Digital and Operating Model Transformation Ideas

Find resources and tips for leaders at the helm of Digital Transformation and Operating Model Transformation in product-led organizations.

Katlyn Daoust Katlyn Daoust

Why Your Organization Is Busy But Stuck: How Operating Model Misalignment Shows Up in Everyday Work

Your operating model defines how teams prioritize, make decisions, and deliver value. But what happens when different parts of the company operate according to different and sometimes conflicting models? In this article, we’ll unpack the symptoms of a fragmented operating model, explore how and why these fractures emerge, and examine the real risks they pose to strategy, culture, and customer experience. We’ll also offer a path forward through Operating Model Clarity™.

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Operating Model Transformation Jen Swanson Operating Model Transformation Jen Swanson

Why Transformation Stalls: 6 Complexities Modern Orgs Can’t Ignore

Operating Model Transformation isn’t just about new frameworks or tooling. It’s about confronting deeply embedded ways of working that were designed for a world that no longer exists. And that makes transformation both technically complex and emotionally fraught. In this article, we break down six common complexities that we’ve seen derail teams and stall organizations on the road to becoming transformed.

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Jen Swanson Jen Swanson

The 5 Operational Barriers to Becoming a High-Performing Product Org

Every organization wants to move faster, align better, and unlock more value across its tech and business teams. But most don’t realize how much friction is embedded in the way their organization actually works until they try to change it. This is a roadmap for understanding those friction points. Because naming them is the first step to moving through them.

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Why Empowered Teams Outperform: A CTO’s Guide to Operating at Speed

You say you want to go faster. Every tech leader does. You’ve invested in Agile. You’ve stood up teams. You’ve adopted every methodology with a four-letter acronym promising to be the silver bullet. And yet, things still feel slow and progress starts to stall. The problem isn’t your tooling. It’s not your strategy. It’s your decision-making model. Learn more about leadership’s role in speeding up execution in a way that sticks.

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Operating Model Transformation Jen Swanson Operating Model Transformation Jen Swanson

When Agile Isn’t Enough: The Cost of Operating Model Debt

You’re familiar with tech debt and what it looks like when the codebase can’t keep up with the business. But what if your biggest slowdown isn’t in your tech stack, it’s in how your company works? That’s Operating Model Debt. And just like tech debt, it doesn’t stay hidden for long. So, let’s define Operating Model Debt, how it shows up, and what you can do about it.

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3 Key Takeaways from the 2025 PLA Summit and The New Must-Have Product Operations Skill

This was Tuckpoint’s second year attending and sponsoring the Product Ops Summit, organized by the Product Led Alliance. Here, I’ve boiled down the three most important takeaways, the hot new Product Operations skill you’ll want on your radar as you build your talent bench, and a few actions leaders can take right now to get on the train before it leaves the station.

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The Fallacy of Becoming a “Mature” Product Organization: Secrets From an Operating Model Expert

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. 

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Tips for Technology Leaders on Operating Model Transformation Stakeholder Commitment

If you’re a tech leader tired of hearing the C-suite or business leaders refer to Product Operating Model Transformation purely as a technical initiative, this guide is for you. It will help you understand the “watch outs” and phrases that indicate resistance, how to respond in those instances, and shift mindsets around transformation so it’s understood as everyone’s job (not just tech’s).

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Leadership Jen Swanson Leadership Jen Swanson

Top Skills for Product Leaders in 2025: What’s New?

Does anybody else love using the new year as an excuse to book a retreat in the woods and plan for the year ahead (I do it annually)? As you participate in your own reflection and planning exercises this month, I encourage you to think about what will be required to thrive as a modern product leader in 2025. This article shares my POV on three areas to watch, along with the hard and soft skills you’ll need to cultivate to excel in product leadership this year. 

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3 Actionable Leadership Insights to Scale Your Organization More Gracefully

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.

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The Path to a Modern Operating Model: Navigating Transformational Leadership in Uncertain Times

This year has ushered in some “anti-pattern” behaviors across many product-led organizations, including a natural tendency to default to what feels comfortable and familiar, like command-and-control leadership behaviors. In this article, you'll learn the "watch outs" for defaulting to old ways of working, and the importance and rewards of honing transformational leadership characteristics within your org.

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Outcomes vs Outputs: A Key Mindset Shift for High-Performing Product Organizations

An important characteristic of high-performing product organizations is the company-wide ability to focus on outcomes over outputs. This article will help you understand the importance of focusing on outcomes over outputs, with some initial steps and “watch outs” to follow as you cultivate this mindset across your transforming organization.

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Change Leadership vs Change Management in Product-Led Organizations

When you’re transforming to a product-led organization, change management is futile without the necessary change leadership approach to drive the process. This article details the difference between change leadership and change management, along with the necessary mindset shifts every leader needs to make in order to support a successful transformation toward product-led ways of working.

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