AI – then the real work starts. AI transformation requires a steady drumbeat of change management, reporting, and structure to drive the change – and that’s where many companies fail.
Elizabeth Pietrzak, Sidearm VP of Business Operations, drove the operational backbone of the Section rollout. She built accountability benchmarks, set up governance structure, selected Sidearm’s suite of tools (Claude, Gamma, and Perplexity), and led the AI committee roll out – among many other tasks.
“George set the direction, but making AI stick across an organization takes more than a mandate,” Elizabeth said. “We built it into how we operate – our meetings, our peer outlets, our dashboards, our performance conversations, our toolkits, and how we work. When AI is part of the cadence, it stops feeling optional.”
The big question
As Sidearm launches their AI committee, their mandate will be focused on a single question: How does a digital company stay ahead of AI in their workflows, deliverables, and value proposition?
As you roll out AI to your team, focus on a similar question. Remind employees that it all comes back to doing better, more interesting, more valuable work – then do the work to model that behavior as a leader.
