Santiago Jaramillo

Co-Founder

United States16 yrs 9 mos experience
Most Likely To SwitchHighly Stable

Key Highlights

  • Founder of an AI cultural transformation company.
  • 3x exited founder with extensive executive coaching experience.
  • Amazon best-selling author and recognized business leader.
Stackforce AI infers this person is a SaaS executive specializing in AI transformation and leadership development.

Contact

Skills

Core Skills

Ai CoachingLeadership DevelopmentCultural Change ManagementExecutive CoachingExecutive Leadership

Other Skills

Strategic Planning FacilitationBusiness InnovationTrainingCoaching360 Performance Review FacilitationBoard of DirectorsPublic SpeakingUser InterfaceiOS DesignNew Business DevelopmentSales PresentationsStrategic PartnershipsMobile TechnologyMobile DesignEntrepreneurship

About

I’m the founder and co-CEO of Pragmatico, an AI cultural transformation company. I serve as a Fractional Chief AI Officer for organizations like Prime Hospitality Group and Audiochuck (creator of Crime Junkie), where we grew AI adoption from 12% intermittent use to 95% skilled, active usage. Building world-class teams that solve real business problems is what gets me out of bed in the morning. I'm also a 3x-exited founder and executive coach. I’ve spent the last decade helping hundreds of leaders transform their cultures through data-driven insights and coaching. I co-founded Emplify, an employee engagement measurement company, which was acquired by 15Five in 2021. I started my executive coaching practice shortly thereafter. On the personal side, I’m a proud Colombian immigrant, drummer, hot yoga enthusiast, and world traveler (40 countries and counting). Here on LinkedIn, I write about: - The human aspects of AI transformation - How to lead well without losing yourself - Lessons learned from my own entrepreneurial and leadership journey Other awards and accomplishments include: - Amazon best-selling author of “Agile Engagement” - Indiana Latino Businessman of the Year - Indianapolis Business Journal 40 Under 40 - Inc. Magazine's 30 Under 30 Whitehouse.gov "Champion of Change"

Experience

16 yrs 9 mos
Total Experience
2 yrs 8 mos
Average Tenure
3 yrs 3 mos
Current Experience

Pragmatico

Co-Founder, Co-CEO & AI Transformation Lead

Jul 2024Present · 1 yr 9 mos · Nomadic/Worldwide · Remote

  • I lead cultural AI adoption for mid-market companies stuck between tool deployment and transformation. Only 5% of organizations are seeing real returns on AI, despite 88% reporting AI investments (sources: BCG; McKinsey).
  • At Pragmatico, we believe that leadership’s biggest AI challenge isn't technical, but cultural. That's why we operate at the intersection of cultural change management, AI expertise, and practical business execution.
  • Pragmatico’s proven AI Cultural Adoption System, trusted by companies like Audiochuck, Indiana Farmers Insurance, and Prime Hospitality Group, guides companies through every stage of AI adoption and transformation. We move teams from intermittent or hidden usage to 90%+ active adoption with measurable productivity and ROI.
  • Our 3-step approach:
  • 1. Align & Architect: Train leadership on AI, build an AI Manifesto and Policy that create psychological safety and clear vision, and create a winning AI cultural change management plan with incentives, recognition programs, peer sharing and ongoing AI training, coaching and support
  • 2. Activate Behaviors: activate AI Manifesto and policy team-wide, provide hands-on AI training combined with application homework, incentive structures, recognition programs, and org-wide accountability and support
  • 3. Operationalize & Sustain: Build adoption and ROI dashboards, ongoing AI education and roadmapping programs, and HR integration that make AI proficiency permanent
  • Beyond AI cultural transformation, Pragmatico offers AI Automation and Agent Development for organizations ready to deploy solutions within an adoption-ready culture.
AI CoachingLeadership DevelopmentStrategic Planning FacilitationExecutive LeadershipBusiness Innovation

Inside-out leadership

Coach & Business Operating System Practice Lead

Mar 2023Dec 2025 · 2 yrs 9 mos · Remote

  • 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 — Staying competitive and future-ready without falling behind
  • What differentiates my work is the integration of personal leadership development with operational excellence and modern technology adoption. I help clients avoid the predictable roadblocks that stall growth by providing the foresight that comes from having walked this path before.
  • The result? Leaders who grow faster than their business demands, operate with clarity and confidence, and scale beyond themselves while maintaining their sense of purpose and well-being.
Executive CoachingLeadership DevelopmentStrategic Planning Facilitation360 Performance Review Facilitation

Withsanti.com

Executive Coach @ WithSanti.com

Jan 2023Present · 3 yrs 3 mos · Remote

  • 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 — Staying competitive and future-ready without falling behind
  • What differentiates my work is the integration of personal leadership development with operational excellence and modern technology adoption. I help clients avoid the predictable roadblocks that stall growth by providing the foresight that comes from having walked this path before.
  • The result? Leaders who grow faster than their business demands, operate with clarity and confidence, and scale beyond themselves while maintaining their sense of purpose and well-being.
Executive CoachingAI CoachingStrategic Planning FacilitationExecutive Leadership

Self-employed

Sabbatical

May 2022Feb 2023 · 9 mos

Executive CoachingExecutive LeadershipBoard of DirectorsPublic SpeakingBusiness Innovation

15five

15Five Senior Executive & Member of the Board

Apr 2021May 2022 · 1 yr 1 mo

  • 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.

Emplify - employee engagement

CEO & Co-Founder (Exited to 15Five)

Sep 2015Apr 2021 · 5 yrs 7 mos · Fishers, Indiana

  • 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 core issues behind symptoms like high turnover, low productivity, and poor innovation, enabling leaders to make data-driven decisions that bridge people and profit. Learn more at emplify.com.

Bluebridge

CEO & Founder (Exited to PushPay + Simpleview)

Jun 2011Feb 2017 · 5 yrs 8 mos · Indianapolis, Indiana Area

  • 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 through branded, compelling, and easy-to-use native mobile apps. With over 500 mobile apps published in various app stores and serving hundreds of customers around the world, Bluebridge is headquartered in Indianapolis, IN where the team of over 30 passionately builds the future of mobile communication and engagement. Learn more at gobluebridge.com.

Exacttarget

3 roles

Asia-Pacific Partnerships - Sydney, Australia

Jan 2011May 2011 · 4 mos

  • 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

May 2010Jun 2011 · 1 yr 1 mo

  • 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'

Mar 2010Aug 2010 · 5 mos

  • 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.

U.s. music camps

Founder

Jul 2009Jul 2011 · 2 yrs · Indianapolis, Indiana - Anderson, Indiana - Tamarac, Florida

  • 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.

Education

Indiana Wesleyan University

Bachelor of Science; Bachelor of Science — Business Administration; Marketing

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