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Four conversations diving deep into the most exciting frontiers of digital transformation


Five months ago, OZ launched Transformation Matters, a podcast hosted by OZ Chief Transformation Officer Dr. Paul Bailo devoted to in-depth conversations with the fascinating visionaries out on the cutting edge between tech innovation and our everyday lives.

If you missed the early episodes, don’t fret: We’ve pulled together five of the best in one place for you to conveniently visit—or revisit—as you work to navigate your own day-to-day.

1. InnSure Executive Director Talks to OZ about the ROI of “Tree Hugging,” How the Insurance Industry Will Supercharge the Fight Against Climate Change, & More

“Are you telling us that the insurance industry is treehuggers now that they’re advocating for the environment?”

This is the good-naturedly provocative question Bailo puts to InnSure Executive Director Charlie Sidoti in this informative and entertaining inaugural episode.

“It’s in their best interest,” Sidoti responds, giving as good as he gets. “I’ve always been environmentally conscious, but it’s not just about doing good for the sake of being a good person. The UN suggests that there’s going to be $5 trillion a year spent on climate. Suppose Property & Casualty (P&C) captures 2% of the global economy. In that case, we stand to capture $100 billion in new business.”


2. My New Coworker Has No Heartbeat

How does a “fast-talking guy from New Jersey” with a degree in International Economics from NYU end up being one of the driving forces in the conversational AI revolution?

It’s a fascinating and illuminating journey that Bailo teases out of guest Steve Hartenstein, Senior Director of Autonomic, Analytic, and Cognitive Solution Design at IPsoft.

“Ironically, the very same guy who had gotten me to work in his dad’s computer store had developed something called Active Buddy in the early eighties which was a wiseguy chatbot,” Hartenstein tells Bailo. “When you asked it questions it would do basic web searches to try to find your answers but mostly it was a sarcastic, annoying utility that demonstrated that, frankly, voice as an interface was going to establish primacy. It took a while for it to happen, but I think that’s a lot of what’s behind the success of conversational AI today.

“Voice is becoming the interface of preference,” he adds, “and telling an application what you want is probably the most effective way to let a human being interact with an application.”



3. How Technology is Extending & Reshaping the Future of Our “Golden Years”

Is ninety the new forty?

And if so, what does this vast extension of our golden years mean—economically, philosophically, and practically—for the institution of retirement?

On this episode of Transformation Matter, an enlightening, sobering, and, ultimately, hopeful conversation with Nassau Financial Group Chief Marketing Officer and host of That Annuity Show Paul Tyler about this moment of societal change, as profound as it is inevitable—and how technology, properly designed and engaged, can help us navigate it.


4. How technology can help you rediscover the “sparkle” in your life and career

On her LinkedIn bio, Robin Kirby describes herself as a “former CHRO turned entrepreneur and happier person to be around.”

The road from the former to the latter, however, was no easy journey: After more than two decades and fifty thousand hours of high-level HR work at companies such as Citigroup, GE, Infosys, USAA, and others—Kirby came face-to-face not only with her mortality but also a work/life balance that had gone seriously awry.

“Like a lot of your listeners, I spent so much of my career scaling mountains, hitting new goals, and all those things,” Kirby tells Bailo on the latest episode of Transformation Matters.

And then, at forty years old, she ended up in the ICU with pulmonary embolisms.

“It was very scary and probably connected to my travel and flying and stress and a lot of things I had going on,” she says. “You would think that kind of life whack would make you pause and listen, but for me, it didn’t. What I did instead—like any good, self-respecting workaholic—was to just pour myself into my job and try to find a way to hustle harder and do more things. Until at some point, I just hit this wall and was kind of curled up in the corner in a fetal position. I thought, ‘What am I doing?’”

The story of her rise from this rock bottom to a true change agent in her former industry is told in Kirby’s affecting, inspiring, and perception-shifting new book, Sparkle: How to Beat Burnout, End Exhaustion and Find a Career that Lights You Up.


5. From “life expectancy” to embracing higher expectations of one’s life

Dedicated to supporting “the global community of those who break barriers and go beyond borders,” Insured Nomads, employing cutting-edge technology and old-school empathy, seeks to elevate and evolve the insurance experience “for those who travel and encounter the unexpected, the unplanned, or the catastrophic.”

“We actually started our organization just at the beginning of the pandemic,” Insured Nomads President and Chief Innovation Officer Allen Koski tells Bailo. “We saw people working remotely, leaving larger companies, saying, ‘You know what? Instead of working in San Francisco as someone who does taxes, I could probably work in a great surfing spot in Costa Rica. When it rains, I’ll do the taxes and when it’s sunny I’ll go surfing, eat ceviche—live the dream. And we wanted to support more people in living those dreams.”

It is a fascinating, fun, revealing conversation that demonstrates just how real the possibility of shifting from a paradigm of focusing on life expectancy to one of embracing higher expectations of life.