Own Your AI Future

Seventy-three percent of employees say AI skills are crucial for their roles. Only 25%, however, have received any training. Mid-career workers and career-changers are left scrambling to upskill on their own, often getting stuck with ChatGPT experimentation while their industries race ahead. In this critical discussion, Polly Allen, Founder of AI Career Boost, and award-winning journalist Ramona Schindelheim confront the absence of clear employer guidelines, the high-stakes expectations workers face, and the free, accessible resources that exist but remain underutilized. Whether you’re a worker wondering where to turn or a leader trying to build an AI-ready workforce, this conversation reveals why closing the training gap is no longer optional.

This interview is the third in a 4-part series generously sponsored by T-Mobile.

WHAT AI LITERACY REALLY MEANS

SHADOW AI: WHO’S REALLY IN CONTROL?

NOT A JOB APOCALYPSE. A PARTNERSHIP.

SIGN UP FOR UPDATES ON FUTURE SERiES

Polly M. Allen

Polly M. Allen has spent over 20 years building and leading software teams, most recently as a Principal Product Manager at Amazon Alexa, where she guided cross-functional science and engineering groups at the cutting edge of AI. She specializes in natural language applications—search, discovery, understanding, and generation—and in 2020, she led the launch of Alexa’s first automatically generated web content summaries (yes, powered by the same transformer technology behind today’s ChatGPT).

But Polly’s story isn’t just about technology. After years in the deeply technical world, she became convinced that the future of AI shouldn’t be shaped only by coders and data scientists. The biggest breakthroughs will come when product and business leaders—those closest to customers, strategy, and impact—have the tools and confidence to lead AI initiatives. That belief drives everything she does today.

Now, through her company AI Career Boost, Polly helps experienced leaders step into AI roles and lead AI product development with confidence—without needing a computer science degree. She also hosts two podcasts, AI Product Leader and AI Afterhours, where she shares insights, stories, and candid conversations about building the future of AI.

An experienced angel investor and past corporate board member, Polly has advised startups, spoken at global conferences, and earned degrees from MIT, the University of Victoria, and UBC. Above all, she’s on a mission to open the doors of AI leadership to a far wider range of thinkers and builders—and to make sure the next wave of AI innovation is driven by leaders who understand both people and technology.

Polly holds a M.Sc. in Software Engineering from MIT and the University of Victoria, and an MBA from the University of British Columbia.

Ramona Schindelheim

Ramona Schindelheim is an Emmy and Peabody award-winning journalist and storyteller who has worked in network, cable, and local television news and digital media. She writes about initiatives, programs, and people preparing workers for quality jobs that provide economic stability and mobility in her monthly LinkedIn newsletter, The Future of Work(ers). Ramona also hosts Birds & Nerds, a podcast exploring the sometimes hidden connection between birds and the bigger world around us.  You can connect with Ramona through LinkedIn, her website, and her Birds & Nerds podcast.