The Digital Project Manager

Latest Episodes:

How to Know If Your Team’s Ready for AI in PM Software Sep 30, 2025

Show notes

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 Membership
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Connect with Olivia on LinkedIn
Check out Capterra
Olivia’s report, AI & Security Are Top Concerns in Capterra’s 2025 Project Management Software Trends Survey

How to Start a PM Career When Generative AI is Replacing Entry-Level Roles Sep 23, 2025

Show notes

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 Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Ben on LinkedIn
Check out CLYMB Consulting

Turning AI Experiments Into Agency Impact: Transforming Curiosity Into Measurable Results Sep 18, 2025

Show notes

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 Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Melissa, Kelly, Harv on LinkedIn
Check out Agency Authority, VML, Scoro and The Handbook: Agency Ops podcast

How AI Leadership Shapes Project Delivery (and When You Need It) Sep 11, 2025

Show notes

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.

Why Automating Everything is The Wrong Move (And What to do Instead) Sep 04, 2025

Show notes

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 Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Jim and Manu on LinkedIn
Check out ETS Labs and Etech Global Services

Are You Tracking the Wrong Metrics? How AI Can De-Risk Delivery Aug 27, 2025

Show notes

How do you know if you’re tracking the right project metrics—or if you’ve been chasing the wrong numbers all along? In this episode, Galen sits down with Lior Gerson, Co-founder & CEO of TargetBoard.ai, to unpack how AI is reshaping KPI management and why aligning metrics with business strategy is the real game-changer.

Together, they explore how project leaders can move beyond legacy metrics like velocity and utilization to focus on measures that truly drive impact. From tackling cultural mismatches around KPIs, to building real-time forecasting models, to leveraging AI for smarter, faster reporting—this is a conversation about cutting through the noise and making metrics meaningful.

Resources from this episode:

Join DPM Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Lior on LinkedIn
Check out TargetBoard.ai
When the Old, and the New Metrics Fail – Jim Highsmith

Beyond the Billable Hour: How AI Is Making Time & Materials Irrelevant Aug 14, 2025

Show notes

In this episode, Galen Low sits down with Brian Kessman of Lodestar Agency Consulting to tackle a big question: is AI finally the deathblow to billable hours? Brian argues yes—and not because AI “broke” the model, but because it’s exposed just how misaligned hourly billing has always been with the real value agencies deliver. Instead of rewarding efficiency and innovation, time-based pricing incentivizes dragging things out and commoditizes expertise. The real shift, Brian says, isn’t just about swapping billing methods—it’s about fundamentally rethinking what you sell, how you position it, and how you prove its impact.

They dig into the Agency Value Model—a framework for moving from selling time to selling outcomes. Brian explains how to define your best-fit clients, identify their high-value problems, and design structured solutions that command higher prices while delivering measurable impact. Along the way, they unpack how to navigate the “race to the bottom” fueled by AI, nearshoring, and automation; why confidence in your positioning can help you turn away misaligned clients; and how to operationalize repeatable, scalable value delivery without falling back into chaos.

Resources from this episode:

Join DPM Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Brian on LinkedIn
Check out Lodestar Agency Consulting
Value Model Assessment
Agencies building business models around AI offerings:
- Go Supergood — an AI-native creative agency
- Silverside.ai — an AI innovation lab
- Skeptic™ by Known — uses machine learning and artificial intelligence to deploy rapid scientific experimentation and persistent optimization
- Jellyfish — social media AI agents
- Magnolia by Newfangled — is an AI-powered strategic planner
- Content Symphony

How Can We Lead Creative Projects Now That AI Has Entered The Chat? Aug 05, 2025

Show notes

AI is transforming the creative workflow—but not in the ways we first expected. In this conversation with Galen Low, creative and PM leaders Sara Fisher, Sara Doubleday, and Greg Storey talk through the practical and philosophical implications of AI’s growing role in creative work. This isn’t about flashy tools or end-to-end automation. It’s about realigning how teams work, communicate value, and preserve the human essence in their process.

From misinformed client expectations to the strategic reframing of creative outputs, the panel explores how project leaders and creatives can use AI to amplify their strengths rather than replace them. Spoiler: there’s still no shortcut for trust, authenticity, or thoughtful strategy.

Resources from this episode:

Join DPM Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Sara Fisher, Sara Doubleday, and Greg Storey on LinkedIn
Check out Vye and Seer Interactive
Check out Greg’s book – “Creative Intelligence: Don’t Ask AI, Think With AI”

The Retro: Designing Your PM Career for More Pay and Purpose Jul 24, 2025

Show notes

Navigating a career in project management today means wrestling with more than just Gantt charts and stakeholder standups—it means making high-stakes decisions about your salary, your specialization, and what brings you meaning at work. In this panel episode, Kelsey Alpaio brings together PM thought leaders Ben Chan, Mackenzie Dysart, and Elizabeth Harrin for a candid conversation on how to design your PM career with both pay and purpose in mind.

Together, they unpack fresh data from DPM’s 2025 Salary Guide and tackle some of the most pressing questions PMs are facing right now: Should you specialize or stay a generalist? When do certifications actually help? Is it ever too late to take control of your career? And how do you make confident moves when AI and automation are reshaping the role in real time? This is a jam-packed episode full of tactical tools, honest reflections, and grounded advice for anyone looking to take the reins of their project career.

Resources from this episode:

Join DPM Membership
Subscribe to the newsletter to get our latest articles and podcasts
Connect with Ben, Mackenzie, and Elizabeth on LinkedIn
Check out Thoughtworks and Rebel’s Guide to Project Management
Organized Chaos Café – Ben’s podcast
Managing Multiple Projects – Elizabeth’s book

The Retro: How to Negotiate a Raise as a PM (And Actually Get It) Jul 15, 2025

Show notes

When it comes to getting paid what you’re worth, project managers in 2025 are facing a unique challenge: job switching no longer guarantees a big raise, and most PMs are staying put—even if they feel underpaid. So what now? In this episode, Kelsey Alpaio sits down with Mukhtar Kadiri, Pam Butkowski, and Elaina Martinez to talk real strategies for negotiating a raise where you are—with confidence, clarity, and without burning bridges.

You’ll hear honest takes on why PMs feel undercompensated, how the market has shifted, and what leaders actually want to hear in raise conversations. From mapping your invisible impact to understanding company timing cycles and navigating tough “no’s,” this panel brings practical, actionable insights for anyone ready to make the ask—and get results.

Resources from this episode: