What happens when your roadmap looks great on paper, but your team seems reluctant about it? You may hear them questioning why this platform, this reorg, this operating model change will be the one to finally fix things. If you're a CIO or CTO who's been through more than one of these modernization cycles, you know the feeling I’m describing. But what if I told you that this phenomenon has a name, and it’s just as costly as your tech debt? It’s called emotional debt. Here, I'll show you how to spot it, along with my favorite 3-step exercise for getting out ahead of it.

Transformations fail constantly — not because of bad intentions, but because most organizations mistake activity for change. Jen joins Lily Smith and Randy Silver on The Product Experience to break down why transformation initiatives stall, what "transformation theatre" actually looks like from the inside, and what it genuinely takes to build a product operating model that holds.

Jen joins Dave Sobel on the Business of Tech podcast to challenge how leaders think about digital transformation. They dig into what operating model transformation actually means, why legacy companies in "boring" industries are often the most exciting places to work, and how strategic partnerships with managed services providers can accelerate meaningful change.

This article covers the hard truth that “mature” is a bit of a fallacy for product-led organizations. Learn why “sustaining” is actually what you’re after, the three key behaviors that must be prevalent in your organization to maintain success, and the KPIs and green flags that indicate forward momentum. 

Running a team, an IT practice, or an entire organization can sometimes be a lonely job.  As we close out our second year at Tuckpoint Advisory Group, I find myself reflecting on a journey marked by scaling pains and, at times, burnout and overwhelm. In that spirit, I’m sharing three actionable insights you can put into practice to scale more smoothly and navigate the sometimes lonely road of leadership.

Learn about the four stages of Digital Transformation and identify the common transitions that stump teams and block momentum on the road to building a mature product-led operating model.

Jen joins Tim Butera of AgileDrop to make the case that transformation doesn't have to mean big spending. They dig into why the current economic climate makes internal transformation smarter than ever, how legacy companies can close the gap with digital-native competitors, and what it actually takes to get Agile and product management to stick — beyond just sprinkling on the pixie dust.

In this article, you’ll learn why transforming your financial model is necessary to become a high-functioning product-led organization, as well as the mindset shifts required to unlock increased efficiency, flexibility, and long-term value creation.

Jen joins Deb Reuben, CEO of TomorrowZone, to challenge that assumption. They dig into the myths that derail transformation efforts and make the case for why the human side of change isn't a soft concern — it's the whole game. Jen also brings a perspective you don't hear often: why constrained, regulated environments are actually where the most interesting transformation work happens.

This article sheds light on the concept of governance in Digital Transformation and Operating Model Transformation, why it’s so important to get it right, and the small shifts you can start making today to improve your processes and see better results.

Many companies have started return-to-office initiates, mandated in-person attendance, and are shifting back to pre-pandemic norms. But is it the right play? Today’s article explores this misstep with specific regard to Digital Transformation and sheds light on the significant opportunity leaders have to reimagine the way teams work to build resilient structures that take them into the future.

Jen joins the Conquer Local Podcast to explore what it actually takes to drive business success through digital transformation — and why so many organizations fall short. The conversation digs into why companies that focus narrowly on technology miss the operational and human elements that determine whether transformation efforts succeed or stall, and what it looks like to take meaningful action instead.

When it comes to digital transformation, many organizations try implementing Agile and Product sequentially, doing one first then following up with the other. In either of these approaches, something is missing from the landing. Today's article shares a proven technique for layering in Product and Agile coaching to make digital transformation efforts significantly more effective.

Tuckpoint's Jen Swanson joins the Digital Velocity Podcast to unpack what digital transformation really means, and why most organizations are thinking about it too narrowly. Together, they explore how transformation has to run from the inside out, why prioritization is the hardest part of any change effort, and how the role of outside advisors is evolving.

In the final installment of this series on talent management for digital transformation, we’ll explore the root cause of change resistance, why organizations must address it, and three key elements of successful change-agility frameworks.

The terms Digital Transformation, Business Model Transformation, and Operating Model Transformation are often used interchangeably, but in reality they each represent distinct yet interconnected concepts that are pivotal drivers of change in growing organizations. Here, I define each term and reveal why it's rare – even impossible – to take on any one of these without the others.

Let's dive into the essential Key Performance Indicators (KPIs) you’ll need to consider if you want to stay on track to achieve a successful and lasting digital transformation.

If you’re a leader at the helm of Digital Transformation, you can’t afford to ignore the signs that something is seriously off. Most of these symptoms can be traced back to one root cause, and they need to be addressed so you can get the ROI on your Transformation.

In this article, we explore the driving forces and challenges behind digital transformation for healthcare, as well as promising services that might revolutionize patient care and the healthcare ecosystem as a whole.

If you’re driving Digital Transformation in your org, you likely have a handle on WHAT you need to transform, but are you thinking about HOW you transform? Your answer to that question determines if you’re going to get the ROI on your Digital Transformation investments in the long term and achieve the results you’re seeking.