Build
Founded Madrid Communications and co-founded Saltbox, a Salesforce systems integrator—building the strategy, operating model, delivery methodology and leadership foundation from zero.
Operator · Transformer · Advisor
From startup build to billion-dollar transformation.
Jon Madrid has built companies from the ground up, led mid-market turnarounds, carried a $1 billion P&L and advised Global 100 enterprises on transformation and AI.
Across technology, digital and operations, he has converted complexity into revenue growth, margin improvement, operating leverage and enterprise value.
Chief Technology Officer·Chief Information Officer·Chief Digital Officer·Chief Transformation Officer·Chief Operating Officer
Operating across stages and scale
Operating range
One operating discipline. Every stage of scale.
Different stages demand different moves. The constant is disciplined execution: understand the economics, align the operating model and build the capabilities that make growth durable.
Scale
Led 400- to 500-person organizations, a $130M budget and a $150M transformation portfolio across Best Buy and Ascena’s seven brands and 5,000 locations.
Transform
Reshaped billion-dollar and mid-market businesses, including $30M+ in first-year revenue, 50% lower operating cost and an 84% reduction in claims-processing time.
Advise
At AWS and Salesforce, translated technology into executive action—contributing to $100M+ in client savings, $250M+ in incremental revenue and $125M+ in identified AI value.
Executive leadership
Transformational leadership across the full executive mandate.
The titles changed with the work. The through line is accountability for increasingly consequential business outcomes.
Build
Chief Technology Officer
Founded and led Madrid Communications, then brought a technology operator’s lens to enterprise cloud transformation at AWS—work that contributed to $100M+ in client savings and $250M+ in incremental revenue.
Scale
Chief Information Officer
At Ascena, led a 400+ person organization, $130M budget and $100M omnichannel transformation across seven brands and 5,000 locations, producing $10M in sustained annual savings.
Grow
Chief Digital Officer
At Lifetouch, built the digital function for a $1B+ consumer enterprise, increased e-commerce revenue 25% in three months, reduced operating expense 15% in six months and supported the Shutterfly acquisition.
Transform
Chief Transformation Officer
At Novus Media, converted transformation into operating performance: $30M+ in first-year revenue, 50% lower operating cost, 20%+ efficiency improvement and a nine-month ERP replacement.
Operate
Chief Operating Officer
Carried a $1B P&L at Novus across Operations, Sales, Finance, HR, Data, Strategy and IT; later, as interim COO of a $60M insurer, cut claims cycle time 84% and delivered $5M in annual savings.
Now
Field Chief Technology Officer & AI Advisory Executive
At Salesforce, advises Global 100 leaders on AI strategy, governed data and agentic workflows—identifying more than $125M in efficiencies and new-revenue potential.
Value creation
An operator’s view of enterprise value.
Jon has worked inside the full business—not adjacent to it. That creates a practical perspective on the levers that matter to management teams, boards and investors.
Revenue acceleration
New products, digital commerce, go-to-market capability and AI-enabled growth—with outcomes from $30M to $250M+.
Margin expansion
Structural cost reduction, operating leverage and process redesign—including 50% lower operating cost and $20M in annual savings.
Operating model
Decision rights, talent, governance and execution systems that professionalize a growing business without slowing it down.
Technology & AI
Cloud, data, cybersecurity and agentic AI translated into investment priorities, measurable economics and controlled execution.
Transformation governance
Portfolio discipline across complex programs, from a $100M omnichannel transformation to a $150M enterprise portfolio.
Transaction readiness
Digital value creation, scalable infrastructure and leadership alignment that strengthen diligence, integration and exit narratives.
Executive perspective
The agentic enterprise is an operating-model transformation.
AI becomes consequential only when it changes how work is organized, how decisions are made and how value is measured.
Value before volume
Govern AI as an investment portfolio tied to economic and operating outcomes.
Data before autonomy
Ground intelligence in governed context, secure access and observable decisions.
Accountability before scale
Redesign ownership, decision rights and human-agent workflows before deployment outruns control.
Where the experience matters most
At inflection points where the next move changes the trajectory.
Jon’s range is most valuable when a business must connect strategy to execution—building a leadership system, scaling what works, resetting performance or turning technology and AI into measurable value.
Executive leadershipBoard rolesPE operating partner rolesStrategic advisoryInvestment opportunitiesEnterprise AI transformationExecutive speaking
Selective inquiries
For consequential roles and serious conversations.
Jon is open to select executive, board and operating-partner roles, as well as advisory work, investment opportunities and speaking engagements.
jon@jonmadrid.com(320) 266-2630LinkedIn ↗Independent views and activities are personal and do not represent Jon’s current employer. Engagements are considered subject to applicable professional obligations.