Ideas and Insights
Resources for technology and digital leaders
How to Build a Product-Led Operating Model That Actually Sticks
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.
Exploring Transformation Leadership
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.
How to Implement Digitization with Low Investment and High Return
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.
Debunking Operating Model Transformation Myths
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.
Driving Business Success through Digital Evolution
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.
Navigating a Digital Transformation
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.
Dispelling the Digital Transformation Myth
Jen joins Kurt Schmidt on the Schmidt List podcast to challenge the conventional wisdom around digital transformation — and make the case that technology investment alone is never enough. They dig into why so many transformation efforts stall, what leaders get wrong when they treat it as an IT problem, and what it actually takes to build the organizational and cultural conditions for lasting change.
Product Leadership Tips from a Guide to CTOs
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.
Small Bets Placed Often: Using Digital to Transform Your Business
Jen joins Kathy Hollenhorst and Gino Giovannelli on In the Key of D to discuss digital risk and reward, how she helps companies integrate digital into their business strategy, and why projects end but products endure. The conversation covers everything from what holds companies back from meaningful digital integration to what it actually looks like to bring Agile principles out of IT and into the whole organization.
Product Management is Negotiation
Jen joins Kurt Schmidt on the Schmidt List podcast to explore two skills that don't always get talked about together: networking and negotiation — and why both are essential to a product management career. Speaking from her role at the time as VP of Digital Product Management at Optum, Jen shares how she's built and sustained meaningful professional communities, and why taking ownership of your own growth is the only strategy that actually works.