Ever wonder how things actually get done in a tech company? This week, John and Nate sit down with Jennifer Silvestre, Business Unit Operations Lead at insightsoftware, to decode the art of cross-functional alignment.

Jen shares her journey from market research to becoming a functional chief of staff (even if that's not her official title), and reveals the playbook for getting things done when you don't have direct authority. From "herding cats" across departments to knowing the "beats of the business," she breaks down what it really takes to turn organizational politics into productivity.

Lessons Learned: John worries about AI replacing product managers, Jenn reflects on work-life balance heading into Q4, and Nate discovers that Beethoven (the dog movie) has a deeply disturbing plot.

Jen's LinkedIn: https://www.linkedin.com/in/jennifersilvestre/

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

"One throat to choke." "Peek behind the kimono." "Let's go." You've heard them all, probably cringed, and maybe said a few yourself.

John ran an experiment: he analyzed earnings calls from the top 50 tech companies and found that buzzword usage spikes when performance tanks. Turns out corporate jargon is just expensive filler.

We go through our personal lists of phrases we'd retire, debate better alternatives, and admit which ones we're guilty of using. John hates "fly the plane while we build it." Nate makes the case against military jargon in software. And we discover that "puts and takes" might actually be useful.

Also: the difference between bison and buffalo, why crystallized knowledge matters more as you age, and John's continued quest to disconnect from his phone.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

What starts as "I need to practice presenting" can turn into a personal brand that opens doors. Ann Marie Chrudimsky, Enterprise Account Executive at Box, joins John and Nate to share how her Blue Microphone interview series evolved from Instagram book reviews to interviewing executives at her company's annual conference.

The conversation explores why some of the best side projects start with skill-building rather than ambition, how to navigate organizational politics when you want to create content, and why writing and project management are becoming more valuable as AI floods inboxes with generic messages. Ann Marie also breaks down the reality of enterprise sales cycles, navigating increasingly complex procurement processes, and how relationship-building remains the differentiator when everyone else is automating.

Plus: How AI may solve a decades old OCR challenge, why tech barriers stop more projects than fear does, the strategic advantage of starting with low-stakes personal content, and proof that John was once good at talking to customers.

Topics covered:

• Building skills through low-stakes practice
• Creating content that serves your development (not just your company)
• Navigating organizational support for personal brand initiatives
• Enterprise sales in an era of security scrutiny
• Why human touch matters more as automation increases

Lessons learned: Dead mice at school require parental conversations, 5.5 million devices still run Windows XP, and Best Buy now helps your grandma stay at home longer.

Find Ann Marie and the Blue Microphone series on LinkedIn: https://www.linkedin.com/in/annmariechrudimsky/

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

In tech, change is the only constant—new tools, new org structures, new mandates from leadership. But when AI is disrupting workflows, return-to-office debates are raging, and your role feels like it's being redefined every quarter, what can you actually count on?

In this episode, John and Nate dig into the fundamentals that remain valuable no matter what's changing around you. They explore the core skills and principles that will serve you well whether you're navigating AI adoption, shifting org priorities, or just trying to prove your worth when the ground keeps moving.

Key Topics:

• The timeless PM/PMM skills that outlast any trend (hint: curiosity is more powerful than you think)
• Why "staying in your lane" drives John absolutely nuts—and what that reveals about thriving in cross-functional roles
• How to demonstrate "4D chess" thinking in interviews and everyday work
• The difference between being data-driven by necessity vs. by nature
• Why fast iteration and reflective listening never go out of style

What You'll Learn:

• How to identify what's steady vs. what's shifting in your role
• Interview techniques that prove you can think beyond your immediate responsibilities
• The real definition of curiosity as a professional skill (and how to develop it)
• Why your technology toolkit changes but your core value proposition doesn't have to

Plus, Nate shares surprising research about drunk chimpanzees (yes, really), and John reveals why assaulting a referee is a federal offense. Because somehow these tangents always connect back to product management.

Whether you're trying to stay relevant in your current role or position yourself for what's next, this episode offers a framework for identifying—and doubling down on—the skills that will always matter.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

John and Nate dive into how organization size fundamentally changes what product managers and product marketers actually do day-to-day. From sub-100 person companies to 20,000 person enterprises, they explore the trade-offs between moving fast versus having massive impact, and whether small orgs are really as nimble as everyone thinks.

They discuss Gartner's recent stock troubles (down 50% this year), debate whether AI is killing research firms, and unpack the wild differences between having one PM per product versus teams of 10+ PMs working on a single offering. Plus: the unexpected value of specialization, why John prefers "creative mess," and Nate's surprise that Napster still exists.

Key topics:

• How PM/PMM responsibilities shift with company scale
• The specialist vs. generalist career question
• Resource allocation strategies for product teams
• Why defensible credibility still matters in the AI age

Gettin' to Market: For when your job is real, but your role is negotiable.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

Nate and John are joined by special guest, Kyrie Slater, Senior Director of Growth Marketing at insightsoftware. They explore how growth marketing fits into the organization, discuss the evolution of marketing roles in the age of AI, and debate whether B2B and B2C are really that different. Kyrie shares war stories about failed video experiments, the real truth about MQLs, and why building trust with sales is everything.

Stick around for Lessons Learned to hear about hair splinters, ICEEs, and Bad Guys 2.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

Are you a player or the grounds crew? Which do you prefer your manager to be? John and Nate dive into a LinkedIn post that divided them on what leadership actually means. John argues leaders should focus on building environments where people can succeed—you prep the field, not play the game. Nate pushes back, making the case for player-coaches who lead by example and can still do the work as well as anyone else.

The conversation gets personal as they explore what actually motivates people: Do you want a leader who sets perfect conditions for you to succeed, or one who can jump in and show you how it's done? From Pete Rose to Taylor Swift (yes, really), they unpack different leadership styles and what drives high performance.

Plus: John shares his "lethal when given space" philosophy, Nate reveals why seeing his mentor's messaging work still inspires him, and they both grapple with whether AI is making teams faster or just spinning gears that don't connect.

Whether you're managing people, being managed, or just trying to figure out what good leadership looks like in product roles, this episode will make you question what you actually want from the people above you—and what you should be giving the people below you.

Also featuring: Wisconsin music connections and power grid management as a surprisingly interesting career.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod

John and Nate flip the script from their earlier "features" episode to explore purchases driven purely by brand loyalty and reputation. From Nate's NASA-approved Omega Speedmaster to John's Sonos soundbar impulse buy, they examine when brand trumps functionality.

The hosts dig into the psychology behind brand-based purchasing decisions, debating whether Apple's ecosystem counts as "brand" or something else entirely. They explore examples ranging from gas station spectacles like Buc-ee's to premium knife purchases that didn't quite live up to expectations.

Key topics:

• The difference between buying for brand vs. ecosystem integration
• When brand purchases pay off (and when they don't)
• How manufacturing consolidation affects perceived brand differences
• Apple's ecosystem lock-in strategy across devices

Plus: Lessons learned about AI adoption hitting buyer's remorse phase, the hidden world of Taiwanese bike manufacturing, and why John owns two identical band saws.

New Episodes every Tuesday

Videos and clips available on YouTube: https://www.youtube.com/@GettintoMarketPod