<![CDATA[The Connect to Market (CTM) Community]]>https://www.connecttomarket.comhttps://substackcdn.com/image/fetch/$s_!0Zku!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd48bd9b1-b54c-4280-9bca-52d4ee8836e4_1280x1280.pngThe Connect to Market (CTM) Communityhttps://www.connecttomarket.comSubstackTue, 19 May 2026 04:34:12 GMT<![CDATA[Making Your CEO a Thought Leader That Gets Heard: Takeaways from our May CTM Event]]>https://www.connecttomarket.com/p/making-your-ceo-a-thought-leaderhttps://www.connecttomarket.com/p/making-your-ceo-a-thought-leaderMon, 18 May 2026 19:37:26 GMTLast week, our community explored a topic that many companies know matters but still struggle to execute well: executive thought leadership. What started as a discussion about helping CEOs build visibility quickly expanded into conversations around consistency, executive buy-in, storytelling, ROI, and the growing importance of authentic human perspectives in an AI saturated market.

From tactical execution challenges to broader conversations about trust and credibility, marketing leaders unpacked what makes executive thought leadership resonate, what causes programs to stall internally, and why the companies seeing traction are treating it as a long-term brand strategy instead of a short-term content initiative.

💡 5 Key Takeaways on Executive Thought Leadership

1️⃣ Thought leadership only works when it is rooted in a real point of view

Across discussions, one theme was clear: thought leadership is not just executives posting content more often. Participants consistently described strong thought leadership as sharing a unique perspective, helping audiences understand industry change, and talking about customer problems without overtly selling. The strongest executive voices are the ones who consistently teach, challenge, or clarify something meaningful.

There was also broad agreement that effective executive thought leadership stays closely tied to the company’s purpose and positioning. Generic commentary and trend chasing rarely stand out. The executives who break through are the ones who can clearly communicate what they believe and why it matters to their audience.

The takeaway: audiences can quickly tell the difference between content created to promote and content created to genuinely provide value. The strongest executive voices consistently offer insight people cannot easily get elsewhere.

2️⃣ Executive buy-in is usually the biggest challenge

A recurring challenge throughout the discussion was that getting executives to consistently participate in thought leadership efforts is difficult for reasons that go beyond scheduling. Some leaders dislike being on camera. Others feel uncomfortable being publicly visible or vulnerable. Several attendees also pointed out that many executives struggle to see a direct connection between thought leadership and measurable business outcomes.

Timing emerged as another major factor. Participants noted that organizations often have the easiest time building executive thought leadership habits early, especially during earlier growth stages before calendars become overloaded and routines become fixed.

The takeaway: successful executive thought leadership programs depend heavily on understanding what motivates individual leaders and making participation feel strategically valuable and manageable.

3️⃣ Consistency matters more than polish

If there was one operational theme repeated throughout the discussion, it was consistency. Multiple attendees acknowledged that most executive thought leadership efforts fail not because leaders lack expertise or strong ideas, but because publishing becomes inconsistent. Content slows down, competing priorities take over, and momentum disappears before audiences ever associate executives with a recognizable point of view.

Several participants shared practical ways to maintain consistency, including committing to one flagship content piece each week, repurposing ideas across multiple channels, and carrying themes through several formats instead of treating every post as standalone content.

The takeaway: thought leadership compounds over time. Repetition and sustained visibility build trust far more effectively than occasional bursts of activity.

4️⃣ The hardest part is translating expertise into narrative

One particularly interesting discussion centered around highly technical executives and the challenge of helping them communicate strategically instead of tactically. Several marketers described situations where CEOs defaulted into discussing product features and technical details instead of framing broader market narratives audiences could connect with.

For complex industries especially, attendees emphasized that executive thought leadership starts with translating what makes a company valuable into a clear and accessible narrative. Once that narrative exists, formats like podcasts, webinars, videos, and LinkedIn posts become much easier to execute consistently.

The takeaway: executives rarely lack expertise. The bigger challenge is helping them shape that expertise into stories and frameworks audiences can quickly understand and remember.

5️⃣ Authentic executive perspectives are becoming more valuable in the AI era

A broader undercurrent throughout the conversation was growing fatigue around low quality AI generated content and repetitive messaging. Several attendees pointed out that as more organizations automate content production, audiences are becoming increasingly sensitive to generic language and recycled insights.

That shift is making authentic executive thought leadership more valuable as a trust signal. Participants connected this directly to SEO, AEO, and discoverability trends, noting that buyers are increasingly looking for recognizable voices and real expertise instead of faceless brand content.

The takeaway: AI may accelerate content creation, but authentic human perspective is becoming a stronger differentiator. The companies building trust fastest are the ones consistently putting real expertise and recognizable voices into the market.

]]><![CDATA[Brian C. Reed: How Community Storytelling Builds Brands That Stand Out In The AI Era - Episode #47]]>https://www.connecttomarket.com/p/how-community-storytelling-builds-brands-in-the-ai-erahttps://www.connecttomarket.com/p/how-community-storytelling-builds-brands-in-the-ai-eraThu, 14 May 2026 09:01:47 GMTDoes AI make every brand sound exactly the same?

In this episode of Connect To Market, host Casey Cheshire sits down with Brian C. Reed, Chief Market Officer at Corsha and veteran B2B tech marketing executive, to explore why marketers who lean on AI for differentiation are actually flattening their messaging into sameness, and how authentic, human storytelling rooted in community is the real engine for memorability and brand preference. Reed makes the case that AI is essential for speed and analytics but cannot replace the kind of stories that come from, flow through, and are amplified by real communities, giving marketers a powerful framework to connect to their market in ways algorithms simply cannot replicate.

Reed walks through the sources of strong stories, from founder origin narratives to practitioner communities, drawing on examples ranging from Mad Men-era advertising and Steve Jobs’ MacBook Air launch to modern standouts like All Day DevOps, OWASP, and Wiz’s memorable RSA presence. He explains how community-led evangelism helps grow credibility, why communities fail when vendor pitching overwhelms peer value, and how organizations like CMO Coffee Talk and the Cybersecurity Marketing Society model authentic community building. Reed also shares his own career journey from engineering to product marketing and offers advice on learning business mechanics beyond building technology.

In this episode, we cover:

  • Why AI “flattens” marketing messaging into sameness and where human storytelling becomes the true competitive advantage

  • How to source authentic stories from founder origins and practitioner communities that build lasting brand preference

  • The three paths to community building and what separates vendor-proof communities from ones that collapse under self-promotion

  • Lessons from Reed’s engineering-to-marketer career arc on understanding business mechanics to become a more effective marketing leader

If you’re a B2B marketing leader wrestling with how to stand out when every competitor has access to the same AI tools, Reed’s community-first storytelling framework offers a differentiation playbook that no algorithm can copy.

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

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

]]><![CDATA[David Kosloski: Stop Prompting, Start Building AI Systems That Scale - Episode #46]]>https://www.connecttomarket.com/p/stop-prompting-start-building-ai-systemshttps://www.connecttomarket.com/p/stop-prompting-start-building-ai-systemsThu, 07 May 2026 09:00:44 GMTWhat if the real threat to your marketing isn’t falling behind on AI, but not having the systems to use it?

In this episode of Connect To Market, host Casey Cheshire sits down with David Kosloski, VP of Marketing at SNUC and host of the Edge Tech Podcast, to explore how marketers connect to their market by building experience, expertise, authority, and trust before chasing tools or tactics. David makes the case that in emerging categories like edge computing, relationships and problem-solution expertise consistently outperform product specs, and that the marketers who win are the ones who start with content and customer insight rather than keyword lists.

David walks through his approach to building authority in a new market, from launching podcasts and conducting customer interviews to creating mind maps and repurposing content across formats. He then dives into his perspective on AI, arguing that it won’t save teams that lack strong systems, management discipline, and the ability to pressure-test their own work. He shares his framework for agentic workflows, breaking down the difference between skills and agents, the importance of validation loops and structured data (RAG), and how voice-first input is reshaping his personal productivity. He also reflects on his unconventional path from touring music and healthcare into marketing leadership, and shares his take on AI’s impact on jobs and the SaaS landscape.

In this episode, we cover:

  • Why E-E-A-T (experience, expertise, authority, trust) matters more than product specs when marketing in emerging categories

  • How to build market authority from scratch using podcasts, customer interviews, and content repurposing

  • Why AI amplifies existing systems instead of replacing them, and how to build agentic workflows with validation loops

  • Using voice-first input and a “second brain” RAG approach to unlock personal productivity with AI

If you’re a B2B marketing leader navigating a new or technical category and wondering how to layer AI into your workflow without losing the human judgment that makes your marketing credible, David’s systems-first framework is the reality check you need.

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

]]><![CDATA[Aaron Bean: Arm Your Buyer Champion to Win CFO Approval - Episode #45]]>https://www.connecttomarket.com/p/arm-your-buyer-champion-to-win-cfo-approvalhttps://www.connecttomarket.com/p/arm-your-buyer-champion-to-win-cfo-approvalThu, 30 Apr 2026 09:01:37 GMTWhat if your biggest competitor isn’t another vendor, but your buyer’s fear of making the wrong decision?

In this episode of Connect To Market, host Casey Cheshire sits down with Aaron Bean, Co-Founder and Head of Go-to-Market at Supercase.ai, to explore why the most dangerous competitor in B2B isn’t a rival product, but buyer indecision. Aaron makes the case that marketers need to connect to their market by focusing on the late-stage buyer journey, equipping champions to win the internal sale in a room the seller will never be in, especially when the CFO starts asking what the problem is costing and why it can’t be fixed internally.

Aaron shares research showing 61% of deals are lost to indecision and breaks down the three options every buyer weighs: do nothing, build, or buy. He walks through a framework for building decision confidence by quantifying the cost of inaction, creating CFO-credible business cases, and mapping internal advocacy moments into the buyer journey. He also introduces tracking “business case attach rate” as a leading indicator of deal health, and shares lessons from his background in philosophy, entrepreneurship, and global go-to-market work at Lenovo.

In this episode, we cover:

  • Why 61% of B2B deals are lost to buyer indecision, not competitors, and how to fight back

  • How to arm buyer champions with CFO-credible business cases that quantify the cost of doing nothing

  • Adding internal advocacy moments to your buyer-journey map so champions aren’t left unsupported

  • Tracking “business case attach rate” as a leading indicator of deal confidence and close rates

If you’re a B2B marketing leader watching qualified deals stall in committee and losing to “no decision,” Aaron’s framework for building decision confidence and arming your buyer champions is the playbook you’ve been missing.

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

]]><![CDATA[Brandon Pittser: Drink Your Own Kool-Aid to Build Marketing That Converts - Episode #44]]>https://www.connecttomarket.com/p/brandon-pittser-drink-your-own-koolhttps://www.connecttomarket.com/p/brandon-pittser-drink-your-own-koolThu, 23 Apr 2026 13:05:20 GMTIs your marketing falling flat because you don’t actually believe in what you’re selling?

In this episode of Connect To Market, host Casey Cheshire sits down with Brandon Pittser, VP of Marketing and Funding Development at Filament Games, to explore how marketers can connect to their market by leading with authenticity instead of automation. Brandon makes the case that the most effective marketing starts with genuinely believing in your organization’s value, and explains why formulaic, AI-templated outreach is eroding trust with buyers. He shares why humility, honesty, and respecting your audience’s intelligence are the real competitive advantages in a landscape flooded with generic messaging.

Brandon walks through his playbook for internalizing a company’s story, from interviewing discipline leaders to synthesizing perspectives and aligning teams around core value. He then breaks down how Filament Games drives growth through a disciplined inbound content engine, including long-running SEO-driven blogging, a structured editorial calendar, and an expanding video strategy built around repurposing livestreams into short-form clips. He also shares how to build modular content campaigns, maintain editorial flexibility, and lean into your organization’s existing strengths to create content that compounds over time.

In this episode, we cover:

  • Why authentic belief in your product is the foundation of marketing that resonates and converts

  • How to align your team around a unified company story by interviewing internal leaders and synthesizing their perspectives

  • Building a disciplined inbound content engine with SEO-driven blogging and a flexible editorial calendar

  • Expanding into short-form video by repurposing livestreams and leaning into organizational strengths

If you’re a marketing leader tired of watching templated outreach fall flat and looking for a more genuine, sustainable approach to content and demand generation, Brandon’s framework for authentic, inbound-first marketing is one worth stealing.

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

]]><![CDATA[ABM Isn’t Broken… But It’s Definitely Misunderstood: Takeaways from our April CTM Event]]>https://www.connecttomarket.com/p/abm-isnt-broken-but-its-definitely-misunderstoodhttps://www.connecttomarket.com/p/abm-isnt-broken-but-its-definitely-misunderstoodMon, 20 Apr 2026 16:58:49 GMTLast week, our community tackled a topic that everyone claims to be doing, but few feel confident they are doing well: Account-Based Marketing. What started as a conversation about ABM quickly expanded into something bigger, how it overlaps with AEO, where AI fits and doesn’t, and whether the term ABM even still means anything. From philosophical debates to tactical experiments, marketing leaders unpacked what is working, what is overhyped, and where things are heading next.

💡 5 Key ABM + AEO Takeaways for Marketing Leaders

1️⃣ “Everything is ABM” is both true and completely unhelpful

Across discussions, one theme was clear: ABM has become too broad to be useful. Some leaders argued that all marketing is inherently account based, especially in B2B where audiences are niche by default. Others pushed back, pointing out that true ABM requires intentionality, defined target lists, tailored outreach, and coordinated sales alignment.

The takeaway: when everything is labeled ABM, nothing is differentiated. Teams need to be explicit about what kind of ABM they are actually executing, whether that is 1:1, 1:few, or industry based, or risk spinning in circles.

2️⃣ Personalization sounds great until you factor in cost, scale, and signal noise

There was broad agreement that 1:1 personalization can be powerful, but it is also complex, expensive, and often impractical. Several leaders called out the reality that most personalization today is still industry level at best, not truly account or individual specific. Layer in AI, and the challenge compounds. With so much low quality, AI generated outreach flooding the market, it is becoming harder to tell what actually resonates.

The takeaway: personalization only works when it is meaningful, and most teams overestimate their ability to execute it well at scale.

3️⃣ The biggest gap is not tools, it is target selection and focus

Across the board, teams are experimenting with tools like AI SDRs, intent data, and enrichment platforms, but many admitted their ABM programs still feel loose or uncoordinated. The consistent friction point is who to target and why. Some teams are working from tightly defined lists of 20 to 40 accounts, while others are casting wider nets without clear prioritization.

The takeaway: ABM success is less about better execution and more about sharper focus. If your target list is not right, nothing downstream will fix it.

4️⃣ AEO and ABM are not naturally aligned, yet

A recurring tension was that ABM is outbound and controlled, while AEO is inbound and unpredictable. Many leaders struggled to connect the two. That said, early experiments are emerging, including using AEO insights like prompts, queries, and visibility gaps to inform ABM messaging, identifying the conversations target accounts are likely having in AI tools, and feeding those insights into content and outreach strategies.

The takeaway: AEO is not replacing ABM, but it may become a critical input into how you prioritize and engage accounts.

5️⃣ AI is accelerating experimentation, but not replacing fundamentals

From building internal AEO scanners to testing AI appointment setters and chatbot driven outreach, teams are moving fast. But there was a clear reality check. AI can help with research, content, and scale, but it does not solve poor targeting, weak messaging, or lack of sales alignment. There was also skepticism around emerging areas like LLM advertising, where early signals suggest that without strong organic presence, paid placements in AI driven environments will not perform.

The takeaway: AI is a multiplier, not a strategy. The teams seeing traction are using it to enhance fundamentals, not shortcut them.

The through line: ABM has not failed, it has been overgeneralized, overpromised, and underdefined. When targeting is tighter, intent is clearer, and engagement is more thoughtful, ABM becomes more effective and better aligned to how buyers actually discover and evaluate solutions today.

]]><![CDATA[Max Maurier: Essential Marketing Adaptation Skills in the AI Age - Episode #43]]>https://www.connecttomarket.com/p/max-maurier-essential-marketing-adaptationhttps://www.connecttomarket.com/p/max-maurier-essential-marketing-adaptationThu, 16 Apr 2026 09:01:49 GMTHow can marketers stay adaptable, leverage AI effectively, and earn a true seat at the table?

In this episode of Connect To Market, host Casey Cheshire welcomes Max Maurier, VP of Marketing at Absolute Security, to explore why adaptability is the most critical skill for modern marketing teams. Max shares how marketing is uniquely positioned to pivot faster than other functions, and why leaders must continuously evolve their strategy, channel mix, and team capabilities in response to shifting buyer behavior, company priorities, and emerging technology.

He dives into the importance of aligning deeply with company-wide goals (not just reacting to sales requests), and how strong analytics and system fundamentals can help marketers build credibility and trust at the executive level. From rethinking event-heavy strategies to creating a more balanced, targeted digital approach, Max outlines what it takes to operate as a truly strategic marketing function. He also unpacks practical AI use cases, like account research and planning, while emphasizing the need to keep humans in the loop to avoid low-quality, “AI slop” outputs.

In this episode, we cover:

  • Why adaptability, not rigid planning, is the key to modern marketing success

  • How to align marketing with broader business objectives to increase impact and influence

  • Practical ways to apply AI across marketing teams without over-relying on it

  • How to use data, analytics, and systems to earn trust and a seat at the executive table

If you’re a marketing leader looking to stay ahead of constant change, better integrate AI, and elevate your role within the organization, Max’s insights will challenge how you think about strategy, execution, and leadership.

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

]]><![CDATA[Alex Schutte: 6 Ways To Drive Revenue & Earn Executive Trust - Episode #42]]>https://www.connecttomarket.com/p/alex-schutte-6-ways-to-drive-revenuehttps://www.connecttomarket.com/p/alex-schutte-6-ways-to-drive-revenueThu, 09 Apr 2026 09:01:47 GMTWhat if the fastest way to improve your marketing performance isn’t better messaging but better data?

In this episode of Connect To Market, host Casey Cheshire welcomes Alex Schutte, Senior Vice President of Marketing at Hubstaff, to explore how marketers can connect to their market by prioritizing data clarity before refining messaging. Alex explains why many B2B teams struggle with alignment and trust due to inconsistent definitions and fragmented reporting, and how fixing these foundational issues can unlock stronger decision making and revenue impact. He shares why marketers who lead with data, not just campaigns, are better positioned to earn executive trust and drive meaningful growth.

He breaks down how leaders can move from disconnected metrics to a unified, revenue driven strategy by standardizing key definitions across the funnel, building a centralized executive dashboard, and adopting a bow tie growth model that captures the full customer lifecycle. From analyzing top customers and segmenting effectively to operationalizing LTV and aligning spend accordingly, Alex outlines practical ways to turn data into a strategic advantage. He also touches on forecasting, attribution realities, and how to lead teams with clear expectations and unbiased insights.

In this episode, we cover:

  • Why data clarity is the foundation for effective go to market strategy

  • How to standardize definitions and build a single source of truth

  • Using a bow tie model to understand growth across the full customer lifecycle

  • Aligning marketing efforts to revenue and using LTV to guide smarter decisions

If you’re a marketing leader looking to improve performance, strengthen alignment, and build credibility with executives, Alex’s approach offers a clear roadmap for turning better data into better business outcomes.

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

]]><![CDATA[AEO Guide: We Need Your Brainpower]]>https://www.connecttomarket.com/p/we-need-your-brainpower-help-shapehttps://www.connecttomarket.com/p/we-need-your-brainpower-help-shapeWed, 08 Apr 2026 14:03:26 GMTAlright CTM… this is one of those moments where the magic of this community really shows up.

Over the past couple of months, one of our members, Ron Close, has been deep in the weeds on Answer Engine Optimization (AEO), testing, learning, and pulling together a practical guide to what’s actually working right now.

And instead of just publishing it and calling it done, he did something better.

He brought it here.

Because the truth is: the best ideas don’t come from one perspective, they come from rooms like this.

So we’re turning this into a community-powered review.

This is your chance to:

  • Pressure test the ideas

  • Add your own real-world experiences

  • Challenge assumptions

  • Sharpen what’s already here

  • And help shape something that could become a go-to resource for marketers navigating AEO

Whether you’re actively experimenting with AEO, just starting to explore it, or have strong opinions about where it’s headed, we want your feedback!

As you read, think about:

  • What made you pause or rethink something?

  • What feels spot on?

  • What’s missing?

  • Where would you push this further?

Download the guide below and drop your thoughts in the comments, react to others, build on ideas!

Aeo Guide V2
552KB ∙ PDF file
Download
Download

]]><![CDATA[Melissa Moody: Concentric Circles, Empowering Teams & Customer Success as Marketing - Episode #41]]>https://www.connecttomarket.com/p/melissa-moody-concentric-circleshttps://www.connecttomarket.com/p/melissa-moody-concentric-circlesThu, 02 Apr 2026 09:02:34 GMTWhat if your most powerful growth strategy isn’t reaching more people, but starting with the ones closest to you?

In this episode of Connect To Market, host Casey Cheshire welcomes Melissa Moody, Founder of Wednesday Women and Host of the Joy of Connecting podcast, to explore how brands can drive growth by returning to authentic human relationships. Melissa introduces her “concentric circles of 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.

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

]]><![CDATA[Ian Dowe: Building a Solid Foundation, Embracing Creativity & Data-Driven Decisions - Episode #40]]>https://www.connecttomarket.com/p/ian-dowe-building-a-solid-foundationhttps://www.connecttomarket.com/p/ian-dowe-building-a-solid-foundationThu, 26 Mar 2026 09:02:33 GMTHow can B2B SaaS companies build a strong go-to-market foundation and turn their website into a true driver of pipeline?

In this episode of Connect To Market, host Casey Cheshire welcomes Ian Dowe, Senior Vice President Marketing at HealthAxis, to explore how marketers can connect to their market through a deeply data-driven foundation. Ian explains why understanding your total addressable market, 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.

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

]]><![CDATA[Why Most Trade Show ROI Falls Flat: Takeaways from our March CTM Event]]>https://www.connecttomarket.com/p/why-most-trade-show-roi-falls-flathttps://www.connecttomarket.com/p/why-most-trade-show-roi-falls-flatTue, 24 Mar 2026 13:30:11 GMTLast week, our community dug into a challenge many teams feel but struggle to quantify: trade shows are expensive, high-effort, and often unclear in impact. From booth design critiques to lead qualification strategies, marketing leaders across industries unpacked what actually drives ROI on the show floor… and what quietly drains it.

💡 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.

]]><![CDATA[Trade Show ROI - Post-Event Panel - March 19, 2026]]>https://www.connecttomarket.com/p/trade-show-roi-post-event-panel-marchhttps://www.connecttomarket.com/p/trade-show-roi-post-event-panel-marchTue, 24 Mar 2026 13:27:02 GMTIf you missed the recent CTM: Growth Roundtable, you missed a focused conversation on maximizing Trade Show ROI through smarter booth strategy, stronger in-person engagement, and a clearer connection between event activity and pipeline, but we made sure to capture the most valuable takeaways in our post-session discussion.

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!

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

]]><![CDATA[Bill Kenney: Trade Show ROI - Lightning Speaker - March 19, 2026]]>https://www.connecttomarket.com/p/bill-kenney-trade-show-roi-lightninghttps://www.connecttomarket.com/p/bill-kenney-trade-show-roi-lightningTue, 24 Mar 2026 13:22:06 GMTHow can marketers assess trade show booth effectiveness and attract the right prospects instead of just the crowd?

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!

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

]]><![CDATA[Bill Kenney: Trade Show Masterclass - Episode #39]]>https://www.connecttomarket.com/p/bill-kenney-trade-show-masterclasshttps://www.connecttomarket.com/p/bill-kenney-trade-show-masterclassThu, 19 Mar 2026 09:01:23 GMTHow can booth design and messaging transform your trade show results?

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

Bill breaks down why 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!

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

]]><![CDATA[Angela Earl: Honest Conversations, Moving Feedback Through Teams & Using Real Signals - Episode #38]]>https://www.connecttomarket.com/p/angela-earl-honest-conversationshttps://www.connecttomarket.com/p/angela-earl-honest-conversationsThu, 12 Mar 2026 09:02:21 GMTHow can marketers better connect with their market when customer insights are often filtered, polished, or stuck in silos?

In this episode of Connect To Market, host Casey Cheshire welcomes B2B GTM Leader Angela Earl to explore how organizations can strengthen their connection to customers by listening more closely- not just to feedback, but to the real conversations happening across their teams. 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.

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

]]><![CDATA[Valerie Zargarpur: Crafting Brand Stories & Cybersecurity Differentiation - Episode #37]]>https://www.connecttomarket.com/p/valerie-zargarpur-crafting-brandhttps://www.connecttomarket.com/p/valerie-zargarpur-crafting-brandThu, 05 Mar 2026 10:01:29 GMTHow can B2B brands win discovery, trust, and positioning when most cybersecurity messaging blends together?

In this episode of Connect To Market, host Casey Cheshire welcomes Valerie Zargarpur, Head of Marketing at Monad, to explore how marketers can connect to their market through brand story rather than just visual identity. Valerie explains why B2B, especially cybersecurity, often relies on 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:

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

]]><![CDATA[John Rougeux: Category Strategy, Inflection Points & Executive Alignment - Episode #36]]>https://www.connecttomarket.com/p/john-rougeux-category-strategy-inflectionhttps://www.connecttomarket.com/p/john-rougeux-category-strategy-inflectionThu, 26 Feb 2026 10:01:33 GMTHow can marketers escape the tactics trap and build category strategy that actually connects to the market?

In this episode of Connect To Market, host Casey Cheshire welcomes John Rougeux, Founder of Flag & Frontier, to unpack why marketers are often set up for failure when they’re handed KPIs without influence over strategy. John argues that real market connection starts with understanding the category, buyer environment, and problem maturity - not chasing isolated tactics. Using a race car analogy, he explains why fundamentals matter more than surface-level optimization and how marketing becomes powerful when it shapes direction, not just execution.

John outlines three core pillars: first, aligning on the real problem and who it’s for by talking directly to customers; second, assessing the maturity of that problem to determine whether to create a category, carve out a niche in a mature market, or reinforce leadership like Salesforce; and third, distilling strategy into a clear narrative that aligns internal teams and guides external messaging. Drawing a parallel to a trial lawyer’s structured argument, he explains how strong strategy blends logic and emotion to move markets. He also shares lessons from his path from finance to performance marketing to advising companies at strategic inflection points, including examples like how Zoom reinvigorated a crowded space.

In this episode, we cover:

  • Why marketers get trapped in tactics without strategic 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:

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  • Spotify:

  • Apple Podcasts:

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

]]><![CDATA[Message Market Fit Masterclass - Post-Event Panel - February 19, 2026]]>https://www.connecttomarket.com/p/message-market-fit-masterclass-posthttps://www.connecttomarket.com/p/message-market-fit-masterclass-postTue, 24 Feb 2026 10:02:46 GMTIf you missed the recent CTM: Growth Roundtable, you missed a sharp conversation on connecting messaging to pipeline through ICP playbooks, jobs-to-be-done, and disciplined customer research, but we made sure to capture the most valuable takeaways in our post-session discussion.

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/

]]><![CDATA[Chris Silvestri: Message Market Fit Masterclass - Lightning Speaker - February 19, 2026]]>https://www.connecttomarket.com/p/chris-silvestri-message-market-fithttps://www.connecttomarket.com/p/chris-silvestri-message-market-fitTue, 24 Feb 2026 10:02:29 GMTHow can marketers achieve true message-market fit and stop fixing the wrong layer when conversion drops?

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/

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