Santiago Jaramillo

Co-Founder, Co-CEO & AI Transformation Lead

Pragmatico

Jul 2024 - Current (2 years)

I lead cultural AI adoption for mid-market companies stuck in the gap between deployment and transformation - where 72% have rolled out AI tools but 80% see minimal returns. The core problem: Organizations treat AI like an IT rollout when it's actually a cultural transformation. Change management firms lack AI depth. AI consultants ignore cultural dynamics. Internal committees meet endlessly while adoption stalls. Our approach: We architect full cultural transformations using our proven 3-step system: Align & Architect: AI Manifesto and Policy that create psychological safety and clear vision before any training Activate Behaviors: Hands-on AI training combined with incentive structures and accountability - skills alone don't work; sk

Founder, Managing Director & AI Transformation Lead

Pragmatico

Jul 2024 - Current (2 years)

I lead cultural AI adoption for mid-market companies stuck in the gap between deployment and transformation - where 72% have rolled out AI tools but 80% see minimal returns. The core problem: Organizations treat AI like an IT rollout when it's actually a cultural transformation. Change management firms lack AI depth. AI consultants ignore cultural dynamics. Internal committees meet endlessly while adoption stalls. Our approach: We architect full cultural transformations using our proven 3-step system: Align & Architect: AI Manifesto and Policy that create psychological safety and clear vision before any training Activate Behaviors: Hands-on AI training combined with incentive structures and accountability - skills alone don't work; sk

Coach & Business Operating System Practice Lead

InsideOut Leadership

Mar 2023 - Dec 2025 (2 years 10 months)

I guide high-performing founders, CEOs, and executives through the critical transitions that define scaling businesses—helping them evolve as leaders without burning out or hitting growth plateaus. As a 3x founder who's built and exited companies across diverse industries, I bring 40,000+ hours of real-world CEO experience to my coaching practice. I don't just teach leadership concepts—I share battle-tested strategies from someone who's navigated these exact challenges firsthand. My approach combines three core pillars: - Executive Coaching — Evolving leadership capabilities before you hit the wall - Business Operating Systems — Building scalable systems that carry companies beyond founder-led stages - Practical AI Implementation — Stayin

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Executive Coach @ WithSanti.com

WithSanticom

Jan 2023 - Current (3 years 6 months)

I guide high-performing founders, CEOs, and executives through the critical transitions that define scaling businesses—helping them evolve as leaders without burning out or hitting growth plateaus. As a 3x founder who's built and exited companies across diverse industries, I bring 40,000+ hours of real-world CEO experience to my coaching practice. I don't just teach leadership concepts—I share battle-tested strategies from someone who's navigated these exact challenges firsthand. My approach combines three core pillars: - Executive Coaching — Evolving leadership capabilities before you hit the wall - Business Operating Systems — Building scalable systems that carry companies beyond founder-led stages - Practical AI Implementation — Stayin

Sabbatical

Selfemployed

May 2022 - Feb 2023 (10 months)

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Sabbatical

May 2022 - Feb 2023 (10 months)

15Five Senior Executive & Member of the Board

FIVE

Apr 2021 - May 2022 (1 year 2 months)

15Five is a human-centered performance management platform that creates effective managers, highly engaged employees, and top-performing organizations. From engagement surveys and 1-on-1 tools to performance reviews and OKRs, 15Five is the most complete solution that combines software, education, and community to develop successful managers and unlock peak employee performance. Built using the Positive Product Design™ method, 15Five is the only platform that offers software aligned to the latest positive psychology research. Through it’s HR Superstars community and podcast, 15Five aims to empower every leader to create highly engaged, high-performing organizations by helping people become their best selves.

CEO & Co-Founder (Exited to 15Five)

Emplify

Sep 2015 - Apr 2021 (5 years 8 months)

Emplify is on a mission to help organizations unlock human potential so employees can do the best work of their lives. While US companies spend a staggering $720 million annually on employee engagement, measuring the return on this investment is often derived from outdated annual surveys or ad-hoc polls. Emplify’s unique agile engagement platform leverages both quantitative and qualitative employee feedback through hassle-free survey administration and analysis to provide visibility across the entire organization to leaders. Rooted in the belief that yearly surveys alone are no longer effective to create highly engaged cultures, Emplify’s agile measurement framework combines surveys with quarterly check-ins and pulse polling to uncover the

CEO & Founder (Exited to PushPay + Simpleview)

Bluebridge Digital

Jun 2011 - Feb 2017 (5 years 9 months)

Bluebridge helps organizations communicate and engage with their internal audience (employees) and external audiences (customers, visitors, members, etc) through a mobile app engagement platform. Corporations use the Bluebridge Mobile Engagement Platform to communicate internally with their employees and many, like Conventions & Visitors Bureaus (communicate with visitors) and Churches (communicate with their congregations), leverage the Bluebridge mobile app engagement platform to communicate with their external audiences. With interactive app content features and world-class, highly personalized push notification messaging capabilities, the Bluebridge platform empowers organizations to grow their organizations by engaging their audience

Asia-Pacific Partnerships - Sydney, Australia

ExactTarget

Jan 2011 - May 2011 (5 months)

Worked with Partners Manager to develop and nurture ExactTarget's relationships with key partners in Asia-Pacific such as: Microsoft, Adobe Omniture, Webtrends, Salesforce.com, BazaarVoice, and others. As part of the partnership team, met over 150% of the sales target for Q2 2011 in channel revenue, trained sales staff on on how to leverage partners to close more business, and coordinated ExactTarget's presence at several partner events: Webtrends Engage 2011 (Sydney) and Dreamforce 2011 (Sydney).

Competitive Intelligence

ExactTarget

May 2010 - Jun 2011 (1 year 2 months)

Lead out ExactTarget's competitive intelligence programs and strategy. Publish the weekly CI Newsletter as well as support the sales organization in competitive situations.

Product Marketing 'Slingshot'

ExactTarget

Mar 2010 - Aug 2010 (6 months)

Specialized in competitive intelligence in the Product Marketing. Drove the creation of the Competitive Insight Newsletters, with all of ExactTarget's worldwide employees as the audience. The newsletter included analysis and positioning on competitor's actions in the industry. Was brought in by the corporate sales team to aid in engaging a prospect in an international opportunity. Built rapport and overcame objections to close a significant international deal in Spanish.

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Founder

US Music Camps

Jul 2009 - Jul 2011 (2 years 1 month)

Founded and directed entrepreneurial venture; designed and implemented marketing plan including website with e-commerce integration, direct mail, email marketing, and print media advertising campaigns. Hired and led staff of 20 and served over 120 customers. Developed plan to expand to three locations in 2009 and executed the plan in the summer of 2010 successfully to expand into two states.

Santiago Jaramillo

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