The Digital Project Manager

Finding the right freelance project manager can feel like searching for a unicorn. Do you hire someone who knows your industry inside out, or someone who can solve the problem in front of you? And if you're a freelance PM looking to branch into a new industry, how do you know which of your skills will actually transfer?
In this episode, host Galen Low sits down with Ashanti Johnson, founder of the Freelance PM Club and owner of Strategy House, to unpack what makes a great freelancer-client match. They explore why industry experience isn't always the deciding factor, how to position your expertise around outcomes rather than job titles, and why the future of freelance project management depends on treating independent professionals as strategic partners, not just extra hands.
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AI is changing how software gets built, but does that mean technical program managers (TPMs) and engineering managers should become one role? Not so fast. As engineering teams move faster with AI, the need to manage dependencies, anticipate risks, and keep cross-functional teams aligned isn't disappearing. It's evolving.
In this episode, host Galen Low sits down with Satish Menon, a technical program management and engineering operations leader with experience at Google, Dell, and other major software companies. Together, they explore what technical fluency really means for TPMs, how AI is shifting the value of program management, and why the future of the role depends less on tracking work and more on solving problems, earning trust, and orchestrating delivery at scale.
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AI search is changing discovery, but the playbook isn’t about finding a magic prompt, tag, or shortcut. Matt Slater, founder of Receipts, explains why AEO and GEO still depend on fundamentals: knowing who your brand is for, publishing clear first-party information, and building enough real-world credibility for third-party sources to corroborate what you say about yourself.
For project professionals, that shift matters. Stakeholders may want immediate visibility in ChatGPT or Claude, but sustainable results come from consistent, integrated work across brand, content, reputation, and search—not hacks that could disappear with the next update. And as zero-click searches grow, success may increasingly look less like “more traffic” and more like better-informed prospects arriving ready to act.
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AI’s biggest opportunity in professional services may not be replacing expertise—it’s removing the operational drag that keeps experts from using it. In this conversation, Projectworks CEO Mark Orttung explores how AI can take on the neglected or repetitive work around proposals, resource planning, timesheets, invoicing, and forecasting while keeping human judgment firmly in the loop.
The bigger shift is moving beyond using AI for isolated tasks and rethinking entire business processes around it. For consulting firms, that means connecting the journey from winning work to staffing it, delivering it profitably, and getting paid—with better data and fewer administrative handoffs along the way.
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Strategic initiatives rarely stall because teams aren’t working hard enough. More often, the information leaders need to make timely decisions is scattered across Jira, Asana, Slack, spreadsheets, meetings, and everything in between. By the time a risk becomes visible at the executive level, the opportunity to address it early may already be gone.
Galen Low sits down with Maria Delgado Oliveros, founder of glidiffy and former program management leader at Uber, Hexagon PPM, and Chime, to unpack what makes strategic initiatives different from ordinary projects—and why better visibility can transform the relationship between program managers and executive sponsors. They explore how PMs can spend less time chasing updates and more time understanding dependencies, surfacing risks, making trade-offs, and becoming trusted operational partners.
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