How to Know If Your Team’s Ready for AI in PM Software
The AI hype in project management software is real—but is everyone ready for it? In this episode, Galen sits down with returning guest Olivia Montgomery, Associate Principal Analyst at Capterra, to explore the findings from her 2025 Project Management Software Trends Survey. They unpack the real reasons behind the surge in demand for AI-enhanced PM tools and the foundational work teams need to do before expecting AI to deliver real ROI.Together, Galen and Olivia dig into what "AI readiness" actually looks like—technically and culturally. They discuss how competitive FOMO, billion-dollar marketing campaigns, and shifting economic investments are driving decision-making at the executive level, while the realities of adoption, data governance, and employee empowerment are playing out on the ground. They also take a thoughtful look at how PMs can avoid common pitfalls (like AI hallucinations) and begin to build workflows that align with both human and machine strengths.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Olivia on LinkedInCheck out CapterraOlivia’s report, AI & Security Are Top Concerns in Capterra’s 2025 Project Management Software Trends SurveyÂ
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How to Start a PM Career When Generative AI is Replacing Entry-Level Roles
The entry-level project management job isn’t what it used to be. With AI automating many of the classic coordinator tasks, the ground floor seems to have disappeared—leaving aspiring PMs wondering how to even get started. In this episode, Galen Low sits down with Benjamin Chan, Founder of CLYMB Consulting, to unpack what this shift really means for junior PMs, hiring managers, and the next generation of project leaders.Together, they explore how AI is reshaping the role of the project coordinator, what skills and traits are most valuable in today’s job market, and how organizations can reimagine career paths to make sure talent isn’t left behind. Whether you’re breaking in, hiring, or mentoring, this conversation is full of real-world perspective and actionable ideas for navigating the new career landscape.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Ben on LinkedInCheck out CLYMB Consulting
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Turning AI Experiments Into Agency Impact: Transforming Curiosity Into Measurable Results
Experimenting with AI is exciting—but how do you make the leap from tinkering to transforming agency operations at scale? In this conversation, Galen Low brings together Melissa Morris (Agency Authority), Kelly Vega (VML), and Harv Nagra (Scoro) to talk about how agencies can carve out space for experimentation, align AI use to business goals, and actually implement the good ideas that emerge.The panel shares stories of saving hours on PM tasks, setting up accountability frameworks, and creating safe spaces for knowledge-sharing. They also surface the tough stuff—fear of job replacement, cultural resistance, governance challenges—and how to navigate it with clarity and empathy.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Melissa, Kelly, Harv on LinkedInCheck out Agency Authority, VML, Scoro and The Handbook: Agency Ops podcast
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How AI Leadership Shapes Project Delivery (and When You Need It)
When is the right time to hire an AI leader, and what do they actually do once they’re in the door? In this episode, Galen Low sits down with Tim Fisher, VP of AI at Black & White Zebra, to unpack the real-world impact of AI leadership roles. Together they explore the tension between hype and practicality, the mix of skills needed to bridge tech, business, and people, and why AI leadership is less about flashy experiments and more about building trust, change readiness, and operational maturity.Tim shares candid insights from his own path into the role, offering a grounded look at how organizations can approach AI without losing sight of their business goals—or their people. If you’ve ever wondered whether a VP of AI is a made-up job, or how AI leadership can actually smooth project delivery, this conversation is for you.
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Why Automating Everything is The Wrong Move (And What to do Instead)
AI is not eating all the jobs—but the story is more nuanced than the headlines suggest. In this episode, Galen Low sits down with Jim Iyoob (President of ETS Labs, CCO at Etech Global Services) and Manu Dwievedi (AVP at ETS Labs) to cut through the noise around large-scale AI transformation in customer experience. Together, they unpack what’s really happening in call centers worldwide, why AI is more about augmentation than replacement, and how organizations can implement AI without breaking the customer or employee experience.From pragmatic strategies to leadership-level insights, this conversation tackles the real challenges of AI change management: how to start small, get quick wins, and bring people along for the journey. Whether you’re leading a CX transformation or navigating an AI project in any industry, you’ll leave with concrete strategies to make AI work for your team instead of against them.Resources from this episode:Join DPM MembershipSubscribe to the newsletter to get our latest articles and podcastsConnect with Jim and Manu on LinkedInCheck out ETS Labs and Etech Global Services
The Digital Project Manager is the home of digital project management inspiration, how-to guides, tips, tricks, tools, funnies, and jobs. We provide project management guidance for the digital wild west where demanding stakeholders, tiny budgets and stupid deadlines reign supreme.
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