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.

We’ve long been a culture that loves the story of crossing the finish line. However, radically transforming your organization means you can’t treat it like a sprint. As a leader of this change, your job is to help teams create impact through reps and small, repeated behaviors that are purposeful and intentional. Here are 3 practices you can honor every day to achieve this.

Congratulations! You’ve landed one of the most challenging and rewarding roles in modern business: the Chief Information Officer (CIO). To help you enter with intent, credibility, and structure, Tuckpoint created a checklist that focuses on what actually matters in your first 30 days. Think of it as a practical diagnostic tool designed to surface blind spots, competing expectations, and hidden risks before you place big bets on technology, structure, or operating models.

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.

Tuckpoint Founder Jen Swanson breaks down three key pillars of a strong product strategy and offers her advice on activating them so you can create a high-performing product organization fueled by teams that take the business where you want it to go. 

In this guide, Tuckpoint founder Jen Swanson covers the essential elements of effective change leadership and strategies leaders can leverage to foster a culture of change agility within their digitally-transforming organizations.

If you’re at the helm of a product-led organization, it’s important that you recognize the signs that your product leaders and managers need extra support. In this article, you’ll learn the external and internal triggers that threaten a product practice and, as a result, your product managers’ and leaders’ ability to create effective outcomes for the org. 

The new year has arrived in full swing, and, with it, my predictions for emerging trends in digital transformation and product-led companies in the year ahead. What’s on the horizon? This article explores 5 key areas that will shape digital transformation in 2024.

It’s critical to hire talent with transformational leadership characteristics. But how do you ensure your candidates embody the qualities that actually push transformation forward? And what kinds of questions reveal the skills that aren’t easily bulleted on a resume? Here we explore five transformational leadership characteristics to look for in your next hire, why they’re so critical to success, and how to uncover those qualities during the interview process.

Today’s article is about the role of modern CTOs and the challenges they face when it comes to digital transformation. It includes a list of common struggles that might feel all-too familiar.

Feeling a little stuck, uninspired, or perplexed over your digital transformation efforts? Sometimes one light-bulb moment is enough to reignite the process, which is why we’ve compiled this list of our favorite digital-transformation resources for leaders.

If you think digital transformation is simply about adopting new technologies and digitizing your offerings, you’re missing a huge piece of the puzzle. In fact, Digital Transformation actually has very little to do with technology. What actually moves the needle is a lot more complicated and can be summed up in three core truths.

Jen joins Jim Cuene on the Business Drivers podcast to dig into what it actually takes to lead a digital product transformation — and why the hardest part has nothing to do with technology. They explore the emotional intelligence required to navigate organizational change, what's really going on inside the "frozen middle," and why the skills Jen learned studying adult learning and development turn out to be exactly what transformation work demands.