In this episode of Connect To Market, host Casey Cheshire welcomes Melissa Moody, Founder of Wednesday Women and Host of the Joy of Connecting podcast, to explore how brands can drive growth by returning to authentic human relationships. Melissa introduces her “concentric circles of influence” framework, a practical approach to prioritizing the people closest to your business first, employees, leaders, and internal advocates, before expanding outward to investors, partners, customers, and ultimately the broader market. She explains why starting from the inside out creates stronger alignment, clearer storytelling, and more effective market engagement.

She breaks down how organizations can activate employees as brand storytellers, align incentives with investors and advisors to unlock opportunities, and build strategic partnerships as a scalable growth lever. Melissa also highlights the importance of customer success as a marketing function, emphasizing customer-driven content over feature-heavy messaging. From prioritizing inner circles in small teams to maintaining brand consistency at scale, she outlines a more human, relationship-first approach to modern go-to-market strategy.

In this episode, we cover:

• Why human connection outperforms automation in today’s noisy marketing landscape

• Understanding and applying the concentric circles of influence framework

• Enabling employees and internal stakeholders as authentic brand advocates

• Leveraging partnerships and customer success as powerful growth drivers

If you’re a marketing leader looking to build stronger relationships, create more authentic engagement, and scale your impact from the inside out, Melissa’s framework offers a clear and actionable path to connecting with your market in a more meaningful way.

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

Connect with Melissa:

• LinkedIn: https://www.linkedin.com/in/melissammoody/

• Wednesday Women: wednesdaywomen.org

• Joy of Connecting Podcast: https://www.joyofconnect.ing/

• Alaska Salt Company: https://alaskasaltco.com/

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/

In this episode of Connect To Market, host Casey Cheshire welcomes Ian Dowe, Senior Vice President Marketing at HealthAxis, to explore how marketers can connect to their market through a deeply data-driven foundation. Ian explains why understanding your total addressable market, identifying active buyers, defining ICPs and personas, and mapping solutions to real pain points must come before any campaign execution. He shares how gaps in this foundation often stem from organizational maturity and why early success can create false confidence as markets inevitably shift.

He breaks down how leaders can build from the ground up by aligning product to buyer needs using frameworks like the KANO model, then layering in narrative, brand, and go-to-market strategy. From structuring MarTech stacks and internal processes to defining product marketing roadmaps and revenue metrics, Ian outlines a practical, step-by-step approach to building a scalable marketing engine. He also reframes creativity as strategic problem-solving and challenges teams to rethink websites as buyer enablement platforms that educate and qualify prospects deeper in the funnel.

In this episode, we cover:

• Why a strong data-driven foundation is critical before executing marketing campaigns

• Aligning product, messaging, and GTM strategy using buyer needs and the KANO model

• Reframing websites as buyer enablement platforms that drive deeper funnel engagement

• Building scalable marketing systems across MarTech, processes, and revenue metrics

If you’re a marketing leader looking to strengthen your GTM foundation while turning your website into a true growth engine, Ian’s approach offers a clear roadmap for building, scaling, and adapting in an ever-changing B2B landscape.

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

Connect with Ian Dowe:

• LinkedIn: https://www.linkedin.com/in/ian-dowe/

• Health Axis Group: healthaxis.com

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/

💡 5 Key Trade Show ROI Takeaways for Marketing Leaders

1️⃣ Booth experience drives engagement more than booth size
Across discussions, one theme was clear: bigger booths don’t guarantee better outcomes. Attendees called out cluttered visuals, unclear messaging, and uninviting layouts as major blockers. High-performing booths were described as visually simple, easy to navigate, and designed for conversation, not just visibility. If attendees don’t immediately understand what you do within 3–5 seconds, conversion drops.

2️⃣ Most booths fail the “clarity test”
Multiple participants noted that unclear or overly dense messaging is one of the biggest missed opportunities. Walls filled with text, vague positioning, or competing messages create friction. The takeaway: your booth should answer three questions instantly- who you help, what you do, and why it matters. Anything beyond that should support, not compete.

3️⃣ Lead quality > lead volume (and requires intentional filtering)
Teams shared that without a clear qualification strategy, booths attract high volumes of low-intent leads. One example: using codewords or structured demo gating to distinguish real prospects from giveaway seekers. The highest-performing teams intentionally design friction into the process to improve lead quality because unqualified leads inflate ROI metrics without driving pipeline.

4️⃣ Giveaway strategy should match event scale and intent
There was strong alignment that giveaways are context-dependent. At large, high-traffic events, they can increase booth traffic but often dilute lead quality. At smaller or more targeted events, they’re often unnecessary. The insight: giveaways should support a conversion strategy, not replace one. If they aren’t tied to engagement or qualification, they become a cost center.

5️⃣ ROI starts before the event with targeting and intent
One of the most practical takeaways: who you bring to the booth matters more than who walks by it. Leaders emphasized being more intentional about pre-event outreach, identifying ideal attendees, and actively pulling the right people into conversations. Trade show success isn’t just about presence, it’s about precision in who you engage.

The through line: trade show ROI isn’t created on the floor, it’s designed ahead of time and executed with discipline. When messaging is clear, engagement is intentional, and qualification is built in, events shift from a cost center to a pipeline driver.

Community Leader Casey Cheshire was joined by Paul Jones, Pardees Safizadeh, and Aaron Rayner to unpack how in-person events are regaining momentum as buyers seek real human connection in an increasingly AI-saturated landscape. The group explored how to design booths that attract the right audience instead of maximizing volume, how live conversations accelerate trust and pipeline movement, and why event strategy should prioritize quality of interaction over quantity of leads.

This was not just a recap, it was a practical, strategy-first conversation about how to turn trade shows into a high-impact growth channel by aligning experience, targeting, and follow-through to revenue outcomes.

Key takeaways:

• In-person events are resurging as buyers crave authentic, human connection, making trade shows a powerful channel for building trust and accelerating pipeline

• Booth strategy should focus on attracting the right “fish,” prioritizing ideal customers and meaningful conversations over high volumes of badge scans

• Real-time, face-to-face interactions create faster relationship-building opportunities that can move deals through the pipeline more efficiently than digital-only touchpoints

• Every interaction matters, as even non-buyers can influence decisions through the dark funnel, reinforcing the need for thoughtful engagement across all booth conversations

Whether you are rethinking your event strategy, optimizing booth performance, or looking to better connect trade show activity to pipeline impact, this session delivered actionable insight to help marketing leaders turn in-person moments into measurable growth.

Connect To Market is where real conversations turn into real strategies. Be a part of an exclusive community of B2B marketing leaders driving growth. We meet monthly on Zoom to tackle current challenges and engage in meaningful breakout discussions. Ready to connect? Get on the list for the next event!

Submit a Request Here!

Subscribe to our Substack for first access to every podcast episode, powerhouse panel, and exclusive content that’s redefining the future of marketing and connecting with your buyers.

Subscribe now

Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

Our latest CTM lightning talk featured Bill Kenney challenging a common assumption: a busy booth doesn’t mean a successful one. Bill introduces a booth assessment framework focused on a booth’s ability to attract the right prospects and help them self-identify, sharing that in a review of 500 exhibitors, only a handful met the mark. Using a “fish, waters, bait” metaphor, he explains how marketers must clearly define who they’re targeting, where those prospects are, and what messaging or offers will actually draw them in. He emphasizes that in B2B and B2G environments, the goal isn’t to close deals on the floor… It’s to create qualified meetings. From avoiding “prospect creep” to crafting five-words-or-less headlines and aligning giveaways with intent, Bill shows how clarity and discipline drive better outcomes. If your booth is attracting attention but not pipeline, this session is a must-watch.

In this lightning talk, we cover:

• Defining true prospects based on need, budget, and urgency

• Using the fish, waters, bait framework to guide booth strategy and messaging

• Creating simple, compelling headlines that attract and qualify the right audience

• Designing giveaways and experiences that reinforce positioning instead of diluting it

Huge thank you to Bill Kenney for sharing a practical framework that helps teams move beyond vanity metrics and build trade show strategies that drive real pipeline.

Connect To Market is where real conversations turn into real strategies. Be a part of an exclusive community of B2B marketing leaders driving growth. We meet monthly on Zoom to tackle current challenges and engage in meaningful breakout discussions. Ready to connect? Get on the list for the next event!

Submit a Request Here!

Subscribe to our Substack for first access to every podcast episode, powerhouse panel, and exclusive content that’s redefining the future of marketing and connecting with your buyers.

Subscribe now

Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

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

Bill breaks down why traditional booth setups often fall short and how a customer-centric approach makes all the difference. He shares how focusing on pain-point-driven messaging, like asking direct, relatable questions, can immediately attract qualified prospects. Bill also emphasizes the importance of keeping booth designs clean and simple, ditching cluttered text and irrelevant graphics for bold headlines that speak to real customer needs. Plus, he explains how to train your team for short, high-impact conversations and collect the right data for post-show follow-up.

In this episode, we cover:

• Why customer-focused booth messaging outperforms company-centric designs

• The power of short, strategic conversations over lengthy sales pitches

• Why cluttered booths and generic giveaways can hurt your brand presence

• Bill’s framework for turning trade shows into high-performing lead gen channels

If you’re ready to transform your trade show booth into a lead-generating powerhouse, this episode is packed with actionable insights you won’t want to miss!

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

Connect with Bill:

• LinkedIn: https://www.linkedin.com/in/bkenney/

• MEET Company: https://meetroi.com/

• Blog: https://meetroi.com/blogs/

• Belly 2 Belly Podcast: http://meetroi.com/podcast/

• Softland Partners: https://softlandpartners.com/

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/

In this episode of Connect To Market, host Casey Cheshire welcomes B2B GTM Leader Angela Earl to explore how organizations can strengthen their connection to customers by listening more closely- not just to feedback, but to the real conversations happening across their teams. Angela explains why the most valuable insights often emerge when things aren’t going well, and why leaders must create an environment where honesty and vulnerability are encouraged so teams feel comfortable sharing what they’re truly hearing from customers.

She shares why building a shared understanding of the customer across go-to-market teams is critical, and how marketers can capture real signals such as objections, friction points, and recurring questions through tools like call transcripts and systems like Salesforce or HubSpot. Angela also emphasizes the importance of establishing a regular cadence to review feedback and ensure insights move across teams rather than getting lost in isolated systems. From using AI to accelerate research to validating insights through real conversations, she outlines practical ways leaders can stay close to the voice of the customer.

In this episode, we cover:

• Why real conversations often reveal more than polished customer feedback

• Building a shared understanding of the customer across go-to-market teams

• Capturing and sharing real customer signals through tools and systems

• Creating a regular feedback cadence to prevent insights from getting stuck in silos

If you’re a marketing leader looking to strengthen alignment across teams while staying closer to the voice of the customer, Angela’s approach offers practical ways to turn everyday conversations into meaningful market insight.

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

Connect with Angela:

• LinkedIn: https://www.linkedin.com/in/angelanearl/

• Book: https://a.co/d/1oth0TT

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/

In this episode of Connect To Market, host Casey Cheshire welcomes Valerie Zargarpur, Head of Marketing at Monad, to explore how marketers can connect to their market through brand story rather than just visual identity. Valerie explains why B2B, especially cybersecurity, often relies on jargon and executive-focused messaging, even though day-to-day users champion products. She shares why focusing on real customer insights and validated use cases can help brands stand out and build trust in a crowded market.

She breaks down how leaders can move from generic messaging to earning understanding by listening to customers, reviewing sales conversations for themes, challenging assumptions about the ideal customer profile, and positioning around use cases that resonate. From creating cohesive go-to-market narratives to leveraging origin stories for brand personality, Valerie outlines practical ways to differentiate and connect with audiences. She also reflects on iterative testing of messaging and applying B2C lessons in niche B2B contexts.

In this episode, we cover:

• Why B2B and cybersecurity brands often blend in and how storytelling can differentiate them

• Building a cohesive narrative from customer insights and validated use cases

• Leveraging origin stories to create brand personality and emotional connection

• Iterative testing of messaging to ensure clarity, simplicity, and resonance

If you’re a marketing leader looking to break through the noise while building deeper market trust, Valerie’s approach offers a clear roadmap for sharpening positioning, increasing credibility, and connecting with real users through authentic brand story.

🔔 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-zargarpur/

• Monad: https://www.monad.com/

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/.

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 influence

• How to define the right problem through customer conversations

• How category maturity shapes whether you evangelize, niche down, or lead

• Why strategy must be distilled into a narrative that aligns teams and drives growth

If 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:

• Apple Podcasts:

• 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/

Community Leader Casey Cheshire was joined by Chris Silvestri, Sarah Lubeck, Brandon Pittser, Beth Magee, Alex Schutte, Greg Matranga, Julie Edgett, and Emma Vas to unpack how SaaS marketing performance is increasingly measured by pipeline contribution, attribution clarity, and revenue impact. The group explored how to operationalize messaging into scalable sales playbooks, how evolving sales motions reshape attribution strategy, and why continuous research, especially recent-buyer interviews and win-loss analysis, is essential as procurement models and funding environments shift.

This was not just a recap, it was a practical, systems-level conversation about how to ensure messaging is not just well-written, but revenue-aligned, research-backed, and built to adapt in changing markets.

Key takeaways:

• Marketing must tie messaging directly to measurable pipeline impact by aligning conversion points, attribution models, and reporting systems end-to-end

• Scalable sales enablement starts with a universal messaging framework and extends into persona-specific ICP playbooks with tailored value propositions, pitches, proof points, and channel-ready assets

• Jobs-to-be-done research uncovers decision psychology before, during, and after purchase, enabling more emotionally resonant, one-person-focused messaging grounded in real buyer context

• Consistent research cadence, including quarterly surveys, monthly win-loss calls, and interviews with recent customers, helps teams adapt positioning as procurement shifts and ROI expectations intensify

Whether you are refining your ICP, evolving attribution models, or rebuilding positioning for a changing buyer landscape, this session delivered actionable insight to help marketing leaders connect message to market and market to pipeline.

Connect To Market is where real conversations turn into real strategies. Be a part of an exclusive community of B2B marketing leaders driving growth. We meet monthly on Zoom to tackle current challenges and engage in meaningful breakout discussions. Ready to connect? Get on the list for the next event!

Submit a Request Here!

Subscribe to our Substack for first access to every podcast episode, powerhouse panel, and exclusive content that’s redefining the future of marketing and connecting with your buyers.

Subscribe now

Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

Our latest CTM lightning talk featured Chris Silvestri unpacking a hard truth: when pages and ads aren’t converting, the problem usually isn’t the copy. Chris breaks down “message-market fit” as delivering the right message to the right audience at the right time, in the right language and explains why most teams jump straight to rewrites, redesigns, or random A/B tests instead of addressing the deeper issue. He walks through the three-layer research model that separates surface-level voice-of-customer insights from structural behavioral data and deep buyer psychology. From internal alignment workshops and competitive positioning exercises to applying Jobs-to-be-Done and the Four Forces of Progress, Chris shows how positioning drives messaging, messaging drives copy, and alignment drives revenue. If your team keeps tweaking headlines without fixing strategy, this session is a must-watch.

In this lightning talk, we cover:

• Understanding message-market fit and why copy is the final layer, not the starting point

• The three research layers and how to uncover real differentiation through internal, user, and market insights

• How to translate positioning into messaging pillars, value stacks, and strategic narrative

• Writing conversion-focused copy that mirrors buyer psychology, builds trust with proof, and addresses switching friction

Huge thank you to Chris Silvestri for delivering a practical, research-driven framework that helps teams stop chasing surface fixes and start building messaging systems that truly convert.

Connect To Market is where real conversations turn into real strategies. Be a part of an exclusive community of B2B marketing leaders driving growth. We meet monthly on Zoom to tackle current challenges and engage in meaningful breakout discussions. Ready to connect? Get on the list for the next event!

Submit a Request Here!

Subscribe to our Substack for first access to every podcast episode, powerhouse panel, and exclusive content that’s redefining the future of marketing and connecting with your buyers.

Subscribe now

Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

💡 5 Key Messaging & Positioning Takeaways for Marketing Leaders

1️⃣ Messaging breakdowns are usually executive alignment problems
Several VPs shared that friction stemmed from founder disagreement or CEOs holding onto legacy positioning (in one case unchanged for 8 years). When leadership isn’t aligned on what the company does, the market won’t be either. For VPs, messaging work often means facilitating executive alignment first. Internal clarity precedes external traction.

2️⃣ Product-centric messaging is the default… and the trap
Many teams defaulted to feature-heavy narratives or tried to highlight “all the use cases.” One company spent 3 years refining positioning before narrowing to 2–3 core use cases, which finally created clarity. Focus increases authority. Broad capability lists dilute it.

3️⃣ Messaging evolution is an influence challenge, not just a copy exercise
Across industries, leaders noted that updating positioning required more than better frameworks. It meant aligning executives, navigating strong opinions, and reframing debates around business impact. Bringing customer interviews, win/loss data, and pipeline insights into the room shifts the conversation from preference to performance.

4️⃣ Market shifts demand structural rewrites
Acquisitions, category creation, new procurement models, and AI-driven markets are forcing teams to rebuild messaging pillars. When ICP, GTM motion, or buyer behavior changes, incremental edits are not enough. Positioning must evolve with strategy.

5️⃣ The strongest teams treat messaging as a revenue lever
Leaders confident in their positioning tied messaging directly to pipeline and sales impact. They prioritized customer insight, differentiation, and iteration. Messaging isn’t about sounding good. It’s about making revenue easier and reducing friction across the funnel.

The through line: messaging clarity requires prioritization and executive courage. When the narrative sharpens, everything downstream improves.

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 brands

• How specificity and niche positioning improve AI visibility

• Practical strategies for trust-building through education and comparisons

• The 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:

• Apple Podcasts:

• 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/

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 marketing

• How AI is transforming marketing strategies and consumer expectations

• Practical strategies for fostering customer loyalty and advocacy
  Ethical considerations in AI-driven marketing and algorithmic pricing

If 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/

• ChiefMartec: chiefmartec.com

Ways to Tune In:

• Spotify:

• Apple Podcasts:

• 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/

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 marketing

• How to overcome internal gatekeeping and fear of customer feedback

• Practical methods for uncovering deeper customer pain points

• How AI and emerging technologies are influencing modern marketing strategies

If 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:

• Apple Podcasts:

• 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/

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 company

• How AI can help uncover the questions buyers are truly asking

• The role of long-form, evergreen content alongside short, digestible formats

• Why clarity, frameworks, and authentic helpfulness drive standout marketing

If 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:

• Apple Podcasts:

• 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/

Community Leader Casey Cheshire and Community Moderator Paul Jones were joined by members Al Sargent, Deborah Szajngarten, Erica Lanyon, and Kerry Pearce to reflect on the biggest challenges and opportunities in attribution today, from the impact of new digital channels and AI, to the growing importance of brand presence and trust. The discussion explored how leaders can move beyond last-click thinking, leverage AI for smarter CRM integration, and make sense of attribution in an environment where influence is rarely linear.

This wasn’t just a recap- it was a practical, forward-looking exchange on how attribution is evolving and how marketing leaders can adapt with clarity and confidence.

Key takeaways:

• Attribution is becoming more complex as digital channels and customer journeys continue to expand

• AI plays a growing role in improving attribution models and integrating insights across CRM systems

• Measuring presence and long-term brand impact is just as important as tracking short-term conversions

• In a multi-touch environment, success requires balancing data, strategy, and brand trust

Whether you’re navigating attribution challenges, exploring AI-powered measurement tools, or focusing on building durable brand presence, this session delivered actionable insights to help you lead effectively in the digital age.

Connect To Market is where real conversations turn into real strategies. Be a part of an exclusive community of B2B marketing leaders driving growth. We meet monthly on Zoom to tackle current challenges and engage in meaningful breakout discussions. Ready to connect? Get on the list for the next event!

Submit a Request Here!

Subscribe to our Substack for first access to every podcast episode, powerhouse panel, and exclusive content that’s redefining the future of marketing and connecting with your buyers.

Subscribe now

Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

💡 5 Key Attribution Takeaways from the Community

1️⃣ Confidence in attribution is partial but directionally useful
Most teams reported 50–70% confidence in their attribution models. Digital channels (paid, organic, LinkedIn, newsletters) are easier to track, while direct traffic, events, referrals, and long-tail influence remain persistent blind spots. Despite imperfections, teams are still using attribution directionally to guide budget decisions.

2️⃣ Events and “direct” remain the hardest to measure but the most influential
In-person events, trade shows, booths, and community touch points repeatedly surfaced as high-impact but difficult to attribute. Deals often closed months- or years-later, making first- and last-touch models insufficient. When events were aggregated together, they often emerged as the top pipeline driver post-pandemic.

3️⃣ AI is creating a new attribution gap marketers are racing to close
AI-driven discovery (ChatGPT, Gemini, Perplexity, Copilot) is already influencing pipeline, yet most teams lack reliable attribution beyond self-reported form fields. While tools like HubSpot now surface “AI” as a source and platforms like Peek AI attempt to identify AI search queries, marketers expressed frustration at not being able to confidently say, “This deal came from AI.”

4️⃣ The conversation is shifting from credit to contribution
Several leaders emphasized the need to move attribution discussions away from defensiveness and toward business impact. Rather than debating first vs. last touch, the focus is increasingly on cascading activities- sales, marketing, product, content, events, and community- working together to move deals forward in long, multi-year buying journeys.

5️⃣ Better questions matter more than perfect models
Advanced teams are reframing attribution as a tool for insight, not validation. Instead of asking “Which channel gets credit?”, they’re asking:

• What consistently fills pipeline?

• What accelerates deals?

• Where should we lean in- even if measurement is imperfect?
  This mindset is helping marketing leaders communicate value to executives, guide investment decisions, and stay aligned with sales- even as attribution remains inherently incomplete.

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 messaging

• How internal alignment and competitive analysis drive team success

• The role of AI personas and human-driven copywriting in crafting messaging

• Practical steps to differentiate your offerings and refine your value proposition

If 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:

• Apple Podcasts:

• 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/

“The number one thing marketers need to do to connect to the market is know the market.” - David Schnepp

It sounds obvious. That may be exactly why so many teams skip it.

Knowing the Market Isn’t a Line Item

Schnepp, a B2B SaaS marketing leader and VP of Marketing at Virdee, argues that “knowing your market” isn’t a box you check during onboarding.

It’s a continuous practice.

Marketing teams often prioritize hiring specialists; PPC experts, SEO managers, growth tacticians, without asking a deeper question: Do we actually understand the industry we serve?

That gap doesn’t just affect marketing. It shows up in product decisions, sales conversations, customer success, and leadership choices. When assumptions go unchallenged, teams end up optimizing for a market that no longer exists.

“You have to become a nerd,” Schnepp says.
An absolute nerd about your industry, your buyers, and your users.

Expertise Starts With Curiosity

True market understanding doesn’t come from a single report or survey. It comes from repeated exposure.

Schnepp describes visiting hotels simply to observe how things work. Staying curious about how guests interact with systems. Paying attention to how check-in experiences differ between boutique hotels and large brands.

The point isn’t perfection. It’s proximity.

Markets evolve. Buyer expectations shift. Assumptions that were true four years ago may quietly break while teams stay busy executing yesterday’s strategy.

That’s why Schnepp believes leaders must intentionally carve out time to step back and re-learn the industry again and again.

The Leadership Mandate

This kind of learning can’t be optional or personal-only. It has to be cultural.

Schnepp is clear that market understanding must start at the top. If leadership doesn’t protect time for learning, curiosity gets squeezed out by urgency.

When organizations run at full utilization, learning feels like a luxury. In reality, it’s an investment.

Products improve. Marketing sharpens. Customer conversations become more natural. Teams stop guessing.

“If you don’t understand the market,” Schnepp warns, “you may not fail immediately. But others will pass you.”

Why Short-Term Pressure Breaks Long-Term Strategy

One of the most damaging dynamics Schnepp sees is the expectation that new marketing leaders deliver results immediately.

Thirty-day turnarounds. Sixty-day transformations. Ninety-day miracles.

Without time to understand the nuances of the business and the market, leaders are forced to guess. They rely on what worked somewhere else, in a different industry, with different buyers.

That’s why so many marketing leaders cycle in and out. Not because they lack skill, but because they’re asked to perform without context.

Learning Happens Everywhere

Market learning doesn’t only happen through formal research.

Schnepp studies kiosks at airports, coffee ordering flows, and restaurant policies. He notices when experiences work and when they fail.

Case in point, one of his favorite sports bars recently implemented a new rule where every area of the restaurant has to have the sound on for a football game… or not at all. For 15 years, Schnepp and fellow University of Michigan alumni had met at this bar to watch football games, with a small outdoor area reserved for them, with the sound on. They were the only patrons there early on a Saturday morning, and the bar staff couldn’t explain the justification for the new rule. As a result, the group left the bar and will find a new location from now on. The restaurant lost out on loyal customers due to a cut-and-paste policy.

For Schnepp, those moments are lessons.

“What not to do” can be as powerful as best practices.

Conferences, Contrarian Ideas, and Signals

Schnepp values trade shows not just for sessions, but for observing patterns.

What are vendors selling?
What ideas are gaining traction?
What tactics feel new or newly relevant?

One example that stood out: modern direct mail.

Not flyers. Thoughtful, industry-relevant packages tied to account-based marketing. Physical experiences designed to break through digital fatigue.

Whether or not every idea works, the signal matters. Markets speak through behavior.

Learning Is a Team Sport

A leader’s job isn’t to be the smartest person in the room.

Schnepp believes leaders should synthesize insights, share what they learn, and empower specialists to deepen their expertise.

That requires trust, time, and consistency. Saying “learning matters” without giving people space to do it creates friction instead of growth.

Culture isn’t what you say. It’s what you make possible.

A Career Built on Curiosity

From growing up between Austria and the U.S. to working across industries and continents, Schnepp credits curiosity for shaping his leadership style.

Early in his career, he admits, he lacked emotional intelligence. He was direct, confident, and often wrong about how his ideas landed.

That changed when he learned to listen more, observe more, and question his own assumptions.

Leadership, like market understanding, is learned not inherited.

The Core Lesson

Marketing doesn’t start with campaigns.
It starts with care.

Care enough to watch.
Care enough to ask.
Care enough to admit what you don’t know.

When marketers stop being students of their market, they don’t just lose relevance, they lose direction.

And as Schnepp reminds us, the market is always teaching.
You just have to be paying attention.

Key Takeaways for Marketing Leaders

• Market knowledge is not a phase. It’s a habit.

• Assumptions expire faster than strategies.

• Learning must be modeled and protected by leadership.

• Short-term pressure creates long-term blind spots.

• The world is a classroom… if you’re curious enough to notice.

Final Thought
You don’t connect to the market by speaking louder.
You connect by listening longer.

And the marketers who win won’t be the loudest, they’ll be the most curious.