Michael Caraballo | Executive + Builder

I turn complex organizations into systems people can trust.

I’m a technology executive, enterprise architect, and hands-on product builder. For more than 20 years, I’ve connected finance, operations, data, AI, and engineering, staying close enough to the work to make the strategy real.

Explore the work
20+

years leading and building technology

50+

agency brands aligned on enterprise platforms

DaysMinutes

employee provisioning through automation

01

native commercial product shipped to the Mac App Store

01 / Point of view

Strategy matters most when it survives implementation.

I’ve spent my career in the space between an executive decision and the system that has to carry it. This involves discussing margin, risk, and operating models with leadership, and then collaborating with engineers on the schema, interface, integration, or deployment that makes the decision executable.

My best work makes complexity disappear without pretending it was simple. It gives people a clearer decision, a safer process, or a tool they genuinely want to use.

02 / Selected work

Leadership made visible.

Four stories that show how I move between product, enterprise architecture, operational design, and executive decision support.

01 / Product Ownership

TayzoPrompter

Creating a product people can trust.

Live on the Mac App Store

Building TayzoPrompter taught me that software development is only a small part of creating a product people can trust.

There were days when I knew exactly how to solve a technical problem. There were just as many days when I didn't.

Sometimes the challenge wasn't technical at all. It was deciding what the experience should feel like. What a customer would reasonably expect. Whether a feature actually deserved to exist. How to make something powerful feel effortless.

Those aren't problems an IDE solves for you.

Over the past year I found myself solving problems I never imagined when I first started writing code.

How should a subscription be priced so it creates a sustainable business without making customers feel trapped? How long should a free trial be? Should there even be a perpetual license? How do you explain a feature without overwhelming someone who has never used a teleprompter before?

How do you earn trust before asking for microphone, camera, speech recognition, or screen recording permissions? How do you design onboarding that teaches without getting in the way?

Those questions never produce compiler errors. But they determine whether a product succeeds.

Working with Apple's App Review process was another lesson in product development.

Many people think shipping an app simply means uploading a build. It doesn't. Apple examines every interaction through the eyes of a customer. Every permission request. Every onboarding screen. Every subscription explanation. Every screenshot. Every button.

Sometimes their feedback meant redesigning interfaces. Sometimes it meant strengthening the application's architecture. Sometimes it meant improving documentation. Sometimes it meant rethinking how I introduced features to new users.

Looking back, I'm grateful for that scrutiny because it forced me to create a better product.

One thing I learned is that every product is really a collection of thousands of tiny decisions.

Most people will never notice them individually. But they absolutely notice when they're missing.

A button that's slightly confusing. A permission request shown at the wrong moment. An onboarding screen that asks for trust before it's earned. A recording that fails because an audio device disappeared. A subscription screen that feels manipulative. A dialog that doesn't quite feel like Apple.

Those details became my responsibility. Eventually I found myself enjoying those decisions just as much as writing the code.

Building TayzoPrompter also reminded me that leadership doesn't stop at engineering.

I had to think like a designer. Like a product manager. Like a marketer. Like a technical writer. Like customer support. Like legal counsel. Like finance. Like operations.

I had to understand infrastructure costs, subscription economics, privacy, terms of use, accessibility, App Store metadata, marketing videos, brand identity, documentation, long-term maintenance, and customer expectations.

None of those responsibilities existed in isolation. Every decision affected the others.

AI became an incredible tool throughout this journey.

It accelerated implementation. It challenged my thinking. It helped me explore alternatives faster than ever before.

But AI never decided what the product should become. It never chose which feature deserved to exist. It never determined whether something felt intuitive. It never knew when simplicity was more valuable than capability.

Those decisions still required experience, judgment, empathy, and ownership.

AI helped build the product. Leadership shaped it.

I don't think TayzoPrompter represents an application.

It represents persistence. Hundreds of design decisions. Thousands of engineering decisions. Countless tradeoffs. Many conversations with Apple's reviewers. Repeated iterations. And a willingness to keep refining until it genuinely felt ready.

That's the kind of work I enjoy most.

Not simply writing software.
Creating products people can trust.

02

Enterprise transformation

Helping 50+ brands operate like one business

Growth and acquisition had left financial, workforce, expense, and job-management systems fragmented across agency brands. Every cutover carried real close, billing, access, and continuity risk.

I led cross-functional architecture and migration work that standardized the operating backbone while respecting different legal entities, controls, and business models. The program established repeatable integration patterns and completed high-stakes transitions with zero unplanned downtime.

Scale 50+ brands · global multi-entity environment
03

Consulting · Decision intelligence

Giving leaders one governed view of the business

A multi-company organization was making profitability decisions across disconnected actuals, budgets, rolling forecasts, and client trackers. The problem was not another dashboard; it was a trustworthy data model.

Through Carabuilt Consulting, I designed a pragmatic Microsoft 365 and Power BI architecture that normalized finance-controlled inputs, established shared dimensions, handled monthly currency conversion, and applied role-based access. Weighted margin logic kept totals financially valid; drill-through connected an executive signal to the company, client, month, category, and GL evidence behind it.

The result gave leadership an operating conversation: where revenue and margin were moving, which clients explained the gap, how the latest forecast differed from plan, and where intervention would create the most value.

Scope 4 operating companies · actuals, budget & rolling forecasts
Interactive demonstration created from real production architecture using sanitized sample data.
04

Behavior-aware systems

Solving the behavior instead of sending another reminder

Late time entry was treated as a communications problem, even though reminders kept producing the same result. I reframed it as a systems-design problem and built a network-level workflow that connected compliance status to the next action.

The system routed delinquent users directly to the work they needed to complete, then restored normal access automatically. It reached 99% compliance across multiple offices and delivered more than $1M in reported annual savings.

A separate labor-pricing platform applied the same principle to fragmented quoting: connect payroll and rate-card data so account teams could see margin implications while decisions were still being made.

Based on production systems delivered for enterprise clients. Proprietary data anonymized.

03 / How I work

Clarity is an engineering discipline.

The technologies change. These operating principles have held across infrastructure, enterprise platforms, data systems, native apps, and AI-assisted delivery.

  1. 01

    Start with the operating truth.

    Before selecting a platform, I find the decision, behavior, constraint, or control the organization actually needs to change.

  2. 02

    Translate in both directions.

    I explain architecture in terms of margin, risk, and continuity, while translating business requirements into terms engineers can implement without guesswork.

  3. 03

    Modernize without breaking the business.

    The best architecture respects current operations, creates a safe next step, and leaves the system easier to change again.

  4. 04

    Stay close to the craft.

    I lead teams and executive decisions, but I still prototype, inspect schemas, review interfaces, test builds, and work through the hard edge cases.

AI-enabled engineering

AI is not the strategy. Better systems are.

I use LLM and coding agents as force multipliers inside disciplined delivery: rich context, explicit architecture, bounded tasks, executable tests, code review, and human accountability. When privacy matters, I also work with local model stacks and controlled integrations.

The advantage is not generating more output. It is shortening the distance between a well-framed problem, a working system, and a decision we can defend.

  1. 01FrameBusiness intent, constraints, evidence
  2. 02ArchitectBoundaries, interfaces, failure modes
  3. 03BuildAgent-assisted implementation
  4. 04VerifyTests, review, visual inspection
  5. 05OwnHuman judgment and accountability

04 / Leadership

The best mentors don’t remove challenges.
They help people believe they’re capable of overcoming them.

People sometimes ask what leadership means to me.

I’ve never believed leadership is about having every answer. Most of the meaningful work I’ve done began with uncertainty. A difficult technical problem. A new product. An unfamiliar technology. An ambitious idea.

Leadership wasn’t pretending to know everything. It was creating enough confidence for everyone around me to keep moving forward together.

Some of the most rewarding moments in my career haven’t happened in conference rooms.

They happened sitting beside someone who believed something was too difficult until they discovered it wasn’t.

Watching someone gain confidence is every bit as rewarding as solving the technical problem itself.

Those moments didn’t begin in the workplace. They’ve always been part of who I am.

Teaching my daughter to build and fly complex FPV aircraft wasn’t really about drones. The drones were simply the classroom.

The real lesson was curiosity. Patience. Confidence. Problem solving. And discovering that difficult things become possible when someone believes you can do them.

When I worked with my older daughter building a large FPV platform, the dynamic was entirely different.

Instead of introducing someone to engineering, we were building together. Designing together. Thinking together. Discussing tradeoffs. Planning. Iterating. Creating. Sharing knowledge openly so that others could learn from our process.

The project became collaborative rather than instructional. Eventually the student becomes a peer. Those are the kinds of teams I enjoy building professionally.

These aren’t isolated family moments. They reflect how I’ve always approached leadership.

At work I don’t simply assign tasks. I mentor. I coach. I explain. I create environments where people can solve problems confidently.

Whether I’m leading enterprise architects, developers, business analysts, finance teams, or introducing someone to engineering for the first time, my philosophy stays remarkably consistent.

Technology changes constantly. Leadership doesn’t.

The tools become more powerful. AI writes more code. Frameworks evolve. Platforms come and go.

But curiosity. Patience. Humility. Listening. Teaching. And creating confidence in other people.

Those qualities never become obsolete.

I hope these films show something that a résumé cannot.
Not simply what I’ve built. But how I build people along the way.

05 / Experience

A career moving closer to the business while staying hands-on with technology.

From infrastructure and operations to enterprise platforms, consulting, and commercial software, the progression has been consistent: broader accountability, deeper context, and continued hands-on practice.

View the one-page résumé
  1. Founder & Principal Architect

    Carabuilt Consulting · TayzoWare

    Enterprise architecture and decision-intelligence consulting, alongside end-to-end ownership of native commercial software.

  2. Director of Business Systems

    Dentsu

    Led cross-functional platform modernization, financial systems, data, automation, and integration work across a complex multi-brand environment.

  3. Director of IT Operations

    mcgarrybowen

    Modernized infrastructure, security, compliance, and service delivery through a period of rapid agency growth.

  4. Senior Systems Engineer

    mcgarrybowen

    Built resilient cross-platform systems, storage, automation, and creative-media infrastructure.

  5. B.S. Computer Science

    New York Institute of Technology

06 / Range

Comfortable at every altitude.

Leadership & strategy
Technology roadmaps, operating models, executive communication, PMO governance, change leadership, M&A integration, mentoring
Enterprise architecture
Financial and business systems, integration strategy, data modeling, identity and access, workflow automation, resilience, vendor platforms
Data, AI & automation
Power BI, SQL, semantic models, LLM workflows, local model stacks, Python, agentic software delivery, decision intelligence
Product engineering
Swift, SwiftUI, StoreKit 2, on-device speech recognition, media pipelines, networking, API design, UX, subscriptions, App Store delivery
Enterprise platforms
Dynamics 365, Workday, SAP Concur, NetSuite, Nexelus, Microsoft 365, SharePoint, Power BI, Active Directory and SSO

07 / Let's talk

Complex mandate?
That’s usually where I’m most useful.

I’m exploring senior technology leadership roles such as CTO, VP of Engineering, Enterprise Architecture, Platform, Business Systems, and AI transformation, as well as selected advisory work where architecture and execution need to meet.

[email protected]

The story behind the work

Meet Michael

Interactive Pricing Demo

Labor Pricing System

Demonstration rebuilt from production work using representative data. Client names, financial information, and proprietary business data have been replaced to protect confidentiality.

Interactive Financial Intelligence Demo

Executive Finance Intelligence

Interactive demonstration created from real production architecture using sanitized sample data. Proprietary client information and sensitive business logic have been removed or anonymized to protect confidentiality.