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  • Why Your Brand Sounds Like Everyone Else's AI-Generated Content: Brett Van Buskirk - Episode # 65
    2026/09/24

    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/

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    48 分
  • Product Marketing in the Age of AI: Beth Barach - Episode #64
    2026/09/18

    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: engineering teams are measured on feature-release velocity, and faster cycles and AI-assisted development only pour more fuel on the fire. Her antidote is to "knit the sweater" by deciding what to market, to whom, and translating technical value into business value.


    Beth shares her playbook for ruthless prioritization, making the case that not every feature should be marketed to everyone. She walks through structured customer listening techniques, including in-room prioritization exercises with red, yellow, and green sticky notes that force real tradeoffs and surface true customer needs. The conversation also covers the growing backlash against "AI slop" in content, how Beth uses AI as an assist for competitive intelligence and organizing notes rather than replacing human judgment, and her non-linear career path from English literature into technology marketing.


    In this episode, we cover:

    • Why "inside-out" messaging persists and how engineering incentives drive feature bloat in the AI era
    • How to "knit the sweater" by choosing what to market, to whom, and translating technical value into business value
    • Structured customer listening techniques, including sticky-note prioritization exercises that force tradeoffs and reveal true needs
    • Using AI as an assist for competitive intelligence and note organization while avoiding "AI slop" in your content

    If you're a marketing leader watching feature-packed messaging fall flat with buyers, Beth's framework for prioritized, customer-first product marketing is one worth stealing.

    🔔 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/bethbarach/
    • Brinqa: https://www.brinqa.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/


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    48 分
  • What Most B2B Marketers Miss When They Chase Digital Scale: Amy Sitnick - Episode #63
    2026/09/03

    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/

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    42 分
  • How to Build an AI-Powered ABM Strategy: Elyssa Steiner - Episode #62
    2026/08/27
    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 understandingHow to build ICP frameworks for multiple verticals in your first 60 days and turn that work into a springboard for AI tools and content strategyHow to scale an ABM strategy from a handful of target accounts to hundreds once AI takes the busy work off your team's plateWhy "don't let comfort make your decisions" is the throughline for marketing leaders moving from individual contributor to CMOIf 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/01kCcPP1ib9MSE9aNb5SQaApple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3diHeart Radio: https://iheart.com/podcast/282837141/Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJVMore 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/
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    47 分
  • Scaling Client Relationships Through Community: Paul Jones - Episode #61 (Re-Air)
    2026/08/20

    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 understanding your Ideal Client Persona (ICP), using empathy to craft resonant messaging, and creating space for meaningful, value-driven interactions. Paul also challenges the overreliance on technology, encouraging marketers to start simple and stay focused on human connection.

    In this episode, we cover:

    • The difference between going to market and connecting to it
    • How to understand your ICP beyond the surface level
    • Why low-tech, high-value engagement builds stronger communities
    • Real examples of community-led product and messaging success

    If you're looking to engage your audience more meaningfully and build communities that drive real connection, this episode offers practical and inspiring insights.

    🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

    Connect with Paul:

    • LinkedIn: https://www.linkedin.com/in/pauljones101/
    • Bridgio: https://bridgio.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/

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    41 分
  • Turning Live Events into Podcast Magic: Casey Cheshire - Episode #60
    2026/08/13

    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 connection, generate buzz around an event, turn conversations into content, and build stronger relationships with prospects and customers.

    Casey shares some of the conversations he’s had with members of the Connect To Market community at Black Hat, including discussions around AI, growth, happiness, and the importance of maintaining a human balance in an increasingly noisy digital world. He also walks through several practical ways to bring a podcast to your next event, from capturing quick “hot takes” to using podcast conversations as a reason for prospects to show up for meetings.

    The episode also explores how live podcasting can create more authentic customer stories, strengthen relationships, and surface the thought leadership already sitting inside your organization. Casey’s takeaway? As AI-generated content and digital noise continue to increase, genuine human connection becomes even more valuable.

    In this episode, we cover:

    • Why live events and podcasts can create a powerful combination for human connection
    • How to use quick “hot takes” to generate buzz and turn event conversations into podcast content
    • Why podcast interviews can give prospects a better reason to show up for meetings
    • How AI and content “slop” are making human connection more important than ever

    If you're heading to a conference or planning your next live event, Casey's playbook offers simple ways to turn the conversations happening around you into meaningful relationships, content, and opportunities.

    🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.

    Connect with Casey:

    • LinkedIn: linkedin.com/in/caseycheshire
    • Website: 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/

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    9 分
  • The AI Prompting Masterclass Every Marketer Needs To Hear: Keven Ellison - Episode #59 (RE-AIR)
    2026/08/06

    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 competitive
    • How to master AI prompts and build scalable workflows
    • How AI is changing the future of work, including CRM and HR systems
    • Why human creativity and business experience remain essential

    If 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-architect

    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/

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    49 分
  • The Pipeline Wake-Up Call Every B2B Marketer Needs to Hear: Randy Brasche - Episode #58
    2026/07/30

    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 metrics. Brasche argues that marketers must understand pipeline coverage multiples, participate in pipeline calls with confidence, and build strategy around ICP definition, account engagement, and the full customer lifecycle, not just top-of-funnel lead generation. He makes the case that the marketers who earn a seat at the revenue table are the ones who can speak the language of pipeline math and tie their work directly to acceleration, churn reduction, and expansion.

    Brasche walks through why most marketers default to volume and conversion metrics that don't resonate with revenue leaders, and how shifting focus to pipeline multiples and lifecycle engagement changes the entire conversation. He breaks down the math behind pipeline coverage, explains how to identify the 10 percent of your market that is actually in-market at any given time, and shares how intent data and ICP refinement can sharpen targeting. The conversation also dives into the AI balance: Brasche outlines how AI can improve ICP definition, context delivery, and messaging quality at scale, but warns that data cleanliness and human oversight are non-negotiable for accuracy.


    In this episode, we cover:

    • Why marketers must learn pipeline coverage math and participate in pipeline calls to earn credibility with revenue leaders
    • How to move beyond volume and conversion metrics to focus on lifecycle engagement, churn reduction, and expansion
    • Using AI to sharpen ICP definition and deliver context at scale while maintaining data cleanliness and human oversight
    • Why personal agency, confidence, and conviction are the most important traits for marketers in the AI era

    If you're a marketing leader who feels disconnected from revenue conversations or unsure how to prove your impact beyond MQLs and conversion rates, Brasche's pipeline-math framework and revenue-proximity mindset is the playbook you need to change the conversation.

    🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market.


    Connect with Randy:

    • LinkedIn: https://www.linkedin.com/in/rbrasche/
    • Spot-On: https://spot-on.com/
    • Adaptive B2B: https://adaptiveb2b.com/
    • Some Assembly Required Book: https://www.amazon.com/dp/B0FJZDXZCK

    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/

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    48 分