Connect To Market

Connect To Market

A movement of B2B marketers who realize direct connection with buyers is the foundation of all growth.

Episodes

October 22, 2026 • 46 mins

In a world where marketers are increasingly guided by data and AI, how do you make sure you're still connecting with the human on the other side of the glass?

In this episode of Connect To Market, host Casey Cheshire sits down with David Stark, CMO of Openstream.ai, to explore why human connection remains at the heart of effective marketing, even in an increasingly data-driven, AI-powered world. David argues that marketers can get s...

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Why do you actually want to connect to your market?

In this episode of Connect To Market, host Casey Cheshire sits down with Suresh Balasubramanian,CMO at Qualio, to explore why the first step in connecting to your market has nothing to do with tools. Suresh argues that marketers have more signals and listening technology than ever, which makes it harder to tell real insight from noise. His answer is to go back to first principles a...

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What happens when your marketing, sales, HR, and leadership teams aren't all telling the same story?

In this episode of Connect To Market, host Casey Cheshire sits down with Justin Brady, founder of Cultivate and a PR, communications, and GTM strategist, to explore why internal alignment is the foundation for connecting with your market. Justin argues that before companies worry about campaigns, content, PR, or demand genera...

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How can marketers use improv, human connection, and a market-led mindset to better understand their customers?

In this episode of Connect To Market, host Casey Cheshire welcomes Danielle Radden, CMO at Magic Door, to explore why the best way to connect with your market may be to stop assuming you already know what your customers want. Danielle shares her unconventional approach to marketing through the lens of improv, where being op...

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Is your brand sounding exactly like everyone else's because AI made "being everywhere" too easy?

In this episode of Connect To Market, host Casey Cheshire sits down with Brett Van Buskirk, VP of Marketing at TrueML, to explore how marketers can connect to their market by staying human and accessible instead of hiding behind the same AI-polished, on-brand talking points as everyone else. Brett argues that AI has erased the old distri...

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Is your product marketing drowning in features your customers never asked for?

In this episode of Connect To Market, host Casey Cheshire sits down with Beth Barach, VP of Product Marketing at Brinqa and a cybersecurity marketing leader, to explore how marketers can connect to their market by escaping the "inside-out" trap of messaging that leads with features instead of customer problems. Beth explains why this trap persists: engine...

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Digital outreach couldn't get a meeting with these prospects. A tech-enabled water bottle and a handwritten note did.

In this episode of Connect To Market, host Casey Cheshire sits down with Amy Sitnick, VP of Marketing at Viedoc, to talk about what it actually means to bring humanity back into B2B marketing. Amy makes the case that knowing your buyers, your clients, your internal stakeholders, and even the influencers writing about...

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What if the fastest way to master nine marketing verticals isn't a better dashboard, but getting your team out from behind their desks?

In this episode of Connect To Market, host Casey Cheshire sits down with Elyssa Steiner, CMO of Kahua, to explore how B2B marketing leaders can build stronger buyer connection through a mix of field research and AI-driven execution. Elyssa makes the case that AI can scale what you already know, but ...

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What does it take to build authentic communities that truly connect with your market?

In this episode of Connect to Market, host Casey Cheshire welcomes Paul Jones, Moderator of the Connect To Market Community & Founder of Bridgio. Paul shares lessons from building over 40 successful communities and explains why real market connection goes beyond launching products or campaigns.

He emphasizes the importance of deeply understandin...

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What happens when you take a podcast out of the studio and bring it into the middle of a live event?

In this special edition of Connect To Market, host Casey Cheshire joins us live from Las Vegas and the Ringmaster Mobile Podcast Studio at Black Hat to share why live events and podcasts can be such a powerful combination for B2B marketers. In between recordings, Casey breaks down how brands can use podcasting to create more human co...

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How can marketers harness AI to boost productivity and innovation without losing the human expertise that drives real results?

In this episode of Connect To Market, host Casey Cheshire welcomes Keven Ellison, Vice President of Marketing at A.I.S., to explore how AI is transforming marketing, content creation, and business systems while still honoring the experience and strategy that drive real results. Keven discusses the rapid adva...

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What if the reason marketing keeps getting sidelined is because marketers are measuring the wrong things?

In this episode of Connect To Market, host Casey Cheshire sits down with Randy Brasche, Chief Revenue Officer at Spot-On, Principal at Adaptive B2B Solutions, and author of "Some Assembly Required," to explore how marketers can connect to their market by getting close to revenue rather than hiding behind conversions and volume m...

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What if the biggest threat to your podcast isn't your audience, but the people inside your own company?

In this episode of Connect To Market, host Casey Cheshire sits down with Ryan Becker, Founder of Intuitive Podcasting, to explore how marketers can connect to their market by treating internal stakeholders as a primary audience and approaching their podcast like a true product. Ryan makes the case that executives, bosses, and clie...

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Is your brand losing deals because you sound exactly like every other vendor in the market?

In this episode of Connect To Market, host Casey Cheshire sits down with Karl Van den Bergh, Chief Market Officer of Illumio, to explore how marketers can connect to their market by knowing who they are and leading with authenticity in a noisy, AI-saturated landscape. Karl makes the case that the number-one requirement for market connection i...

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Are your trade show leads filling your CRM but starving your pipeline?

In this episode of Connect To Market, host Casey Cheshire sits down with Melanie Brancaleone, Vice President of Marketing at Testkube, to explore how marketers can connect to their market by getting in-person at events, where direct conversations reveal real language, context, and problems that forms and digital channels simply cannot capture. Brancaleone makes t...

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Are your buyers building shortlists with AI before they ever talk to your sales team?

In this episode of Connect To Market, host Casey Cheshire sits down with Melissa Beck, VP of Corporate Marketing at Sumo Logic, to explore how marketers can connect to their market by staying "relentlessly close" to the buyer journey as AI reshapes how prospects discover, research, and decide. Beck makes the case that buyers increasingly use AI too...

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What if the key to better marketing isn't more automation but more empathy?

In this episode of Connect To Market, host Casey Cheshire welcomes Anne Murlowski, VP of Marketing at Claravine and Host of the SaaSy podcast, to explore how marketers can connect to their market by focusing on individuals, not just companies or personas. Anne makes the case that in an AI-driven "do more with less" environment, the most effective messaging t...

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What happens when AI can replicate your marketing overnight, and your competitors sound exactly like you?

In this episode of Connect To Market, host Casey Cheshire sits down with Tim Hillison, Founder and Chief Marketing Officer of Entry Point 1, to explore how companies can connect to their market by building defensible advantage as AI accelerates output and risks turning every brand into a commodity. Hillison argues that the smart...

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Is your cybersecurity marketing failing because you're trying to say too much to too many people?


In this episode of Connect To Market, host Casey Cheshire sits down with Phill Keaney-Bolland, Co-Founder of Yaya and a brand and design strategist specializing in cybersecurity, to explore how marketers can connect to their market by doing less and getting radically clearer on the fundamentals. Phill argues there is no single hack ...

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What if the AI answers your buyers trust are already ignoring your brand?


In this episode of Connect To Market, host Casey Cheshire sits down with Simon Wilhelm, Co-Founder of SCAILE Technologies to explore how companies can connect to their market by showing up where buyers are actually looking: inside the answers generated by ChatGPT, Perplexity, and Google AI Overviews. Wilhelm's core thesis is counterintuitive: to win with A...

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