Erica Weser

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 so caught up in buyer personas, marketing technology, and analytics that they lose sight of the people they're trying to reach. His advice? Listen, empathize, and understand the problems your customers are actually trying to solve. David shares how a creative approach to marketing helped generate approximately $10 million in leads during his time at IBM, thanks to an unforgettable racetrack experience that brought prospects together through shared excitement and connection. He and Casey discuss how to break through the noise with more engaging marketing, why marketers benefit from spending time in sales, and how to build trust by listening to customers, prospects, colleagues, and even people who've stopped buying from you. David also explains how AI can help marketers synthesize data, research ideal customer profiles, and prioritize next steps, while emphasizing the importance of human judgment and verifying AI-generated insights. Drawing on nearly 20 years at IBM and his current work at Openstream.ai, David shares why marketers need to balance data with intuition and never let technology replace critical thinking. Takeaways: Remember the human behind the buyer persona. Your customers aren't just ICPs, data points, or personas. They're people trying to solve real problems. Empathy and a genuine understanding of their challenges should shape how you market to them. Listen before you launch. When starting a new role or building a strategy from scratch, learn from your colleagues, customers, prospects, and former customers before making changes. Their perspectives can reveal gaps between how your company sees itself and how the market actually perceives you. Make marketing memorable through human connection. David shares how an IBM racetrack event helped build relationships with prospects and generate approximately $10 million in leads. Creating experiences that are genuinely engaging and memorable can build stronger relationships than another standard webinar or sales follow-up. Use AI as a tool, not a substitute for judgment. AI can help synthesize information across CRM data, social listening, analyst sentiment, and PR coverage, as well as support ICP research and prioritization. But marketers still need to verify the results, combine data with intuition and experience, question assumptions, and protect sensitive business information. Links: LinkedIn: linkedin.com/in/thedavidastark  Personal Website: https://davidastark.com/  Company Website: openstream.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/ 

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 and get ruthlessly clear on why you're listening, who you're listening to, and what you're listening for. Suresh breaks down how vendor tools and shiny new tech can quietly end up shaping your strategy, and why writing down the question you want answered is the simplest way to stay on track. He and Casey dig into "ruthless prioritization," including how to say no constructively to peers and executives, and why it's a muscle anyone can build at any level. Drawing on his path from software engineer to Adobe GM to startup CEO, Suresh explains why an operator and owner mindset makes marketers better partners to finance, product, sales, customer success, and HR. He also shares his "knee pain" approach to diagnosing marketing problems, where a pipeline issue often turns out to be a positioning problem. The conversation closes with advice for his younger self: be curious, move fast, talk to more people, and never forget the why. Takeaways: Start with why, who, and what before you pick a tool. Be explicit about the reason you're listening to the market, the people you want to hear from, and what you hope to learn. A clear question, like "where will I find my next 20 buyers?", is a far better starting point than "I need to connect to the market." Practice ruthless prioritization. Time is more precious than money because you don't get it back. Saying no is a skill that gets easier with practice, and it lands best when you explain your reasoning in the context of business priorities and invite the other person into the conversation. Think like an owner, not just a marketer. Understanding finance, product, and the rest of the business helps you build stronger bridges across the company. Don't wait for finance to tell you you're overspending. Ask yourself whether you'd spend this money as an investor, and whether the ROI is there. Diagnose the real problem before you fix the symptom. A weak pipeline may not be a demand gen problem at all. Like knee pain that starts in the ankle, the root cause is often positioning, especially if your product has evolved and you're no longer speaking to the right people. Stay curious, move fast, and keep the why in view. Distractions multiply as technology advances. When you stay anchored to your why, tools become a force multiplier instead of a distraction. Links: LinkedIn: https://www.linkedin.com/in/sbexec/  Website: https://www.qualio.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 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 generation, they need to understand their purpose and get everyone moving toward the same destination. When teams are aligned around a shared "peak" and "path," they can communicate the same core idea in their own voices without sounding scripted or inconsistent. Justin explains how his "peak and path" framework helps organizations clarify where they're going, why they're going there, and how that clarity can shape everything from marketing and sales to recruiting and customer conversations. He also shares why leaders need to listen more closely to the ideas already inside their organizations, using small experiments to build trust instead of dismissing ideas before they're tested. Along the way, he breaks down why demographics aren't always the best way to understand an audience, how brands can identify the trust channels their customers already rely on, and why trying to build a following from scratch is often the wrong approach. The conversation closes with a look at authenticity, audience-specific messaging, and how a brand can turn a clear understanding of its audience into a consistent experience at every touchpoint. Takeaways: Align your team before you market to your audience. Get leadership, sales, marketing, HR, and other teams aligned around a shared purpose and direction. Justin's "peak and path" framework gives organizations a clear North Star while leaving room to adapt how they get there. Listen to the ideas already inside your organization. Great ideas don't always need more creativity. They need leaders who are willing to listen, empathize, and build trust. Small experiments can help teams test ideas and prove their value before making a bigger investment. Find where your audience already trusts you. Don't try to build a following from scratch. Talk to your existing customers and identify the publications, events, communities, people, and other channels they already rely on for information. Understanding your audience's shared values can be more useful than relying on demographics alone. Keep your message consistent, but make it relevant. Authenticity doesn't mean saying the exact same thing to everyone. Your company's core purpose should stay consistent, while the way you communicate it can shift based on who you're talking to and what matters to them. Links: LinkedIn: https://www.linkedin.com/in/justinbrady/ Website: https://justinkbrady.com/  Trust Channels: https://justinkbrady.com/trust-channels/  Twitter: https://x.com/JustinBrady  Podcast: https://justinkbrady.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 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 open-minded, listening closely, and adapting to what happens in the moment can lead to better customer conversations and stronger strategies. Danielle explains how marketers can apply the principles of improv by setting aside assumptions, embracing the information customers provide, and using a “yes, and” mindset rather than telling customers what they need. She also shares her approach to “market-led marketing,” from attending industry events and listening to the questions people are asking to building small experiments and following the solutions that gain traction. Plus, Danielle discusses the importance of human connection in building customer advocates, why your network can shape your career, and her cardinal rule for using AI: you can’t use AI to do something you can’t do yourself. Takeaways: Approach your market with an open mind. Set aside your assumptions and let customers establish the “scene.” Ask questions, listen to what they are experiencing, and adapt your strategy based on what you learn. Use “yes, and” to create better customer conversations. Rather than telling customers what they need, embrace what they tell you and build from there. Marketing should be a reciprocal conversation, not a constant stream of features and messaging. Let the market lead your marketing. Danielle recommends going to industry events, listening to the conversations and questions happening around you, and using those insights to identify problems worth solving. Start small, test an MVP, and follow where your audience leads you. Use AI to amplify your skills, not replace them. AI can help you learn, improve your work, and move faster, but marketers still need to understand the fundamentals behind what they are creating. Without that foundation, it becomes much harder to recognize or fix what AI gets wrong. Links: LinkedIn: https://www.linkedin.com/in/danielleradden/ Website: https://magicdoor.com/  Danielle’s Book: https://a.co/d/027qeSUQ  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/ 

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 distribution problem, so scale and speed are no longer differentiators. What's left is authenticity: leaders and brands willing to be curious, show up in person, and represent themselves as people rather than repeating company lines. Brett walks through why "sounding like a robot" is now a liability, drawing on his time visiting small businesses at Intuit and building one of the first digital mortgage apps at Blend, where his team assumed loan officers wanted to manage deals from their phones while out of the office, only to learn they'd rather just call their team back at the desk. It's a sharp reminder that even well-researched personas can miss how people actually want to work. He also makes the case for taking bigger creative risks since most of them carry less downside than marketers assume, and shares how he's applying AI internally for competitive intelligence while still insisting that curiosity and direct customer observation can't be automated. The conversation closes with Brett's non-linear path from consulting to product marketing, and his advice for giving yourself permission to grow at your own pace instead of chasing every trend on LinkedIn. In this episode, we cover: Why AI has removed the old distribution barrier and made "sounding like everyone else" marketing's biggest new risk How real customer observation, like watching a shopkeeper manage inventory or seeing loan officers actually work in the field, surfaces insights research alone won't A three-move, no-budget framework for connecting to market: authentic social presence, mining your own customer intelligence, and getting close to product decisions Why marketers systematically overestimate risk, and how to build a career and a brand around calculated, uncomfortable bets Links: LinkedIn: https://www.linkedin.com/in/brettvanbuskirk/  Website: https://trueml.co/  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/ 

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 your industry is the real starting point for any go-to-market strategy, and that the fastest way to learn what they need is to sit down with the people who talk to them every day, from client-facing colleagues to the sales reps carrying the target list. She walks through how one conversation with her sales team about a stalled emerging product turned into a direct mail campaign built around a tech-enabled water bottle and a personal note, a play that got some of their most hard-to-reach prospects to respond after everything digital had failed. Amy also gets into her three-move framework for building a connect-to-market strategy with zero ad budget: interview internal subject matter experts like customer success reps, not just the C-suite, for thought leadership content; partner with the smaller, industry-specific influencers who can actually speak to your buyers; and treat sales enablement as free marketing that just needs the right content behind it. She's candid about where AI is helping her team, including a branded PowerPoint template that keeps AI-generated content on-brand, and where it's making marketing noisier, cautioning that without a human in the loop your brand can turn into "a walking em dash." Amy also opens up about her path from studying Spanish and international relations to running B2B marketing across financial services and now life sciences, and the shift in mission that came with it, from helping people reach their financial goals to giving patients hope. In this episode, we cover: Where to look inside your own company for the subject matter experts and stories that make thought leadership actually credible Why unique, unexpected outreach can outperform digital channels when it's backed by real research into a prospect's pain points How to pick influencer partners based on relevance to your buyers rather than follower count What it takes to scale content production with AI without losing the authenticity that makes a brand trustworthy How tying your team's work to a greater sense of purpose changes the way marketing shows up day to day Links: LinkedIn: https://www.linkedin.com/in/amysitnick/  Website: https://www.viedoc.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 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 it can't invent what you haven't learned yet, and that field visits, sales call shadowing, and trade show attendance are what turn AI-synthesized data into real buyer insight. She shares how she used her first 60 days as CMO to build ideal customer profile (ICP) frameworks for nine core verticals, why she sends a marketer to every trade show her company exhibits at, and how listening in on sales calls became one of the highest-value habits on her team. Elyssa walks through how Kahua's AI adoption evolved from basic custom GPTs to purpose-built AI skills and an account-based marketing (ABM) agent that scaled the team's target account list from a capacity-constrained "Magic 18" to more than 400 one-to-one and one-to-few accounts. She breaks down why she believes the most critical skill for a modern marketer is being a really good editor, not a really fast prompter, and how her team is shifting from repetitive execution work into real marketing strategy as AI takes over the busy work. She also opens up about her own career path from retail buying to startup sales to CMO, and the philosophy that has shaped her decision-making ever since: hard choices, easy life; easy choices, hard life. In this episode, we cover: Why closing the physical distance between marketing and the buyer, not just better AI tools, is what actually builds buyer understanding How to build ICP frameworks for multiple verticals in your first 60 days and turn that work into a springboard for AI tools and content strategy How to scale an ABM strategy from a handful of target accounts to hundreds once AI takes the busy work off your team's plate Why "don't let comfort make your decisions" is the throughline for marketing leaders moving from individual contributor to CMO If you're a marketing leader trying to figure out how AI actually fits into your team's workflow without losing the human judgment that makes marketing work, Elyssa's approach to pairing field experience with AI-powered execution is the playbook you've been missing. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Elyssa: LinkedIn: https://www.linkedin.com/in/elyssasteiner/ 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 More About Elyssa:  Elyssa Steiner is Chief Marketing Officer at Kahua and a B2B growth leader with more than 15 years of experience building brands, leading high-performing teams, and developing integrated marketing strategies that drive pipeline, customer engagement, and measurable business growth. At Kahua, she leads the company’s marketing vision and go-to-market strategy across brand, demand generation, product marketing, customer advocacy, and marketing operations. She is also advancing an AI-fluent approach to marketing, using AI to uncover insights, scale execution, and improve efficiency while keeping strategy, creativity, and customer understanding at the center. Before joining Kahua, Elyssa served as Chief Marketing Officer at Cantaloupe, where she helped guide the company through a period of significant growth and transformation. During her final two years, Cantaloupe grew annual recurring revenue from approximately $250 million to $310 million while she led marketing through multiple acquisitions, portfolio and brand integration, and the company’s eventual sale. Her expertise spans revenue-driven marketing, go-to-market strategy, sales alignment, customer growth, fintech, and emerging technology. She has shared her perspective on The Revenue-Driven CMO, multiple Leaders in Payments episodes, and a live Marketing on Mars CMO panel in San Francisco. Elyssa holds a master’s degree in Communication and Leadership from Gonzaga University and a bachelor’s degree in Business and Marketing from the University of Washington. Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/