The Portfolio Executives

Pierre Montersino

Pierre Montersino
  • Specialism: Business and Technology Transformation with a focus on AI, Digital Strategy and Enterprise Modernisation across regulated and complex industries. An Expert in bridging C-suite ambition with delivery reality.
  • Track Record: CIO & Transformation Expert with global leadership roles across Financial Services, Insurance, FMCG and Logistics. Formerly led major transformation and M&A initiatives at NTT Data, TripAdvisor, Bank of England and Specsavers. Trusted advisor to executive teams navigating AI and digital disruption.
  • Offer: I have the following offerings: AI & Digital Transformation, Strategy and Technology-led Business Growth, Initiatives, Turnkey M&A Technology Integration, Global IT Systems Setup & Modernisation, Complex Programme Delivery (incl. Cloud, AI, ERP)  CxO-level Advisory on Change & Innovation  Organisational Design, Operating Model Rebuilds  Leadership Development & Capability Uplift.
  • Pierre says: Transformation isn’t about digitising the old.  It’s about reimagining what’s possible and delivering it at pace. I bring strategy to life, turning AI, automation and technology into board-level outcomes.
  • Try me: https://piermontdc.com/

After more than two decades leading transformative initiatives across industries, I have seen first-hand how organisations often struggle to translate strategic ambition into operational impact. As a CIO and Transformation Expert, I’ve been at the helm of enterprise-wide programmes, mergers and acquisitions, and AI-driven innovation.
What I’ve consistently found most fulfilling is partnering closely with executive teams—repeatedly across different businesses—to drive lasting, meaningful change.

The shift to a Portfolio Executive model was a natural evolution. It allows me to:

  1. Share my expertise across a range of businesses facing complex digital and organisational challenges

  2. Work with agility and precision where the need is most critical — from scaling AI capability to steering high-stakes programmes

  3. Avoid the inertia of long-term roles and instead embed momentum, clarity and commercial impact rapidly

  4. Build deeper, trusted advisor relationships with senior leaders (as a catalyst, not just a consultant)

I’m motivated by the opportunity to step in, stabilise, strategise and scale—then step back once the right foundations are in place. It’s not about ownership or tenure. It’s about impact.

My journey into Portfolio Executive work didn’t begin with a single decision. It evolved through experience, demand and a desire to create greater impact across multiple organisations. Over the years, I led major transformation programmes across industries, often stepping into high-pressure situations where clarity, direction and delivery were urgently needed. Whether it was rebuilding global IT environments from the ground up, integrating complex M&A technology estates, or driving AI and automation strategies for the C-suite, I found myself increasingly being called in for strategic interventions.

As these engagements grew more frequent and often ran in parallel, I realised I was already operating in a portfolio capacity. The difference was that it wasn’t yet intentional.

What truly catalysed the shift was twofold:

  1. Demand: Senior leaders began approaching me not just to run programmes, but to help shape transformation strategy across their business units or even boards

  2. Purpose: I saw an opportunity to work across rather than within organisations to bring fresh, unbiased thinking and create value where it was most needed, without being confined by internal politics or legacy structures

Formalising my work as a Portfolio Executive allowed me to focus on what I do best: partnering with visionary executives, solving complex problems and accelerating change. It’s not about being everywhere—it’s about being where it matters most.

My first real success as a Portfolio Executive came when I was brought in to stabilise and transform the IT landscape of a business undergoing rapid expansion following a complex M&A deal. The company was grappling with fragmented systems, siloed operations, and a lack of clear digital direction—all of which were stalling integration and threatening future scalability.

I was initially engaged on a short-term advisory basis. However, within weeks it became clear they didn’t just need advice—they needed delivery. I stepped in as a transformation lead, worked alongside C-suite stakeholders and within 90 days had:

  • Defined a post-merger IT and digital strategy that aligned to the business’s new commercial vision

  • Orchestrated a full programme mobilisation covering infrastructure, data, cloud and cybersecurity

  • Unified previously disconnected teams and suppliers into a delivery-focused operating model

  • Introduced governance structures and performance metrics that gave the board confidence in execution

The result: a successful integration, uplift in delivery confidence, and the foundations laid for scalable growth—all achieved without the typical consultancy overhead or internal resistance. This experience was pivotal. It proved that my ability to step into complex environments, establish clarity and lead high-impact delivery could provide immense value, fast. It confirmed that the Portfolio Executive model wasn’t just viable—it was needed.

Throughout my journey—from leading enterprise-wide transformations to becoming a trusted Portfolio Executive—I’ve learned that successful change is never just about technology. It’s about people, pace and purpose.

Here are the key lessons that continue to shape how I operate:

  • Strategy is easy — execution is everything. Bold visions often fall apart in delivery. I’ve learned to bridge that gap with practical frameworks, clear governance and relentless focus on outcomes.

  • Culture can accelerate or kill transformation. No matter how brilliant the solution, if it doesn’t align with the organisational mindset or leadership behaviour, it will stall. I now focus as much on shifting thinking as I do on shifting systems.

  • Speed matters, but not at the expense of direction. In high-pressure environments, there’s a temptation to act fast. But I’ve learned that clarity before velocity is what prevents costly course corrections later.

  • Executive alignment is non-negotiable. I’ve seen transformations succeed not just because of funding or frameworks but because the C-suite was aligned, engaged and accountable. My role is often to facilitate that alignment from the outset.

  • Impact beats involvement. As a Portfolio Executive, I’ve learned the value of being the catalyst, not the controller. My success is measured by the legacy I leave behind (capability, clarity and confidence), not by how long I stay.

Ultimately, I’ve learned that transformation isn’t just a project—it is a mindset. My job is to embed that mindset into the organisations I serve. This approach works now because the world has caught up with the kind of leadership I’ve always delivered. Organisations are looking for experienced, outcome-driven leaders who can step in, stabilise, and accelerate transformation without the long ramp-up or corporate overhead.

What makes it work now is that I offer clarity in complexity—at a time when many boards are navigating AI, digital disruption and operational volatility. I bring strategic breadth and delivery depth, combining big-picture thinking with hands-on programme leadership. I move with pace and precision, unencumbered by legacy politics or internal agendas. And I’m not chasing titles. I’m focused on impact. In today’s environment, businesses value someone who can embed capability, not dependency. Someone who can lead from the front, advise at the board, and leave the organisation stronger than they found it.

It’s working for me now because I’m doing what I’ve always done—just with sharper focus, broader reach and greater agility. While I’ve delivered transformation at scale and advised some of the most ambitious leadership teams across sectors, what I hope for now goes beyond success—it’s about significance.

I hope to:

  1. Shape more purposeful organisations that don’t just digitise for efficiency but transform for resilience, relevance and real human impact

  2. Work with bold, values-driven leaders—executives who are ready to challenge the status quo, act with urgency and make courageous decisions

  3. Mentor and empower the next wave of change-makers, helping future CIOs, Transformation Leads and AI strategists navigate complexity with confidence and clarity

  4. Build lasting ecosystems, not just projects—environments where innovation, inclusion, and insight become embedded ways of working

  5. Continue evolving myself by staying on the edge of what’s next in AI, transformation and digital leadership, so that I remain not only relevant but valuable

Ultimately, I hope to leave a trail of organisations that don’t just say “we delivered a programme,” but say “we changed the way we think, lead and grow our organisation.”