Why Digital Transformation Struggles (And It’s Not What You Think)

Who Really Decides the Winners in Enterprise Software?

For decades, analyst firms like Gartner, Forrester, and IDC have played a critical role in enterprise technology decisions. But as software becomes easier to build, test, and deploy, an important question is emerging: Are analysts still the main signal of credibility in enterprise tech? In this episode of The War Room, Elena Georgieva speaks with Elena Hutchison, former Chief Strategy Officer at Medallia, about the evolving role of analyst relations and how companies should think about analysts in a rapidly changing technology landscape. They explore difficult and often uncomfortable questions, including: • How analyst relations influences enterprise strategy, M&A, and product development • Whether proofs of concept and product-led growth are changing how software is evaluated • Why some innovative companies may never appear in traditional analyst reports • How AI could reshape the role of analyst relations professionals • When analysts provide real strategic insight — and when companies may need other signals This conversation takes a thoughtful look at how enterprise technology markets are evolving and how organisations can navigate credibility, innovation, and market intelligence in the years ahead.

Why Digital Transformation Struggles (And It’s Not What You Think)

Digital transformation isn’t failing because of technology. In fact, most organisations already have the tools, platforms, and budgets in place. So why do so many transformation efforts stall, lose momentum, or quietly fade away? In this episode, we explore the uncomfortable, but liberating, truth: digital transformation is rarely a tech problem. It’s a clarity, alignment, and support problem. We talk about: - Why “legacy systems” are often used as a convenient explanation - The hidden pressure leaders face when driving transformation - The gap between strategy decks and operational reality - Why capability and support matter more than new platforms - What actually moves transformation forward sustainably This is not about blaming executives. Most leaders are navigating complexity without the structure, language, or backing they need. If you're a CEO, CIO, transformation leader, or advisor trying to move from ambition to execution, this conversation will challenge assumptions and offer a more human, practical way forward. Digital transformation isn’t about installing technology. It’s about enabling people to lead through change.

The Analyst Relations Blueprint: From Insight to Influence

Discover why analyst relations is more than PR; it’s a strategic superpower. Bloomberg's Alyssa Gilmore shares how analyst insights shape products, influence executives, and build trust that lasts a lifetime. What’s the real difference between media relations and analyst relations, and why does it matter for your business strategy? In this episode, Elena Georgieva sits down with Alyssa Gilmore, Global Head of Communications for Bloomberg’s financial products, to explore the hidden power of analyst relations. With over 30 years in financial technology marketing and communications, Alyssa shares how analyst insights can shape product strategy, influence executive decision-making, and strengthen long-term trust with stakeholders. She explains why analyst relations is not just about visibility, but about building relationships that last a lifetime. 💡 Key themes you’ll hear in this episode: * The difference between analyst relations and traditional PR * How analyst feedback informs product and go-to-market strategies * Training teams to engage analysts vs. journalists * The role of AI in reshaping analyst relations * Practical advice for startups and scale-ups on when to engage analysts * Why analyst relations is a strategic superpower inside organisations Whether you’re a communications professional, a startup founder, or simply curious about how industry analysts shape markets, this conversation will give you fresh insights into the value of analyst relations today.