Casey Cheshire

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 the category, buyer environment, and problem maturity - not chasing isolated tactics. Using a race car analogy, he explains why fundamentals matter more than surface-level optimization and how marketing becomes powerful when it shapes direction, not just execution.John outlines three core pillars: first, aligning on the real problem and who it’s for by talking directly to customers; second, assessing the maturity of that problem to determine whether to create a category, carve out a niche in a mature market, or reinforce leadership like Salesforce; and third, distilling strategy into a clear narrative that aligns internal teams and guides external messaging. Drawing a parallel to a trial lawyer’s structured argument, he explains how strong strategy blends logic and emotion to move markets. He also shares lessons from his path from finance to performance marketing to advising companies at strategic inflection points, including examples like how Zoom reinvigorated a crowded space.In this episode, we cover:Why marketers get trapped in tactics without strategic influenceHow to define the right problem through customer conversationsHow category maturity shapes whether you evangelize, niche down, or leadWhy strategy must be distilled into a narrative that aligns teams and drives growthIf you’re a marketing leader navigating crowded markets, executive misalignment, or a major inflection point, John’s framework offers a practical roadmap for moving from activity to alignment and from tactics to true category strategy.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with John:LinkedIn: https://www.linkedin.com/in/johnbrougeux/  Flag and Frontier: flagandfrontier.com  Substack: https://substack.com/@johnrougeux Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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. Valerie explains why GEO is emerging as a defining 2026 trend and how it shifts discovery from traditional search rankings to AI-generated recommendations. She shares why this shift can favor focused challenger brands over large incumbents that have historically dominated through budget and content scale.She breaks down how marketers can move from buying attention to earning understanding by sharpening positioning, embracing specificity, and creating content that educates rather than shouts. From building credibility through transparent comparisons to activating authentic B2B influencer relationships, Valerie outlines practical ways to increase trust and relevance in AI-driven discovery. She also reflects on internal AI adoption, top-down leadership support, and the discipline required to focus strategy when resources are limited. In this episode, we cover:Why GEO is reshaping discovery and favoring challenger brandsHow specificity and niche positioning improve AI visibilityPractical strategies for trust-building through education and comparisonsThe role of influencer marketing and internal AI adoption in accelerating growth If you’re a marketing leader looking to compete in an AI-powered landscape while building deeper market trust, Valerie’s approach offers a clear roadmap for sharpening positioning, increasing credibility, and winning in generative search.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Valerie:LinkedIn: https://www.linkedin.com/in/valerie-riley-marketer/  Unbounce: https://unbounce.com/  Closing Time Podcast: https://www.insightly.com/closing-time/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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 experiences provides a foundation for more effective, human-centered marketing.He explores how AI is reshaping consumer behavior, why traditional marketing principles remain important, and how marketing leaders can balance technology with human connection. From leveraging customer advocacy to ethical considerations in algorithmic pricing, Scott breaks down actionable strategies for creating loyal audiences, building trust, and driving meaningful impact. He also reflects on his journey in MarTech and how it informs his approach to marketing leadership.In this episode, we cover:Why customer interaction is essential for modern marketingHow AI is transforming marketing strategies and consumer expectationsPractical strategies for fostering customer loyalty and advocacyEthical considerations in AI-driven marketing and algorithmic pricingIf you’re a marketing leader looking to thrive in a fast-paced digital landscape while keeping human connection at the center, Scott’s approach offers a clear roadmap for building more strategic, customer-focused, and impactful marketing.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Scott:LinkedIn: https://www.linkedin.com/in/sjbrinker/Chief Martec: chiefmartec.comWays to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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 feedback, and internal gatekeeping can prevent teams from deeply understanding their audience and how to break through them.She unpacks practical ways to get closer to customers, from partnering with customer success teams to leveraging events, outreach, and qualitative feedback to uncover real pain points. Emily also reflects on her marketing origin story, the importance of differentiating yourself in a crowded market, and how emerging technologies like AI are reshaping SEO, inbound tracking, and the future of marketing. Throughout the conversation, she offers grounded advice for leaders who want to adapt, learn faster, and continuously refine their strategies based on what customers actually need.In this episode, we cover:Why talking directly to customers is essential for effective marketingHow to overcome internal gatekeeping and fear of customer feedbackPractical methods for uncovering deeper customer pain pointsHow AI and emerging technologies are influencing modern marketing strategiesIf you’re a marketing leader looking to build more authentic connections and create strategies rooted in real customer insight, Emily’s perspective offers clear, actionable guidance for staying relevant and effective in an evolving landscape.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Emily:LinkedIn: https://www.linkedin.com/in/emily-ward-marketing-vp/ Maxwell: https://himaxwell.com/ TikTok: https://tiktok.com/@emilyward011  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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 the real questions buyers are asking- and how AI can be used as a tool to surface those insights, not replace human judgment.He breaks down the role of long-form, evergreen content in building trust and authority, alongside the importance of short, digestible formats that meet audiences where they are. From prioritizing clarity over jargon and frameworks over features to encouraging a culture of smart experimentation, Tim offers practical guidance for modern marketing leaders navigating an increasingly noisy landscape. He also reflects on his own path into marketing and the lessons that shaped his leadership philosophy.In this episode, we cover:Why telling the buyer’s story is more powerful than promoting the companyHow AI can help uncover the questions buyers are truly askingThe role of long-form, evergreen content alongside short, digestible formatsWhy clarity, frameworks, and authentic helpfulness drive standout marketingIf you’re a marketing leader looking to create content that cuts through the noise and truly serves your audience, Tim’s insights provide a thoughtful framework for building trust, relevance, and impact in today’s AI-driven discovery world.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Tim:LinkedIn: https://www.linkedin.com/in/timlozier/  Big Breakthrough: https://big-breakthrough.com/  TOTData: https://www.totdata.com/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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 alignment, and competitive analysis creates a strong foundation for smarter strategy and more impactful messaging.  He explores why many marketing challenges stem from unclear positioning, and how asking the right questions, analyzing competitors, and understanding customer psychology brings clarity, focus, and stronger collaboration across teams. From balancing AI-assisted copywriting with human-driven creativity to refining messaging strategies based on market insights, Chris breaks down practical approaches for building differentiated, resonant market communication. He also discusses how his journey into copywriting and everyday experiences shaped his approach to marketing and leadership.In this episode, we cover:Why understanding your market is essential for effective messagingHow internal alignment and competitive analysis drive team successThe role of AI personas and human-driven copywriting in crafting messagingPractical steps to differentiate your offerings and refine your value propositionIf you’re a marketing leader or founder looking to connect more deeply with your market and customers, Chris’s approach offers a clear roadmap to building a more strategic, human-centered, and effective messaging strategy.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Chris:LinkedIn: https://www.linkedin.com/in/christophersilvestri/  Conversional Alchemy: https://conversionalchemy.net/ Message-Market Fit Podcast: https://christophersilvestri.com/podcast/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can deep market knowledge help your team win in B2B SaaS marketing?In this episode of Connect To Market, host Casey Cheshire welcomes David Schnepp, VP of Marketing at Virdee, to unpack how truly understanding your market can transform B2B marketing effectiveness. David shares how continuously learning about industry trends, listening to customer needs, and fostering company-wide expertise creates a strong foundation for smarter strategy and more impactful campaigns.He explores why many marketing challenges stem from a lack of market understanding, and how investing in learning, curiosity, and knowledge sharing brings clarity, focus, and stronger collaboration across teams. From innovative marketing strategies like direct mail to the importance of soft skills and emotional intelligence, David breaks down practical approaches for building a knowledgeable, adaptable, and successful team. He also discusses how everyday experiences, learning from failures, and company culture shape more effective leadership.In this episode, we cover:Why truly understanding your market is essential for effective marketingHow continuous learning and knowledge sharing drive team successThe value of curiosity, emotional intelligence, and soft skills in leadershipInnovative strategies and learning from everyday experiencesIf you’re a marketing leader looking to connect more deeply with your market and customers, David’s approach offers a clear roadmap to building a more strategic, human-centered, and knowledgeable marketing organization.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with David:LinkedIn: https://www.linkedin.com/in/davidschnepp/  Virdee: https://virdee.io/company/contact/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can marketers break old habits and innovate to create meaningful B2B buyer experiences?In this episode of Connect To Market, host Casey Cheshire sits down with Jennifer Cortez, Chief Marketing Officer of Alkami Technology, to explore how innovative marketing strategies can create real value and move beyond outdated practices. Jennifer shares her perspectives as a SaaS marketing expert, emphasizing the importance of personalized approaches, a culture of experimentation, and leveraging data and AI for smarter decision-making.Jennifer provides practical insights on rethinking traditional marketing tools, crafting content that resonates, and embracing the evolving buyer’s journey. She discusses the significance of mentorship, taking calculated risks, and fostering a marketing culture that continuously innovates. Through real-world examples, Jennifer highlights how leaders can create meaningful buyer experiences while staying ahead of the curve in an increasingly competitive market.In this episode, we cover:Why marketing the way you want to be marketed to leads to stronger buyer connectionsHow to balance personalization, content strategy, and data-driven decision-makingThe role of AI and innovation in shaping the future of B2B marketingWhy embracing change, mentorship, and risk-taking is critical for growthIf you’re a marketing leader looking to break away from “dinosaur” practices, elevate your strategies, and create experiences that truly engage buyers, Jennifer’s insights provide an actionable roadmap for modern marketing success.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Jennifer:LinkedIn: https://www.linkedin.com/in/jenniferncortez/  Alkami Technology: https://www.alkami.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

What does it take for marketers to truly connect with their audience and harness AI for impactful strategies?In this episode of Connect to Market, host Casey Cheshire welcomes Megan Ward, SVP of Marketing and Product Management at 360Factors. Megan offers a thoughtful and tactical breakdown of how marketers can deepen their understanding of target audiences by engaging directly and using AI-driven insights.She shares why marketing leaders must spend time with “real people” to uncover authentic needs, the importance of attending industry events for firsthand market observation, and how AI analysis of call recordings can reveal key customer questions and concerns. Megan also reflects on her career journey and the lessons that helped her overcome limiting beliefs.Throughout the conversation, Megan highlights actionable insights on connecting with customers, harnessing AI for smarter marketing, and documenting knowledge to empower teams.In this episode, we cover:The importance of engaging directly with your target marketUsing AI to analyze customer interactions and extract insightsThe future of AI in marketing: digital agents and personalized toolsThe critical role of documenting and sharing knowledge within teamsIf you're looking to build deeper market connections and integrate AI thoughtfully into your marketing, Megan’s insights provide a practical guide for leaders ready to innovate and lead with empathy.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Megan:LinkedIn: https://www.linkedin.com/in/radiantmegan/Substack: https://substack.com/@meganward989011 360factors: https://www.360factors.com/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

What happens when we slow down and lead with gratitude in a fast-moving, pressure-filled marketing world?In this special holiday episode of Connect To Market, host Casey Cheshire goes solo to reflect on the power of gratitude and why expressing it, openly and excessively, matters more than ever. Without a guest, Casey shares a heartfelt message of thanks to listeners, fellow marketers, and the team behind the show, creating space for presence, appreciation, and connection during the holiday season.Casey explores how gratitude can shift perspective, ease anxiety, and reduce fear and frustration, especially during moments of uncertainty or burnout. Drawing inspiration from voices like Jay Shetty, Robert Holden, and Gertrude Stein, he highlights how gratitude fosters abundance, peace, and a deeper sense of awareness in both work and life. This episode serves as a reminder that gratitude isn’t passive, it’s a practice that can transform how we show up for ourselves and others.In this episode, we cover:Why gratitude is a powerful tool for reducing anxiety and stressHow expressing appreciation creates presence, peace, and perspectiveQuotes and reflections that reframe gratitude as an active practiceWhy now is the perfect time to pause, reflect, and say thank youIf you’re closing out the year feeling stretched, reflective, or hopeful for what’s ahead, this episode offers a meaningful pause, and an invitation to carry gratitude with you into the new year.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Casey:LinkedIn: https://www.linkedin.com/in/caseycheshire/ Ringmaster: ringmaster.com Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

What does it really take to turn community into a powerful, long-term growth engine in an increasingly automated marketing world?In this episode of Connect To Market, host Casey Cheshire sits down with Sarah McNabb, Chief Marketing Officer at GigaStar, to explore how community-driven strategies fuel sustainable marketing growth, particularly within fintech and emerging technology spaces. Sarah reframes community not as a one-off tactic, but as a core business strategy rooted in trust, advocacy, and human connection.Sarah shares practical insights on defining community, building engaged and supportive spaces, and maintaining authenticity as AI becomes more embedded in marketing and customer experiences. She discusses the importance of empathy in customer interactions, managing communication overload, and how platforms like Discord are evolving to support diverse, purpose-driven communities. Through real-world examples, Sarah highlights how strong communities create resilience, deepen brand loyalty, and empower marketers to stay connected and informed.In this episode, we cover:Why community should be treated as a foundational marketing strategyHow authentic human engagement builds trust, loyalty, and advocacyThe role of empathy in customer experience and community leadershipHow to balance AI-driven efficiency with meaningful human interactionIf you’re a marketing leader looking to create deeper connections, strengthen brand resilience, and drive growth through community, Sarah’s insights offer a clear and actionable path forward.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Sarah:LinkedIn: https://www.linkedin.com/in/sarahmcnabb/   Twitter: https://x.com/SarahMcNabb2016 GigaStar: gigastar.io/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

What does it really take to build authentic, human-centered relationships in a B2B world driven by metrics and automation?In this episode of Connect To Market, host Casey Cheshire sits down with Beth Magee, VP of Marketing at GSI, to explore the power of authenticity in B2B marketing. Beth challenges the traditional view of buyers as transactions, emphasizing instead that buyers are people first. Drawing from her recent learning with the Arbinger Institute, she unpacks what it truly means to adopt a human-centric mindset in business.Beth shares practical strategies for building genuine connections, communicating with intention, and fostering deeper alignment between teams and clients. Through real-world examples and personal reflections, she explains how curiosity, empathy, and understanding personal context can reshape organizational culture and elevate professional relationships. Beth discusses how leaders can shift toward a more empathetic, people-first approach that strengthens both external partnerships and internal team dynamics.In this episode, we cover:Why treating buyers as people, not objects, drives stronger B2B relationshipsHow curiosity and personal context improve communication and trustPractical techniques for building genuine, lasting professional connectionsThe role of networking in growth, challenge, and long-term successIf you're a business or marketing leader looking to build more authentic, human-centered relationships that drive both connection and results, Beth’s insights will inspire a more empathetic and impactful approach to growth.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Beth:LinkedIn: https://www.linkedin.com/in/bethlmagee/  GSI, Inc: https://www.getgsi.com/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can purpose-driven marketing and AI-powered personalization transform the way brands connect with customers?In this episode of Connect To Market, host Casey Cheshire welcomes Andy Dé, Chief Marketing Officer at Lightbeam Health Solutions, to explore how understanding customer challenges and leading with value can turn marketers from vendors into trusted advisors. A three-time CMO and internationally recognized thought leader in AI for healthcare and life sciences, Andy shares how meaningful connection starts with truly listening to the customer.He dives into how AI can be leveraged for personalized outreach without crossing into invasiveness, and why value-based, consultative selling is essential in today’s digital-first world. Drawing from both his professional journey and personal experiences, Andy discusses how aligning marketing strategy with customer needs,  and a purpose bigger than oneself,  leads to deeper trust and stronger results. He also reflects on the evolution of marketing, continuous learning, and how finding your “why” shapes long-term success.In this episode, we cover:Why understanding customer challenges is the foundation of effective marketingHow to use AI for personalization without losing trustWhy value-based, consultative selling outperforms transactional marketingHow purpose, resilience, and continuous learning shape impactful leadershipIf you're a marketing leader looking to build stronger, more authentic customer relationships while responsibly leveraging AI, Andy’s insights will inspire a more meaningful, value-driven approach to growth.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Andy:LinkedIn: https://www.linkedin.com/in/andyde/  Personal Website: andyde.com Lightbeam Health Solutions: https://lightbeamhealth.com/   Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can a customer-first mindset and AI-driven insight transform founder-led growth?In this episode of Connect To Market, host Casey Cheshire welcomes Yogesh Mehra, Chief Marketing Officer at Neu, to dive into the power of connecting with customers more deeply than traditional marketing tactics often allow. Yogesh shares why many growth challenges are actually rooted in a lack of customer understanding, and how founders and marketing leaders can shift their focus to what really matters: the customer.He explores how qualitative and quantitative research, combined with clear customer personas, can create a foundation for better decisions and more effective campaigns. From uncovering untapped market opportunities to integrating AI as a tool to amplify, but not replace, human creativity, Yogesh provides a framework for aligning marketing strategy with real customer needs. He also discusses the evolving role of marketing leadership, the importance of curiosity and agility, and how focusing on customer-first approaches drives growth.In this episode, we cover:Why most growth challenges stem from a lack of customer insight, not tacticsHow to define and leverage customer personas to uncover new opportunitiesHow to use AI as an amplifier of strategy and creativity, not a substitute for human judgmentWhy modern marketing leadership starts with curiosity, feedback, and a customer-first mindsetIf you're a founder or marketing leader looking to build smarter, growth-oriented strategies rooted in real customer insight, Yogesh’s perspective will challenge your assumptions and elevate your thinking.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Yogesh:LinkedIn: https://www.linkedin.com/in/yogeshmehra/  Neu: https://neumoney.app/  Substack: yogeshmehra.com  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can marketers engage buyers earlier, create value through benchmarking, and build smarter strategies that drive real B2B results?In this episode of Connect To Market, host Casey Cheshire welcomes Michael Phelan, Principal and Founder at Go-to-Market Pros and a leading B2B marketing strategist, to explore how early buyer engagement and actionable benchmarking can transform the impact of modern marketing. Michael challenges the belief that buyers want to delay conversations and explains why engaging them early, when paired with real value, creates stronger momentum in the buying cycle. He shares how comparing performance against best-in-class competitors motivates action and helps marketing teams produce content that truly resonates.He also breaks down the power of running benchmarking studies, conducting moderated prospect meetings, and involving CMOs directly in conversations to uncover insights that shape long-term strategy. From leveraging community-driven learning to embracing AI tools, Michael highlights how marketers can elevate their programs by focusing on strategic alignment and real-world buyer understanding. He emphasizes that leaders must move beyond outdated models, stay close to their customers, and use early-stage engagement to strengthen decision-making and drive better outcomes.In this episode, we cover:Why early-stage buyer engagement leads to stronger conversations and better outcomesHow benchmarking creates insight-rich content and motivates buyers to take actionWhy moderated prospect meetings uncover game-changing strategic insightsHow communities and AI tools enhance modern B2B marketing strategyIf you’re a B2B marketing leader looking to drive deeper engagement, sharpen your strategy, and build programs rooted in real buyer insight, Michael’s perspective offers a practical and powerful guide to modern marketing success.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Michael:LinkedIn: https://www.linkedin.com/in/michaeljphelan1/ Go-To-Market Pros: http://www.gotomarketpros.com Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

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 advancements in AI and why being proficient in AI is essential for marketers to stay relevant. He shares his journey of learning to prompt effectively and building AI workflows that have drastically increased productivity. The opportunity lies in using AI to scale strategically while keeping messaging aligned with what truly matters to buyers.He shares why marketers must guide AI tools like a new team member by equipping them with brand knowledge, audience insights, and clear instructions to ensure quality and consistency. From building strong workflows to creating human feedback loops, Keven explains how marketers can accelerate content creation without sacrificing strategy or creativity. He also highlights the future of AI in organizations, predicting the transformation of traditional CRMs and human resource departments into AI-driven systems, and emphasizes the need for marketers to adopt and adapt to AI technologies to lead effectively.In this episode, we cover:Why marketers must stay ahead of AI trends to remain competitiveHow to master AI prompts and build scalable workflowsHow AI is changing the future of work, including CRM and HR systemsWhy human creativity and business experience remain essentialIf you’re a marketing leader looking to leverage AI while strengthening your strategy and creativity, Keven’s insights provide a smart, practical path to modern marketing success.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Keven:LinkedIn: https://www.linkedin.com/in/kevenellison  AIS-NOW: https://www.ais-now.com/ PromptMaster XL 1.2: https://chatgpt.com/g/g-682a348e1f7c8191a11cd42dda5f9ff3-promptmaster-xl-1-2 Image Prompt Architect: https://chatgpt.com/g/g-682bbe0333f48191aa6521a6cbf93958-image-prompt-architectWays to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can embracing AI elevate your marketing without losing the fundamentals?In this episode of Connect To Market, host Casey Cheshire welcomes Nick Talbert, VP of Growth & Marketing at BRIA.AI, to explore how AI can transform marketing execution while still honoring the core principles that drive real results. Nick discusses the paradox of automation and why technology doesn’t remove bottlenecks but simply moves them. The opportunity lies in using AI to scale strategically while keeping messaging aligned with what truly matters to buyers.He shares why marketers must train AI tools like a new team member by equipping them with brand voice, audience knowledge, and clear guidelines to ensure consistency and quality. From building the right messaging foundations to creating strong human feedback loops, Nick explains how marketers can use AI to accelerate content without sacrificing strategy or creativity. He also highlights the importance of curiosity, agility, and experimentation in staying competitive as marketing continues to evolve.In this episode, we cover:Why automation alone doesn’t fix marketing bottlenecksHow to train AI with brand knowledge and audience insightsWhy governance and human creativity are essential in AI workflowsHow curiosity drives more effective, innovative marketingIf you’re a marketing leader looking to adopt AI while strengthening your brand and strategy, Nick’s approach provides a smart, practical path to modern marketing success.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Nick:LinkedIn: https://www.linkedin.com/in/nick-talbert/  BRIA AI: https://bria.ai/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can mapping the buyer journey strengthen your market connection?In this episode of Connect To Market, host Casey Cheshire welcomes Cody Frew, VP of Marketing at CareCloud, to unpack how buyer journey mapping can transform B2B marketing strategy. Cody shares how clearly defining your ICP and buyer personas (and mapping their goals, actions, and questions across each stage) creates a powerful foundation for more effective, targeted campaigns.He explores why many marketing challenges stem from a lack of buyer understanding, and how mapping every touchpoint brings clarity, focus, and better collaboration across teams. From identifying content gaps to driving alignment between marketing and sales, Cody breaks down a practical framework for building maps that lead to real connection and measurable growth. He also discusses the evolving role of community in marketing, the rise of AI as a creative partner, and why curiosity remains a marketer’s most valuable skill.In this episode, we cover:Why mapping the buyer journey is key to improving engagement and conversionHow to define and apply your ICP and buyer personas effectivelyThe most common mistakes teams make when mapping and how to avoid themHow community and collaboration elevate your marketing impactIf you’re a marketing leader looking to connect more deeply with your market and customers, Cody’s approach offers a clear roadmap to more strategic, human-centered marketing.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Cody:LinkedIn: https://www.linkedin.com/in/codyafrew/   CareCloud: https://carecloud.com/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can prioritizing customer understanding reshape your B2B marketing approach?In this episode of Connect To Market, host Casey Cheshire welcomes Eric Bogard, Fractional Marketing Leader to High Growth Saas B2B, to dive into the power of understanding your users more deeply than traditional marketing tactics often allow. Eric shares why many marketing challenges are actually rooted in a lack of user insight, and how early-stage founders and marketers can shift their focus to what really matters: the customer.He explores how empathy, curiosity, and a strong grasp of ICPs can create a foundation for better decisions and more effective campaigns. From using Google Ads for fast feedback loops to integrating AI as a tool to amplify, not replace, marketers' skills, Eric provides a framework for aligning marketing with real user needs. He also discusses the evolving role of product marketing, the value of advisory boards, and how lifelong learning plays a key role in career growth.In this episode, we cover:Why most marketing problems are really understanding problems, not tactical onesHow to anchor every campaign to your ICP and balance quick wins with long-term discoveryHow to use AI as an amplifier of insight and empathy, not a substitute for themWhy modern marketing leadership starts with curiosity, feedback, and connectionIf you're a founder or marketing leader looking to build smarter strategies rooted in real customer insight, Eric’s perspective will challenge your assumptions and elevate your thinking.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Eric:LinkedIn: https://www.linkedin.com/in/ericbogard/  Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 

How can deep customer understanding drive more effective B2B marketing strategies?In this episode of Connect To Market, host Casey Cheshire welcomes Greg Perotto, VP of Global Marketing at Poggio to explore the power of deep customer understanding in shaping successful B2B go-to-market efforts. Greg emphasizes the critical need to move beyond surface-level personas and truly understand customer needs, priorities, and challenges to drive meaningful marketing and sales alignment.He shares how AI technologies can be leveraged to continuously update and deliver relevant, real-time context about customers, helping teams create more personalized and impactful experiences. Greg also reflects on his own career journey, offering advice on mentorship, self-awareness, and finding purpose in your work.In this episode, we cover:How to move beyond static personas and gain real-time, contextual customer understandingThe role of AI in scaling personalized marketing and keeping insights fresh and actionableWhy product-market fit is a moving target and how to stay aligned with evolving customer needsHow to use customer context as a strategic advantage in sales conversations and GTM planningIf you're a marketing leader looking to elevate your B2B strategy with sharper customer focus and smarter use of AI, Greg’s insights deliver both inspiration and practical guidance.🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.Connect with Greg:LinkedIn: https://www.linkedin.com/in/gregperotto/  Poggio: https://www.poggio.io/ Ways to Tune In:Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/