About
Technology executive. Practical operator. AI transformation leader.
Mark Dos Santos has spent his career building and leading technology across software development, supply chain systems, retail operations, ecommerce, engineering organizations, and AI transformation. He now brings that operating depth to growing companies as a fractional technology executive.
Why The Background Matters
Experience across the places scale problems actually show up.
Background
The combination that matters for mid-market technology leadership.
Most technology scale problems cross multiple functions — business strategy, system architecture, vendor relationships, team capacity, and delivery governance. Mark's career has been built across all of them.
Mark has held executive technology leadership roles in mid-market and enterprise environments, directing software teams, managing vendor portfolios, and steering large-scale transformation programs. His most recent hands-on operating background includes leading a 47-store Shopify POS transformation across a national retail chain — managing technology, vendor relationships, store operations change, and phased rollout across the full network.
He also designed the technology and operating model for a 45-location omnichannel fulfillment network, including store-based fulfillment routing logic, SLA design, and the ecommerce and inventory integrations that made it work at scale.
He now works with CEOs, founders, COOs, and operators through Cloudstruct Solutions Ltd., his consulting practice. Engagements combine strategic clarity, operating structure, and implementation oversight — from diagnosing the real problem to keeping delivery connected to business outcomes.
Career Arc
Five stages that built the operating depth.
Each stage added a layer that the others cannot replace. The value is in the combination.
Software and systems foundation
Started in hands-on software development and systems integration — building the technical judgment that still anchors every engagement.
Supply chain and ecommerce systems
Led technology across complex fulfillment operations, inventory systems, and ecommerce platforms. Learned where the real operating risks hide.
Retail technology and omnichannel operations
Directed technology across national retail environments — POS systems, store operations, fulfillment networks, and the integrations that tie them together.
Executive IT and engineering leadership
Held senior technology leadership roles responsible for strategy, vendor relationships, team development, delivery governance, and board-level communication.
AI transformation and agentic workflow strategy
Now working at the intersection of executive leadership and practical AI adoption — helping companies move from AI interest to governed, measurable business value.
Differentiators
What makes this engagement model different.
The value is not a single skill — it is the combination of executive communication, hands-on technical background, AI fluency, and operating experience across retail, ecommerce, and software delivery.
Executive communication with technical depth
Comfortable in boardroom conversations and architecture reviews. Can translate between what executives need to decide and what engineers need to build.
Retail and ecommerce operating experience
Direct experience leading technology across stores, fulfillment networks, and ecommerce platforms — not just advising from the outside.
AI strategy grounded in workflow reality
Positions AI as a workflow and operations problem first. Governance, adoption, and measurable ROI matter as much as the technology selection.
Software delivery discipline
Built and led software teams. Understands delivery constraints, technical debt, vendor dynamics, and what separates a functioning roadmap from a wishlist.
Business-to-engineering translation
The most consistent value: helping executive teams make faster, better technology decisions by connecting business priorities to implementation reality.
Fractional engagement model
The benefits of a senior technology executive without the timeline, cost, or organizational overhead of a full-time hire — calibrated to where the company is today.
Best Fit
This works best when technology is already important.
The strongest engagements are with growing companies where technology is already a factor in revenue, operations, customer experience, or risk — and where the leadership structure has not kept pace with the complexity. That gap is where the most leverage exists.
- CEOs who need technology clarity without hiring a full-time CTO
- Founders managing technical teams or vendors without a technical executive
- Operators preparing for AI adoption, platform modernization, or scale
- Companies where technology decisions are reactive rather than strategic
Operating Model
How an engagement typically works.
Most engagements start with a strategy call and a focused assessment — establishing shared understanding of the business context, operating constraints, technology risks, and the highest-value next moves. From there, the work can follow a fractional leadership model, a focused project, or a combination.
Ready to discuss the technology leadership your business needs next?
Book a strategy call to clarify the business problem, the technology risks, and the highest-value next step.