Our Story
Pragmatico helps humans and great organizations adapt and thrive at work in the age of AI.
We're living through a fundamental shift in how work gets done.
Most companies have deployed AI. Few see the transformation results.
The difficult truth: Good people and good businesses will be left behind in an increasingly AI-native economy.
At Pragmatico, we exist to guide you through this shift.
We help organizations become AI-native.
The gap is widening.
But you don't have to cross it alone.
We'll help you and your team not just adapt, but thrive in this next era of work.
The Pragmatico team
Leadership Team
We are proven business leaders first, and AI technologists second.
Santi Jaramillo
Co-Founder, Co-CEO
Santi is a 3x-exited technology founder and CEO, most recently of Emplify (acquired by 15Five). He's led AI transformations across organizations from 50 to 1,000+ employees, driving measurable results like 95% active AI adoption at Audiochuck, the media company behind the Crime Junkie podcast.
Unlike consultants who theorize, Santi has navigated the operational realities of scaling a business. He's a daily power user of cutting-edge AI tools and brings the rare combination of business strategy, deep AI knowledge, and cultural change management experience to Pragmatico client engagements.
Unlike consultants who theorize, Santi has navigated the operational realities of scaling a business. He's a daily power user of cutting-edge AI tools and brings the rare combination of business strategy, deep AI knowledge, and cultural change management experience to Pragmatico client engagements.
Randy Stocklin
Co-Founder, Co-CEO
Randy brings deep operational expertise to Pragmatico. He previously co-founded and led One Click Ventures, a DTC eyewear company, from startup to acquisition by FGX/EssilorLuxottica. EssilorLuxottica is a global leader in eyewear, with a portfolio of renowned brands including Ray-Ban, Oakley, Foster Grant, Chanel, and Prada. He's also been an active investor and advisor in Zeal, 60+ venture funds, and early-stage companies.
Randy focuses on driving measurable client AI adoption outcomes and building the operational systems that enable sustainable AI transformation at scale.
Randy focuses on driving measurable client AI adoption outcomes and building the operational systems that enable sustainable AI transformation at scale.
Our Mission
We help humans and great organizations adapt and thrive at work in the age of AI.
Our Values
Core Values
Our Values
Core Values
Customer Value Obsession
If it doesn't create measurable value for customers, we don't do it.
At Pragmatico, we put ourselves in our customers' shoes to fully understand their needs before prescribing solutions, and we pride ourselves on being ridiculously easy to work with. We proactively lead and guide our customers on their journey, measuring our success by theirs and turning them into raving advocates. Every decision starts with one question: "How does this help our customer succeed?"
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Customer Value Obsession
If it doesn't create measurable value for customers, we don't do it.
At Pragmatico, we put ourselves in our customers' shoes to fully understand their needs before prescribing solutions, and we pride ourselves on being ridiculously easy to work with. We proactively lead and guide our customers on their journey, measuring our success by theirs and turning them into raving advocates. Every decision starts with one question: "How does this help our customer succeed?"
Intrinsic Excellence
We bring our own drive and hold ourselves and each other to exceptional standards.
You bring your own motivation engine; no one needs to push you forward. Your standard for your work is higher than anyone's standard for you, and we expect teammates to deliver at that same level. We give clear, direct, constructive feedback because excellence requires it. You're relentlessly resourceful and think three steps ahead, knowing that good enough is never good enough if better is possible. When you see something that needs doing, you do it. Before delivering anything, ask, "Would I be proud of this?" If not, it's not ready.
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Intrinsic Excellence
We bring our own drive and hold ourselves and each other to exceptional standards.
You bring your own motivation engine; no one needs to push you forward. Your standard for your work is higher than anyone's standard for you, and we expect teammates to deliver at that same level. We give clear, direct, constructive feedback because excellence requires it. You're relentlessly resourceful and think three steps ahead, knowing that good enough is never good enough if better is possible. When you see something that needs doing, you do it. Before delivering anything, ask, "Would I be proud of this?" If not, it's not ready.
Truth & Growth > Comfort
Seek truth relentlessly, grow through what's hard.
The best idea wins at Pragmatico, regardless of who said it. We believe feedback is a gift, both giving it and receiving it. We say what needs to be said, not what's easy to say. "That won't work, and here's why" is caring. Silence is not. We lean into challenges that stretch us beyond comfort because inner development directly impacts team performance. We disagree and commit once a decision is made, and we choose growth over ego every single time. When you feel uncomfortable in a conversation or situation, lean in rather than pull back. That discomfort is where growth lives.
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Truth & Growth > Comfort
Seek truth relentlessly, grow through what's hard.
The best idea wins at Pragmatico, regardless of who said it. We believe feedback is a gift, both giving it and receiving it. We say what needs to be said, not what's easy to say. "That won't work, and here's why" is caring. Silence is not. We lean into challenges that stretch us beyond comfort because inner development directly impacts team performance. We disagree and commit once a decision is made, and we choose growth over ego every single time. When you feel uncomfortable in a conversation or situation, lean in rather than pull back. That discomfort is where growth lives.
Get Speeding Tickets, Not Parking Tickets
Bias to action, speed to value, momentum over perfection.
Done today beats perfect next week. The cost of delay exceeds the cost of mistakes, so we move fast and fix fast. Speed is a competitive advantage where momentum compounds. It's better to ask forgiveness than permission; when in doubt, act. Iterative beats deliberative; we build, test, learn, and repeat. If you're not occasionally making mistakes from moving too fast, you're moving too slow. We'd rather overstep and course-correct than play it safe and fall behind.
Read more
Get Speeding Tickets, Not Parking Tickets
Bias to action, speed to value, momentum over perfection.
Done today beats perfect next week. The cost of delay exceeds the cost of mistakes, so we move fast and fix fast. Speed is a competitive advantage where momentum compounds. It's better to ask forgiveness than permission; when in doubt, act. Iterative beats deliberative; we build, test, learn, and repeat. If you're not occasionally making mistakes from moving too fast, you're moving too slow. We'd rather overstep and course-correct than play it safe and fall behind.
Humans First, AI Forward
We blend deep human relationships with AI-native operations.
We care deeply about people while moving fast with AI, and we understand that human judgment trumps AI suggestion; AI informs, humans decide. We're AI-native in how we work, and every team member is an AI power user. Technology amplifies humanity rather than replacing it. We build real relationships with clients and each other because transformation requires trust. We practice what we preach because our adoption proves our methodology. Build trust through presence, deliver speed through automation.
Read more
Humans First, AI Forward
We blend deep human relationships with AI-native operations.
We care deeply about people while moving fast with AI, and we understand that human judgment trumps AI suggestion; AI informs, humans decide. We're AI-native in how we work, and every team member is an AI power user. Technology amplifies humanity rather than replacing it. We build real relationships with clients and each other because transformation requires trust. We practice what we preach because our adoption proves our methodology. Build trust through presence, deliver speed through automation.
The Opportunity
The world is dividing into two types of organizations: those who treat AI as tools and those who treat AI as transformation.
The first group will struggle. The second group will thrive. And the window to choose is closing.
We make mid-market companies AI-native so they can win in the AI economy.