Connect To Market

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...

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...

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...

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...

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...

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...

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...

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...

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 ...

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...

What if the "average customer" your marketing targets doesn't actually exist?

In this episode of Connect To Market, host Casey Cheshire sits down with Eric Robertson, Head of Partnerships & Sales at Theta, to explore why building marketing strategies around average customer personas and demographic trivia leads teams to waste budget on the wrong people. Robertson makes the case that customers vary dramatically in value, followin...

If everyone is using AI to create content, what actually makes your brand stand out?

In this episode of Connect To Market, host Casey Cheshire sits down with George Smith, Community Engagement Manager at Rewst, to explore how marketers can connect to their market by doubling down on what AI cannot replicate: genuine human connection. Smith argues that as AI-generated content becomes noisier and easier to spot, the competitive advant...

Does AI make every brand sound exactly the same?

In this episode of Connect To Market, host Casey Cheshire sits down with Brian C. Reed, Chief Market Officer at Corsha and veteran B2B tech marketing executive, to explore why marketers who lean on AI for differentiation are actually flattening their messaging into sameness, and how authentic, human storytelling rooted in community is the real engine for memorability and brand prefere...

What if the real threat to your marketing isn't falling behind on AI, but not having the systems to use it?

In this episode of Connect To Market, host Casey Cheshire sits down with David Kosloski, VP of Marketing at SNUC and host of the Edge Tech Podcast, to explore how marketers connect to their market by building experience, expertise, authority, and trust before chasing tools or tactics. David makes the case that in emerging ...

What if your biggest competitor isn't another vendor, but your buyer's fear of making the wrong decision?

In this episode of Connect To Market, host Casey Cheshire sits down with Aaron Bean, Co-Founder and Head of Go-to-Market at Supercase.ai, to explore why the most dangerous competitor in B2B isn't a rival product, but buyer indecision. Aaron makes the case that marketers need to connect to their market by focusing on the late-sta...

Is your marketing falling flat because you don't actually believe in what you're selling?

In this episode of Connect To Market, host Casey Cheshire sits down with Brandon Pittser, VP of Marketing and Funding Development at Filament Games, to explore how marketers can connect to their market by leading with authenticity instead of automation. Brandon makes the case that the most effective marketing starts with genuinely believing in ...

How can marketers stay adaptable, leverage AI effectively, and earn a true seat at the table?

In this episode of Connect To Market, host Casey Cheshire welcomes Max Maurier, VP of Marketing at Absolute Security, to explore why adaptability is the most critical skill for modern marketing teams. Max shares how marketing is uniquely positioned to pivot faster than other functions, and why leaders must continuously evolve their stra...

What if the fastest way to improve your marketing performance isn’t better messaging but better data?

In this episode of Connect To Market, host Casey Cheshire welcomes Alex Schutte, Senior Vice President of Marketing at Hubstaff, to explore how marketers can connect to their market by prioritizing data clarity before refining messaging. Alex explains why many B2B teams struggle with alignment and trust due to inconsistent...

What if your most powerful growth strategy isn’t reaching more people, but starting with the ones closest to you?

In this episode of Connect To Market, host Casey Cheshire welcomes Melissa Moody, Founder of Wednesday Women and Host of the Joy of Connecting podcast, to explore how brands can drive growth by returning to authentic human relationships. Melissa introduces her “concentric circles of influence” framework...