About IterateOn

The Truth in AI—From People Who’ve Tried It

IterateOn is a curated membership experience for enterprise leaders actively experimenting with Generative AI and automation. It’s built around peer sharing, orthogonal thinking, and the belief that cross-industry collaboration leads to breakthrough innovation.

The idea for IterateOn was sparked by a direct request from Ekta Chopra, e.l.f. Cosmetics Chief Digital Officer, whose team came to Iterate.ai with a challenge:

Peer-Tested AI. No Booths. No Hype.

Together, we co-developed this concept to create a high-trust environment where enterprise leaders could learn from one another—not just from the $100 billion to $2 trillion platforms that dominate industry conferences, sales cycles, and marketing budgets. Industry events are often filled with massive booths, polished keynotes, and pay-to-play stage time—giving Big Tech and other large vendors the loudest voices, whether or not their solutions deliver the best value.

KPI-driven leaders at companies like e.l.f. aren’t chasing the flashiest booths or the biggest brands—they’re chasing the truth. They want to know what’s working, what’s not, and how to move fast without blowing the budget. Speed-to-market, flexibility, and cost-effective execution aren’t just buzzwords—they’re priorities. These leaders rely on real-world experimentation and remain especially open to insights from adjacent industries, where the boldest breakthroughs so often begin.

The most innovative executives understand that innovation rarely comes from the center. Airbnb wasn’t created by hoteliers. Uber didn’t come from a taxi company. SpaceX wasn’t born inside Boeing or NASA. And Amazon wasn’t built by a traditional retailer. Orthogonal thinkers launched Netflix, Stripe, Block (Square), Tesla, Zoom, Slack, Palantir, and countless others. Disruption often comes from the edge—from outsiders who see the problem differently. Every company can benefit from open minds and orthogonal thinking.

IterateOn was built to meet that need: a space where AI conversations are honest, peer-driven, and grounded in practical outcomes.

Built Across the Generative AI Stack

IterateOn brings together leaders from every layer of the Generative AI technology stack. Because breakthrough innovation doesn’t happen in silos—it happens when infrastructure meets imagination, when models meet markets, and when unexpected collaborations unlock new value.

You’ll find three core layers at the heart of today’s GenAI ecosystem:

Application Layer

This is where AI becomes real—visible and usable. It’s where AI is transformative inside organizations.

Trailblazers are pushing boundaries here, using AI to reshape everything from customer experience to internal operations.

To foster rich discussions and knowledge sharing, we will include numerous brands operating in this layer, such as e.l.f. Cosmetics—which achieved over $1 billion in net sales with a 77% growth in fiscal 2024—and MUFG, the largest bank in Asia outside of China, with $2.6 trillion in assets. Their participation will provide valuable insights into how AI applications are reshaping customer experiences and internal operations across diverse industries.

Model Layer

Here live the minds behind the machines—foundation models, fine-tuning engines, and large language systems.

This is the domain of players like OpenAI and InflectionAI, building the intelligence that powers today’s most compelling AI applications.

Infrastructure Layer

The infrastructure landscape is more dynamic than ever, with major tech companies making substantial investments to bolster their AI capabilities:

• Amazon plans to invest over $100 billion in 2025, with the majority allocated to enhancing AI capabilities within its cloud division, AWS. ​
• Microsoft intends to invest approximately $80 billion in fiscal year 2025 to develop AI-enabled data centers globally. Additionally, it has entered a 20-year agreement to purchase power from the Three Mile Island nuclear plant, aiming to support the energy demands of its expanding AI data centers.
• Meta Platforms plans to invest $60 to $65 billion in CapEx this year, focusing on data centers and AI development teams to advance its AI ambitions. ​

Some companies straddle multiple layers of the AI stack. For instance, DeepSeek and Iterate.ai span all three layers—Infrastructure, Model, and Application—building vertically integrated capabilities that connect infrastructure, intelligence, and interface.

But here’s the truth:

No single layer wins alone. And no company wins alone—not NVIDIA, not Microsoft, not OpenAI, not Meta. The GenAI ecosystem is deeply intertwined.truth:

• The Application Layer depends on trustworthy, well-trained Models.
• The Model Layer relies on a powerful, scalable Infrastructure Layer.

And none of it matters without real-world experimentation and, even more importantly, deployments (with continuously monitored metrics) to close the loop.

That’s why IterateOn was designed for multi-dimensional, cross-layer, cross-industry collaboration. We want to learn from each other.

The most valuable conversations often happen when a CTO from a beauty brand hears from a model researcher—or when a hardware exec sees how their chips are powering an unexpected retail breakthrough either on the cloud or a low-power edge device.

What’s Included in IterateOn

Two In-Person Symposium Events per Year

Each AI Symposium is a high-trust, invite-only gathering designed for honest discussion and shared exploration. These events are structured to unlock insights and accelerate implementation by exposing Members to real-world examples and fresh mental models.

Symposiums include:

• Trend Talks by specialists and experts, designed to open participants’ minds
• AI Success Presentations by Members
• AI Challenge Presentations by Members
• Challenge Solving Sessions in small, non-competitive peer groups
• Networking with AI professionals across industries and across the GenAI tech stack—to encourage orthogonal thinking and surprising idea transfers

Ten 25-Minute Webinars per Year

These fast-moving virtual sessions spotlight timely topics in Agentic AI, Private AI, deployment strategy, and use case design. Each webinar runs 25 minutes, including 5 minutes of Q&A. Think: compact, smart, and immediately applicable.

Special Interest Groups (SIGs)

SIGs are small, action-oriented communities that form around shared goals, technologies, industries, or use cases. These groups are built to move fast—exchanging insights, troubleshooting challenges, and helping Members implement what matters.

SIGs are seeded through conversations and connections at each Symposium. IterateOn organizers help identify shared interests and catalyze these groups, giving Members a launchpad to deepen collaboration and speed up results.

Unlike traditional councils—often formal, fixed, and governance-driven—SIGs are built for momentum. They’re dynamic, curiosity-fueled, and focused on learning through doing. Each group sets its own pace—some meet monthly, others quarterly—but all share a common goal: accelerate progress through peer-driven experimentation and exchange.

Hackathons

Note: We are exploring the integration of hackathons into the IterateOn experience. This initiative is under consideration and not yet part of the official Charter, as we aim to design these events thoughtfully to maximize value for our Members.

Envisioned as dynamic, collaborative events, these hackathons would unite diverse AI enthusiasts and professionals to tackle real-world challenges through creative problem-solving and rapid prototyping. By fostering cross-industry collaboration and innovative thinking, participants would have hands-on opportunities to apply AI technologies in novel ways.

Potential collaborators for these events include groups such as Cerebral Valley and/or Sundai Club. Engaging with such communities can infuse our hackathons with fresh perspectives and cutting-edge ideas, aligning with IterateOn's commitment to fostering innovation through diverse and collaborative efforts.

Let's Iterate!

Note: Iterate.ai reserves the right to adjust the cadence, format, or number of in-person and online gatherings based on Member feedback and evolving needs. We aim to keep IterateOn practical, high-value, and responsive to what matters most.