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Headstorm strategized, planned, and executed improvements to the IT organization and the systems/services it provides to the company.


We developed an execution roadmap that enables a new culture in the organization where IT focuses its resources on the priorities for the business and moves to improve competitiveness

Optimize through accountability

Greater accountability for initiatives to finish on-time and on-budget

Prioritizing innovation

Invested resources to stand up a cutting-edge analytics platform that will drive artificial intelligence to vessel services

Simplified architecture

Simplified the enterprise application architecture to focus budgets on innovation

Reduced time

Implemented new ways of working that reduced the time investments of business stakeholders while also improving the velocity to deploy new solutions


New Canaan, CT

Our client is a 160-year-old marine transportation and maritime services company that saw the existential threats of autonomous vehicles and artificial intelligence. They chose Headstorm to help them create a 1–3-year technology roadmap and budget that would transform IT from a burden to the business into an enabler of the business.

  • Interim Chief Information Officer
  • Development Principal Architect
  • Product Portfolio Management
  • Cloud Infrastructure Architect
  • Agile Scrum Team for Analytics Platform Development
Build type
  • Greenfield
  • Brownfield
Tech stack
  • Multicloud AWS/Azure
  • Microsoft .Net
  • SQL Server
  • Microsoft Dynamics 365

What we did

Getting the full picture

Started by understanding the business strategy, including the strengths of the company, gaps in capabilities, and opportunities in the marketplace.

  • Interviewed key IT personnel and “customer” stakeholders
  • Performed map/gap against best practices from transportation/ supply chain industry and beyond

Testing hypotheses and building consensus

Headstorm utilized hypothesis-driven consulting methods to hypothesize new ideas and direction that may shape critical components of a strategy, then gather data to support or disprove it.

  • Developed 6 hypotheses to improve IT based on assessment
  • Developed key alternatives for leadership consideration
  • IT Organization
  • Operating Model
  • New technologies and innovations to strive for
  • Simplification of the enterprise IT architecture

Roadmap to the future

Headstorm planning included implementation roadmaps that take resources, timelines, and budgets into account:

  • A technology roadmap, definition of various projects
  • A resource plan outlining key roles & responsibilities
  • Identification of risks/issues
  • A budget providing financial earmarks for future IT spend

Practical First Steps

Plans are difficult to implement unless there are tangible, practical steps that people are willing to support and help generate progress. Headstorm provided a set of first steps defined to begin execution of a new strategy that gains positive momentum.

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