DekaBridge isn't a traditional consulting firm that happens to use AI tools. We're an AI-native organization that merges agentic automation with expert judgment to deliver transformation outcomes for product leaders.
Founder & CEO
Skyler is a serial AI entrepreneur and one of the leading voices on how artificial intelligence reshapes human decision-making in organizations. His career sits at the intersection of cognitive science, AI systems, and executive leadership — a combination that makes him uniquely qualified to help product organizations separate judgment from intelligence.
With a PhD in Cognitive Psychology specializing in human decision-making, Skyler spent years studying how people actually exercise judgment. That research foundation is the backbone of DekaBridge's framework: understanding which work requires human experience and taste, and which can be systematically delegated to AI.
Before founding DekaBridge, Skyler spent over a decade as Chief Behavioral Science Officer at Cogito, where he led AI strategy and product management — deploying emotionally intelligent AI at the world's largest consumer brands, healthcare providers, and telecom companies. He's guided Fortune 500 organizations to bring AI into their business operations and product roadmaps, improving outcomes for their businesses, customers, and employees. He also co-founded CompanionMX, leading R&D and product creation of a clinically validated digital health application. Skyler currently serves on the faculty at Harvard School of Public Health, guiding executives on AI strategy and risks. He has authored eight patents and over a dozen publications at the intersection of machine learning, health, and communication.
Skyler holds a BA in computer science from Colby College, PhDs in psychology and cognitive science from Indiana University, and completed his post-doctoral work in computational social science at the Institute for Quantitative Social Science at Harvard University.
Our own org runs on the same judgment-intelligence bifurcation we help clients build. Agentic systems handle the intelligence work; human experts focus on judgment. We have firsthand credibility because we've lived the transformation.
We work across the SaaS landscape with product leaders all facing the same inflection point. Every engagement deepens our pattern library and improves our agent templates — a compounding advantage that benefits every client.
Clients buy transformation outcomes, not billable hours. As AI models improve, our delivery gets better and more efficient — which means the value we provide compounds over time, not commoditizes.
Every conversation with product leaders reveals the same themes — and the same urgency.
Engineering's future is clear: agentic code generation, Claude Code, Copilot. But there's no equivalent clarity for what an AI-native product management organization looks like. That gap is where we work.
For the first time, engineering leaders are talking about 10x productivity. If product can't keep pace, product becomes the constraint in the R&D pipeline. This is forcing product leaders to act.
The real transformation isn't making PMs faster with AI tools. It's systematically separating intelligence work from judgment work — then redesigning roles, processes, and tools around that split. No one has done this for product management before.
The industry is shifting from selling tools to professionals (copilots) to delivering outcomes directly to organizations (autopilots). DekaBridge is positioned on the autopilot side: we deliver transformation results, not software licenses.
Every engagement starts with a conversation. No pitch decks, no pressure — just a candid discussion about where your organization is and where it could be.
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