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About Calafai

Senior strategy work, built by someone who did it by hand.

Calafai is an AI strategy platform. You describe a business challenge. It researches it from multiple angles, checks the quality of its own work, verifies every source, and challenges the conclusions before you see a deliverable.

You steer it. You add context, challenge the direction, bring your judgment. What comes back is a professional working document you iterate on: present it to your team, share it with your board, or build your next quarter on it. Your expertise drives the outcome. Calafai handles the analytical heavy lifting. The decisions stay yours.

Most AI answers questions. Your problem is a project.

Most AI tools are built for questions. Strategy work isn't a question. It's a project, where competitive analysis feeds financial projections that shape a go-to-market plan. Change one assumption and three deliverables shift.

Calafai is built for that kind of work. Analysis examined from multiple angles. Sources verified and graded by reliability. Conclusions challenged before they reach you. Every deliverable arrives with honest quality assessments so you know where to trust it and where to apply your own judgment.

It doesn't think for you. It helps you think.

Strategy kept getting made above the people who knew better.

Calafai grew out of a specific frustration: the people inside a company who know how the business actually runs today, the real bottlenecks, the workarounds, the nitty-gritty that never makes it into the corporate deck, are rarely given the budget or the time for top-tier strategy work. Strategy gets made above them and handed down, and nothing flows back. Top-down is not the problem: direction should flow down. But ground truth has to flow up to inform the strategy, or the people at the top are guessing and hoping. The people who hold that ground truth are exactly the ones to equip with strategy tools.

The founder saw the cost of that firsthand. A C-suite strategy, built on the assumption that a global supply chain worked the way the diagram said it did, would have brought that supply chain to a screeching halt and cost the company billions. It did not, only because someone at the ground level did the real diligence, someone who knew how the strategy, the execution, and the technology actually fit together. The big firms rarely see that layer. The people doing the work live in it, but rarely have the time, the tools, or the training to scale what they know to the scope of the whole company.

Calafai began as the founder's own tool, built from fifteen years of doing the work by hand: creative agencies, the U.S. intelligence community, and a decade at Nike. It combined the frameworks of an MBA, a technologist's grasp of how systems really behave, and an intelligence analyst's discipline with evidence, so one person could deliver more value in less time. Now it exists so everyone can.

The design philosophy comes from a principle called ground truth: don't read the process doc and assume that's how the work happens. Go observe. Understand the reality on the ground. Then build from there. That habit runs through everything Calafai does.

That matters more than ever. In the world of AI, everyone is being asked to deliver more work, at higher quality, with the same time and resources they had before. Calafai exists so the people closest to the real work can actually do that.

Calafai: named for a promise to return.

Cah-lah-fye

In Patagonia there's a thorny bush called the calafate that produces a small dark berry. The Tehuelche legend says that anyone who eats the fruit is destined to return.

The name has roots in a few places. Cala is what they call coves and sheltered harbors across the Mediterranean. Fai, in Italian, means you make. In Mandarin, fēi means to fly. A sheltered harbor where you build something that takes flight. And that you're destined to come back to.

Changing strategy takes seventeen months. It should take two.

Picture a company that decides to change its strategy and actually changes, at global scale, in less than two months. Today that story takes closer to seventeen: the executive team spends months translating the announcement, every function derives its own version, plans cascade level by level, and activation drags while people work out who owns what. By the time the strategy reaches the people doing the work, the board is already asking why nothing has moved.

Calafai is being built for the other version of that company. The strategy is announced once, and every level, from the executive team to the individual contributor, starts from an aligned draft of its own part in it. People steer, push back, and contribute what they actually know. Ground truth flows up while direction flows down, and the impact of a change propagates in both directions. The plan inherits from below, directs from the top, and puts the people the company already employs to work instead of routing around them.

One comprehensive strategy, alive at every level of the organization, fast enough to turn a global company on a dime.

Today, the sharpest version of that is the 4-workshop strategic engagement: a defined problem taken from a rough brief to a decision you can act on, with Chris in the work, not on a call about it. Deliberately selective, built for people who expect top-tier rigor at a fraction of the time and cost.

See how the 4-workshop engagement works

A designer with an MBA who spent a decade on enterprise and consumer digital products at Nike, and before that, built analytical software for the U.S. defense and intelligence community. Calafai is where those three trades meet.

Seven of those Nike years were at World Headquarters in Portland, three in Europe. Before Nike, creative campaigns for Discovery Communications across seven television networks.

At Nike he led service and experience design across European operations, directed design for thirteen AI and analytics product squads, and built design disciplines from zero across supply chain, demand planning, and inventory operations. His work sits at the intersection of design, technology, and business strategy. He designs the experience, writes the code, and builds the business case. Most organizations need three people for that.

He spent seven months off-grid in Patagonia and learned the hard way that the best plans survive about twenty minutes of actual weather. In the mountains and in the boardroom.

MBA, UNC Kenan-Flagler · BA, Lehigh University (Graphic Design & Political Science) · Aspen Institute Executive Leadership Seminar · Maine Media Workshops, Photography Residency · NOLS Patagonia

Not ready to bring a problem yet? Read a real engagement end to end, or start free with 200 credits.

Bring Chris a real problem.

Not a demo request. Send the actual question you're wrestling with: a market-entry call, a strategy that needs pressure-testing, a partnership you're weighing.

Read by Chris himself

Replies personally when it's a fit. No sales sequence, no list.

Goes straight to Chris.