Making the Impossible Possible: Orchestrating an AI Transformation May 9 2024
By Rob Tyrie (A Builder)
“Pass me the box of chalk, and that eraser…” As I stood in front of the executive team, the weight of the challenge ahead felt daunting. Our customers’s core software, the backbone of our company’s operations, was due for a major overhaul. Legacy systems built on brittle-old code needed to be reimagined for the AI era. Failure was not an option – billions of dollars were at stake.
This was the kind of high-stakes, high-pressure situation that would test the mettle of any leader. But as I looked around the room at the assembled talent, I knew we had the right people. What we needed was the right approach – one built on openness, mutual respect, and an unwavering commitment to working as "One Team."
The Path to Delivery
Early on, I laid out a core philosophy: "We had a good day. Plans come together. The team delivers. Promises made and promises kept. We got closer." It was a reminder that success would hinge on disciplined execution, trust in one another, and a shared sense of forward momentum.
Managing the uncertainty of such a complicated undertaking is par for the course in my line of work. But this project represented something more – a chance to bring transformative AI technology to an industry still relying heavily on legacy systems. I've spent my career making next-gen software work for the insurance world, and this challenge quite literally thrilled me.
One of the first lessons I've learned is that adversarial, zero-sum approaches rarely work in the enterprise world. You can't bully or bluster your way to shipping multimillion-dollar software. Instead, the path forward requires patience, emotional intelligence, and a "relentless ability to execute" as part of a unified front.
This was the antithesis of the stereotypical "AI disruption" narrative of plucky startups upending industry giants. We were the giants, and the startups were us – an intrapreneurial movement from within, working to transform a core business line using the latest technologies. It would take the coordination of diverse personalities and roles – executives, engineers, consultants, and more – to make it happen.
The Art of Orchestration
Orchestrating this "One Team" effort across corporate silos and competing interests is perhaps the greatest leadership challenge. On one side were the revenue-focused business leaders, intent on protecting the bottom line. On the other were the technologists, eager to implement cutting-edge AI capabilities. Bridging that divide required give-and-take from both sides.
With the business leaders, I knew I had to assuage concerns over risk, cost, and business disruption. I made it clear that this was not about ripping and replacing entire systems in one big bang, but a phased, incremental approach that would protect revenue streams. We would inject AI capabilities into user workflows in a carefully sequenced manner, minimizing friction for stakeholders.
At the same time, I empowered the technologists to explore ambitious AI applications– from computer vision for intelligent document processing to machine learning models for predictive risk scoring. However, I also instilled a sense of real-world constraints. Academic proofs of concept would not work here, people weren’t abstract enough, we need concrete,. transparent and visual tantalizing POC’s; solutions had to be tested scaled, instrumented, production-hardened and based on transparent, accountable systems design principles.
The real magic happened when these all the camps started working together, with business prioritizing use cases and technologists building prototypes in close feedback loops. Different companies, disparate backgrounds, Specific AI models and deployment architectures emerged from this collaborative process. What could have been an ivory tower exercise instead became grounded in pragmatic business realities.
This "One Team" ethos extended far beyond the company walls. Our strategic partners – from major cloud providers to niche AI startups – became extensions of our own workforce, bound by a shared mission. I invested heavily in these external relationships, fostering openness and transparency. I made it clear that this was not about extracting maximum profit, but rethinking how we all create value in a new technological paradigm.
The results spoke for themselves. What seemed impossible just months earlier started becoming reality. A steady cadence of production releases incorporating AI began revamping our software stack and upleveling UX across web and mobile apps. The technology delivered on its promise of raising workforce productivity, improving decision velocity, and enhancing customer experiences.
Making It Work, Together
Those early successes validated our "One Team" philosophy. They proved that big, transformational changes can happen within a large enterprise – not through confrontational tactics or disruptive heroics, but good old-fashioned teamwork, relationship-building, and mutual accountability.
As the project timeline stretched into months, We had to remain vigilant in reinforcing these core principles. Speed, Completeness, Transparentcy, Agility, And Empirical basics. Science. Priorities shifted, executives shifted, budgets got reallocated – but the team’s mission persisted. We recalibrated strategies and reset expectations, but never lost sight of delivering on our promises to one another and our customers.
That sense of shared purpose became its own "flywheel," fueling increasingly ambitious phases of the digital transformation roadmap. What started with low-hanging fruit like text extraction and smart data capture grew into more advanced use cases – intelligent virtual agents, predictive analytics for risk modeling, and AI-augmented underwriting decisioning. Relentless innovation, proven with revenue growth and speed to market..
Each new release reinforced our credibility, giving us broader organizational support to invest in more advanced AI engineering and data management capabilities. We built reusable AI platforms, launched machine teaching practices, and optimized for scalable, secure, and compliant AI deployments across public cloud environments.
Thanks to this compounding momentum, what once seemed like an overly ambitious "moon shot" revealed itself as an evolutionary, step-by-step journey over time. There were no Eureka moments or silver bullets – just the byproduct of tireless teamwork and the patient layering of AI capabilities onto our business.
A Relentless Pursuit
As I think back on that first meeting years ago, the challenges we faced seemed insurmountable at times. Transforming entrenched technology and Human Systems on this scale – all while keeping a multi-billion-dollar business running seamlessly – felt like attempting to rebuild an airplane midflight.
But that's the burden of leadership, especially in this era of rapid technological disruption. You have to make the impossible possible through sheer force of vision, influence, and commitment to "One Team" execution. It's a relentless pursuit where you can never go it alone or fall back on adversarial, zero-sum tactics.
Business today isn't just about relationships – it's about optimizing those relationships for mutual benefit each and every day. Staying true to that dynamic philosophy allowed us to orchestrate a symphony of technology, people, and processes to deliver transformational outcomes.
Looking ahead, AI and modern flexible component roadmaps will only grow more ambitious. But thanks to the strong foundation we’ve laid, we’re prepared to tackle those challenges as "One Team." Because at the end of the day, that’s the real secret to making multimillion-dollar software sing – having promises made, and keeping every last one of them.
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Rob Tyrie is a Software-Sherpa and an entrepreneur. I run a multi-million dollar programs across multiple teams and organizations to create software platforms that are resilient and that last. Generative AI is making that fun again. See more on www.ironstoneadvisory.com 🧠🤖
