The 90 day plan

Stepping into the role of chief technology officer within the freight and supply chain world is unlike joining any other industry. There is no gentle ramp up, no quiet period, no space to ease yourself into the rhythm. From day one you’re stepping into a landscape of moving parts, competing priorities, legacy systems holding businesses together by sheer willpower, and the relentless pace of daily operations. It’s an environment where even a momentary drop in system stability can halt lorries, disrupt warehouses, delay customs, and fracture customer trust.

That’s why having a clear, disciplined 90 day plan matters. It isn’t a corporate ritual or a leadership cliché; it’s a survival mechanism. It shapes the tone of your leadership, signals intent to the organisation, and provides the structure needed to balance immediate fires with long term strategic direction. What follows is the plan I use when taking on a CTO role in this sector, a plan that focuses not on theatrics, but on establishing clarity, control, and momentum in an industry that rarely stops.

The first month is about understanding the business without trying to change anything too quickly. Freight and supply chain operations hide layers of complexity: regional variations in process, century old workflows, ingrained habits, unofficial workarounds, personality driven decision making, and systems so deeply customised that nobody fully remembers why. You can’t lead effectively until you understand these subtleties. So this period becomes an intensive listening tour. I sit with warehouse teams during peak intake, shadow planners at their busiest, join drivers on early morning runs, and spend long hours with finance, customs, and customer service teams. You learn more in these raw, unfiltered operational moments than any orientation pack could ever reveal.

Alongside this, the first 30 days are devoted to building relationships and trust. Engineers often arrive battle scarred, having endured years of technical debt without the authority to fix it. Operational staff are wary of change that might disrupt the rhythm of the working day. Executives want results yesterday but are often disconnected from the reality of how fragile their systems have become. Establishing rapport open, honest, unguarded rapport, is the most strategic task of the early phase. People need to see that you respect the operation, you understand the stakes, and you’re here to work with them, not around them.

Only once trust is forming does the second phase begin. Days 31 to 60 focus on diagnosis, architecture, and early wins. This is where you begin identifying the systemic issues that have been quietly sabotaging performance for years. Poorly integrated WMS and TMS platforms, daisy chained automations that nobody can troubleshoot, data architecture that collapses under volume, vendor relationships that deliver little value, and teams drowning in operational noise. In this phase I audit infrastructure, data flows, integration points, codebases, security posture, vendor contracts, and team capability. The aim is not to produce a perfect map but to uncover the deepest risks and the biggest opportunities.

During this period, I also look for two or three early wins, small, high-impact changes that signal a new era of momentum. It might be stabilising a critical interface, removing an unnecessary manual process that frustrates warehouses daily, or improving visibility on performance metrics that the board has long wanted but never seen. These are symbolic victories. They show progress without disruption and build confidence in the broader roadmap that is forming.

By the time the final 30 days arrive, the picture is becoming clear. This is the period where strategy crystallises and the foundations of long-term transformation are laid. In freight and supply chain, strategy must be both pragmatic and uncompromising. Overambitious plans collapse quickly in the face of operational reality, while overly cautious plans fail to deliver the modernisation the business desperately needs. My approach is to focus on architecture, autonomy, and ownership.

Architecture matters because most freight businesses are sitting on a patchwork of outdated systems. Without a clear architectural north star, every improvement turns into another short-term patch. In this window, I define target architecture, build the transition pathway, and articulate how we move from monolithic, legacy-bound operations to flexible, integrated, API driven platforms that support automation and scalability.

Autonomy matters because engineering teams often operate as ticket factories rather than platform creators. Transformative technology emerges only when teams are empowered to build, iterate, and innovate with purpose. In the final month of the plan, I reset structures, roles, accountability, and working practices, ensuring engineering becomes a strategic force rather than a reactive one.

Ownership matters because external vendors often hold freight companies hostage with inflexible systems and inflated pricing. While the right partners have value, long-term resilience comes from developing core capability internally. This is where I begin shaping the product mindset moving from buying technology to building differentiating capability, a shift that has saved businesses millions while dramatically improving agility.

By day 90, the organisation should feel the difference. Communication is clearer. Priorities are stabilised. Engineering has regained confidence. Operational teams feel heard rather than disrupted. Leadership has a realistic understanding of investment needs. The strategic plan is grounded in lived operational insight rather than theoretical ambition. And most importantly, the business senses that technology is no longer a blocker or a cost centre, but becoming a lever for competitive advantage.

This plan isn’t glamorous. It doesn’t seek applause. It focuses on the realities of an industry where uptime is sacred, efficiency is survival, and technology must evolve without breaking the rhythm of daily operations. Over the coming months on Diary of a CTO, I’ll be diving deeper into each part of this plan how to diagnose broken systems, how to establish engineering culture, how to rebuild architecture, and how to drive transformation in a landscape shaped by legacy, expectation, and constant motion.

A CTO’s first 90 days in freight and supply chain is a balancing act between humility and authority, patience and pace, preservation and transformation. It sets the direction of the next three years, not just the next three months, and done well, it lays the groundwork for a technology function that empowers the entire organisation to operate with clarity, confidence, and resilience.