Cliff Simon, CRO of Carabiner Group, a part of SBI, represented SBI at ChiliPalooza, a dynamic, workshop-driven conference hosted by Chili Piper. The event gathered some of the sharpest minds in B2B revenue and go-to-market leadership.
A common theme was embedded into every conversation: AI is reshaping the game, and companies are moving fast to figure out how to integrate it into marketing, sales, and customer experience workflows.
This idea was central to our findings in how CEOs are thinking about AI in 2025.
Real Conversations Around AI
From content creation to brand building to sales coaching, discussions on AI implementation were everywhere. What stood out wasn’t the tools, but the urgency to find what works and lack of differentiation in the market. Brands are building lookalike products with 60-70% of the same features, and fast. Defensibility is shrinking.
That begs the question: How do you stand out?
Two key takeaways to drive differentiation emerged: building a trusted brand and curating an in-person presence. In a world flooded with AI-generated content that all starts to sound the same, a distinct brand identity and the way you show up in the real world will set you apart.
SEO is Out, AI Summaries Are In
Traditional SEO efforts are not delivering the same level of organic leads that they used to. With paid ads dominating results and AI-generated summaries taking over the top of the page, even the number one organic search result gets buried.
The new challenges companies face is figuring out how to show up in AI summaries. It comes down to authority and originality. AI tools are favoring content that is authoritative, specific, and backed by real data. One unexpected source of information stood out: Reddit. Not branded posts or corporate articles, but rather authentic user discussions. Alongside sources like Wikipedia, Reddit threads are being surfaced by AI engines as trusted areas of credibility and relevance.
Brands that want to stay visible need to focus on delivering content with real substance and authenticity.
AI for Coaching
One takeaway came from an impactful conversation with Kevin Dorsey, Founder and CEO of Sales Leadership Accelerator, on how AI can drive real skill development. Instead of relying on AI tools to create emails or automate outreach, Kevin is focused on delivering value through upskilling frontline managers and sales reps.
The most compelling concept was how AI can be used to reinforce skills through deliberate practice. His teams dedicate 15-20 minutes a day to drill down on one specific skill. The goal is to master the building blocks of effective selling through targeted repetition and real-time feedback.
There's an immediate parallel to pro sports. Just like a professional soccer team needs roughly 200 sessions to fully internalize skills within a new system, reps need the same reinforcement to adopt and execute new skills and workflows.
No Keynotes
Chilipalooza’s format was refreshing. No keynotes, no panels, no fluff. The conference was entirely made up of hands-on workshops with expert-led discussions.
Everyone in the room was an expert. This created a space for real dialogue, real problem solving, and real solutions.
Looking forward to next year!
