Connect To Market

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...

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...

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" environ...

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 commo...

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...

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...

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...

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 ea...

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 engin...

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...

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 thei...

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...

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 mus...

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...

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 in...

How can B2B SaaS companies build a strong go-to-market foundation and turn their website into a true driver of pipeline? In this episode of Connect To Market, host Casey Cheshire welcomes Ian Dowe, Senior Vice President Marketing at HealthAxis, to explore how marketers can connect to their market through a deeply data-driven foundation. Ian explains why understanding your total addressable market,...

How can booth design and messaging transform your trade show results? In this special episode of Connect To Market, I sat down with Bill Kenney, Founder & Client Advocate of MEET. Bill brings his wealth of knowledge on booth strategy and lead generation, offering practical insights that help businesses turn trade show floors into high-performing sales opportunities. Bill breaks down why tradit...

How can marketers better connect with their market when customer insights are often filtered, polished, or stuck in silos? In this episode of Connect To Market, host Casey Cheshire welcomes B2B GTM Leader Angela Earl to explore how organizations can strengthen their connection to customers by listening more closely- not just to feedback, but to the real conversations happening across their teams....

How can B2B brands win discovery, trust, and positioning when most cybersecurity messaging blends together? In this episode of Connect To Market , host Casey Cheshire welcomes Valerie Zargarpur, Head of Marketing at Monad, to explore how marketers can connect to their market through brand story rather than just visual identity. Valerie explains why B2B, especially cybersecurity, often relies on ja...

How can marketers escape the tactics trap and build category strategy that actually connects to the market? In this episode of Connect To Market, host Casey Cheshire welcomes John Rougeux, Founder of Flag & Frontier, to unpack why marketers are often set up for failure when they’re handed KPIs without influence over strategy. John argues that real market connection starts with understanding th...

How can challenger brands win discovery, trust, and positioning as generative AI reshapes how buyers find and evaluate solutions? In this episode of Connect To Market, host Casey Cheshire welcomes Valerie Riley, Vice President of Marketing & Strategy at Unbounce and Co-Host of the Closing Time podcast, to explore how generative engine optimization (GEO) is transforming modern marketing. Valeri...

How can mastering MarTech unlock customer connection and marketing success in the age of AI? In this episode of Connect To Market , host Casey Cheshire welcomes Scott Brinker, Martech Analyst and Advisor at ChiefMartec, to explore how marketing is evolving in a technology-driven world. Scott shares how prioritizing direct customer engagement, maintaining brand integrity, and delivering exceptional...

How can marketers build stronger connections by truly listening to their customers? In this episode of Connect To Market, host Casey Cheshire sits down with Emily Ward, Vice President of Marketing at Maxwell, to explore why direct customer conversations are still one of the most powerful tools in a marketer’s toolkit. Emily shares how common obstacles like egocentric thinking, fear of honest feedb...

How can strategic storytelling help marketers stand out in an AI-driven world? In this episode of Connect To Market, host Casey Cheshire sits down with Tim Lozier, Owner of Big Breakthrough Marketing, to explore how shifting the focus from company-centric messaging to the buyer’s story creates clearer, more effective marketing. Tim shares why the most impactful content starts with understanding th...

How can mastering market messaging   unlock founder-led growth in B2B SaaS? In this episode of Connect To Market, host Casey Cheshire welcomes Chris Silvestri, Founder & Chief Conversion Copywriter at Conversion Alchemy, to unpack how achieving message-market fit can transform B2B marketing effectiveness. Chris shares how deeply understanding your market through research, internal team alignme...