Event ROI for Early-Stage Startups: Lessons Learned the Hard Way

Product Management in the Age of AI: Master It or Get Left Behind

Product management is the connective tissue between company strategy, customer insight, engineering, and go-to-market. From early-stage startups trying to find product-market fit to scaling enterprises managing complex portfolios, the PM is the role most responsible for ensuring the right things get built for the right reasons and are brought to market effectively. But the role is being disrupted. AI is accelerating engineering velocity, adding pressure for PMs to move faster on customer research and discovery, and creating new expectations from boards, investors, and leadership about how product teams should operate. The PM's job hasn't gotten smaller, but it's getting more complex and urgent. In this episode, Rob sits down with Chris Mann, Founder of GrokAI and a seasoned product leader with experience at LinkedIn, 1Password, You.com [http://You.com], and Bizo, to discuss why product managers must embrace and innovate with AI every day, and figure out how to smartly apply it when aligning product strategy with company objectives, driving inbound research and customer discovery, and working cross-functionally with engineering, sales, and marketing to activate and launch. If you're in product management, product marketing, or leading GTM strategy, this episode is a grounded look at what it means to be a high-impact product leader today in the face of AI transformation.

The Trust Gap: Why Most B2B Brands Play It Safe, and Lose

In B2B marketing, everyone talks about differentiation, bold storytelling, and building memorable brands. Yet scroll through your LinkedIn feed, and it’s hard to tell one company from another. In this episode, Rob sits down with Skott Bennett, Senior Director of Brand at Qlik, to unpack what may be the most overlooked constraint in modern go-to-market strategy: trust. Not trust in data or dashboards, but trust in people. Specifically, the willingness of leaders to empower experienced brand and creative teams to take risks, make bold decisions, and stand out. The conversation explores the narrative tension between brand and product marketing, the fatigue with the “measure everything” era, and why an overreliance on metrics may be driving B2B marketing toward a sea of sameness. If you're a CMO, founder, or go-to-market leader trying to break out of safe, forgettable marketing, this episode is a candid look at what it takes to build a stand-out brand.

Beyond Translation: What International Expansion Really Demands of Marketing

No matter what country your B2B business is based in, there will come a time in your growth journey when you must evaluate regional or even global expansion as part of your go-to-market strategy. In this episode, Rob speaks with Angela Troccoli, head of marketing at Revecore, who shares real-world insights from her experience as an American marketing leader working for companies headquartered outside the U.S. and helping organizations expand across borders in both directions. Angela explores the cultural and organizational challenges of international marketing, from being expected to unlock the U.S. market to translating strategy, expectations, and execution across global teams. She explains why international expansion is never just about translating content. It’s a full cultural and operational shift that requires the right marketing foundation, investment, and leadership alignment.

Event ROI for Early-Stage Startups: Lessons Learned the Hard Way

There's no single right way to do events. But after three years of experimenting with conferences, dinners, and online community gatherings, Philippe Boutrous has found plenty of wrong ones. In this episode, Rob sits down with Philippe, cofounder of GetWhys, to get candid about what early-stage startups get wrong when they bet on events as a growth channel - from expensive conference sponsorships that go nowhere to in-person dinners that miss the mark. The conversation gets practical fast: whether to sponsor or skip major conferences, how to design events that generate real pipeline, who to bring from your team & who to leave at home, and why online community events are more valuable than most founders think. If you're a founder or early-stage marketing leader trying to figure out where events fit in your go-to-market, this episode will save you time, money, and at least a few awkward dinners.

Leveraging AI to scale marketing from 0 to 1

AI is rapidly changing how marketing teams are built, but scaling from zero to one still requires judgment, creativity, and human leadership. In this episode, Rob speaks with Jakki Geiger to explore how she is using AI as a force multiplier across the earliest stages of building a modern B2B marketing organization, from brand and messaging to demand, competitive intelligence, and thought leadership. The conversation looks at practical ways Jakki and her team are using AI to synthesize voice-of-customer insights, sharpen ICPs and positioning, support distinct executive POVs, and augment SDR capacity - while keeping humans firmly in the loop. Rather than chasing an “AI-first” mandate, it’s all about an AI-forward opportunity: designing lean teams where AI and people work together to move faster, learn quicker, and scale impact without replacing the roles that matter most.