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#62

How to Build an AI-Powered ABM Strategy: Elyssa Steiner - Episode #62

What if the fastest way to master nine marketing verticals isn't a better dashboard, but getting your team out from behind their desks? In this episode of Connect To Market, host Casey Cheshire sits down with Elyssa Steiner, CMO of Kahua, to explore how B2B marketing leaders can build stronger buyer connection through a mix of field research and AI-driven execution. Elyssa makes the case that AI can scale what you already know, but it can't invent what you haven't learned yet, and that field visits, sales call shadowing, and trade show attendance are what turn AI-synthesized data into real buyer insight. She shares how she used her first 60 days as CMO to build ideal customer profile (ICP) frameworks for nine core verticals, why she sends a marketer to every trade show her company exhibits at, and how listening in on sales calls became one of the highest-value habits on her team. Elyssa walks through how Kahua's AI adoption evolved from basic custom GPTs to purpose-built AI skills and an account-based marketing (ABM) agent that scaled the team's target account list from a capacity-constrained "Magic 18" to more than 400 one-to-one and one-to-few accounts. She breaks down why she believes the most critical skill for a modern marketer is being a really good editor, not a really fast prompter, and how her team is shifting from repetitive execution work into real marketing strategy as AI takes over the busy work. She also opens up about her own career path from retail buying to startup sales to CMO, and the philosophy that has shaped her decision-making ever since: hard choices, easy life; easy choices, hard life. In this episode, we cover: Why closing the physical distance between marketing and the buyer, not just better AI tools, is what actually builds buyer understanding How to build ICP frameworks for multiple verticals in your first 60 days and turn that work into a springboard for AI tools and content strategy How to scale an ABM strategy from a handful of target accounts to hundreds once AI takes the busy work off your team's plate Why "don't let comfort make your decisions" is the throughline for marketing leaders moving from individual contributor to CMO If you're a marketing leader trying to figure out how AI actually fits into your team's workflow without losing the human judgment that makes marketing work, Elyssa's approach to pairing field experience with AI-powered execution is the playbook you've been missing. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Elyssa: LinkedIn: https://www.linkedin.com/in/elyssasteiner/ Ways to Tune In: Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920 Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d iHeart Radio: https://iheart.com/podcast/282837141/ Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391 YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV More About Elyssa:  Elyssa Steiner is Chief Marketing Officer at Kahua and a B2B growth leader with more than 15 years of experience building brands, leading high-performing teams, and developing integrated marketing strategies that drive pipeline, customer engagement, and measurable business growth. At Kahua, she leads the company’s marketing vision and go-to-market strategy across brand, demand generation, product marketing, customer advocacy, and marketing operations. She is also advancing an AI-fluent approach to marketing, using AI to uncover insights, scale execution, and improve efficiency while keeping strategy, creativity, and customer understanding at the center. Before joining Kahua, Elyssa served as Chief Marketing Officer at Cantaloupe, where she helped guide the company through a period of significant growth and transformation. During her final two years, Cantaloupe grew annual recurring revenue from approximately $250 million to $310 million while she led marketing through multiple acquisitions, portfolio and brand integration, and the company’s eventual sale. Her expertise spans revenue-driven marketing, go-to-market strategy, sales alignment, customer growth, fintech, and emerging technology. She has shared her perspective on The Revenue-Driven CMO, multiple Leaders in Payments episodes, and a live Marketing on Mars CMO panel in San Francisco. Elyssa holds a master’s degree in Communication and Leadership from Gonzaga University and a bachelor’s degree in Business and Marketing from the University of Washington. Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/
#61

Scaling Client Relationships Through Community: Paul Jones - Episode #61 (Re-Air)

What does it take to build authentic communities that truly connect with your market? In this episode of Connect to Market, host Casey Cheshire welcomes Paul Jones, Moderator of the Connect To Market Community & Founder of Bridgio. Paul shares lessons from building over 40 successful communities and explains why real market connection goes beyond launching products or campaigns. He emphasizes the importance of deeply understanding your Ideal Client Persona (ICP), using empathy to craft resonant messaging, and creating space for meaningful, value-driven interactions. Paul also challenges the overreliance on technology, encouraging marketers to start simple and stay focused on human connection. In this episode, we cover: The difference between going to market and connecting to it How to understand your ICP beyond the surface level Why low-tech, high-value engagement builds stronger communities Real examples of community-led product and messaging success If you're looking to engage your audience more meaningfully and build communities that drive real connection, this episode offers practical and inspiring insights. 🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Paul: LinkedIn: https://www.linkedin.com/in/pauljones101/   Bridgio: https://bridgio.io/  Ways to Tune In: Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa  Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920  Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d  iHeart Radio: https://iheart.com/podcast/282837141/  Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391  YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 
#60

Turning Live Events into Podcast Magic: Casey Cheshire - Episode # 60

What happens when you take a podcast out of the studio and bring it into the middle of a live event? In this special edition of Connect To Market, host Casey Cheshire joins us live from Las Vegas and the Ringmaster Mobile Podcast Studio at Black Hat to share why live events and podcasts can be such a powerful combination for B2B marketers. In between recordings, Casey breaks down how brands can use podcasting to create more human connection, generate buzz around an event, turn conversations into content, and build stronger relationships with prospects and customers. Casey shares some of the conversations he’s had with members of the Connect To Market community at Black Hat, including discussions around AI, growth, happiness, and the importance of maintaining a human balance in an increasingly noisy digital world. He also walks through several practical ways to bring a podcast to your next event, from capturing quick “hot takes” to using podcast conversations as a reason for prospects to show up for meetings. The episode also explores how live podcasting can create more authentic customer stories, strengthen relationships, and surface the thought leadership already sitting inside your organization. Casey’s takeaway? As AI-generated content and digital noise continue to increase, genuine human connection becomes even more valuable. In this episode, we cover: Why live events and podcasts can create a powerful combination for human connection How to use quick “hot takes” to generate buzz and turn event conversations into podcast content Why podcast interviews can give prospects a better reason to show up for meetings How AI and content “slop” are making human connection more important than ever If you're heading to a conference or planning your next live event, Casey's playbook offers simple ways to turn the conversations happening around you into meaningful relationships, content, and opportunities. 🔔 Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Casey: LinkedIn: linkedin.com/in/caseycheshire  Website: ringmaster.com  Ways to Tune In: Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa  Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920  Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d  iHeart Radio: https://iheart.com/podcast/282837141/  Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391  YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 
#59

The AI Prompting Masterclass Every Marketer Needs To Hear: Keven Ellison - Episode #59 (RE-AIR)

How can marketers harness AI to boost productivity and innovation without losing the human expertise that drives real results? In this episode of Connect To Market, host Casey Cheshire welcomes Keven Ellison, Vice President of Marketing at A.I.S., to explore how AI is transforming marketing, content creation, and business systems while still honoring the experience and strategy that drive real results. Keven discusses the rapid advancements in AI and why being proficient in AI is essential for marketers to stay relevant. He shares his journey of learning to prompt effectively and building AI workflows that have drastically increased productivity. The opportunity lies in using AI to scale strategically while keeping messaging aligned with what truly matters to buyers. He shares why marketers must guide AI tools like a new team member by equipping them with brand knowledge, audience insights, and clear instructions to ensure quality and consistency. From building strong workflows to creating human feedback loops, Keven explains how marketers can accelerate content creation without sacrificing strategy or creativity. He also highlights the future of AI in organizations, predicting the transformation of traditional CRMs and human resource departments into AI-driven systems, and emphasizes the need for marketers to adopt and adapt to AI technologies to lead effectively. In this episode, we cover: Why marketers must stay ahead of AI trends to remain competitive How to master AI prompts and build scalable workflows How AI is changing the future of work, including CRM and HR systems Why human creativity and business experience remain essential If you’re a marketing leader looking to leverage AI while strengthening your strategy and creativity, Keven’s insights provide a smart, practical path to modern marketing success. 🔔 Don’t forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Keven: LinkedIn: https://www.linkedin.com/in/kevenellison   AIS-NOW: https://www.ais-now.com/  PromptMaster XL 1.2: https://chatgpt.com/g/g-682a348e1f7c8191a11cd42dda5f9ff3-promptmaster-xl-1-2  Image Prompt Architect: https://chatgpt.com/g/g-682bbe0333f48191aa6521a6cbf93958-image-prompt-architect Ways to Tune In: Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa  Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920  Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d  iHeart Radio: https://iheart.com/podcast/282837141/  Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391  YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ 
#58

The Pipeline Wake-Up Call Every B2B Marketer Needs to Hear: Randy Brasche - Episode #58

What if the reason marketing keeps getting sidelined is because marketers are measuring the wrong things? In this episode of Connect To Market, host Casey Cheshire sits down with Randy Brasche, Chief Revenue Officer at Spot-On, Principal at Adaptive B2B Solutions, and author of "Some Assembly Required," to explore how marketers can connect to their market by getting close to revenue rather than hiding behind conversions and volume metrics. Brasche argues that marketers must understand pipeline coverage multiples, participate in pipeline calls with confidence, and build strategy around ICP definition, account engagement, and the full customer lifecycle, not just top-of-funnel lead generation. He makes the case that the marketers who earn a seat at the revenue table are the ones who can speak the language of pipeline math and tie their work directly to acceleration, churn reduction, and expansion. Brasche walks through why most marketers default to volume and conversion metrics that don't resonate with revenue leaders, and how shifting focus to pipeline multiples and lifecycle engagement changes the entire conversation. He breaks down the math behind pipeline coverage, explains how to identify the 10 percent of your market that is actually in-market at any given time, and shares how intent data and ICP refinement can sharpen targeting. The conversation also dives into the AI balance: Brasche outlines how AI can improve ICP definition, context delivery, and messaging quality at scale, but warns that data cleanliness and human oversight are non-negotiable for accuracy.  In this episode, we cover: Why marketers must learn pipeline coverage math and participate in pipeline calls to earn credibility with revenue leaders How to move beyond volume and conversion metrics to focus on lifecycle engagement, churn reduction, and expansion Using AI to sharpen ICP definition and deliver context at scale while maintaining data cleanliness and human oversight Why personal agency, confidence, and conviction are the most important traits for marketers in the AI era If you're a marketing leader who feels disconnected from revenue conversations or unsure how to prove your impact beyond MQLs and conversion rates, Brasche's pipeline-math framework and revenue-proximity mindset is the playbook you need to change the conversation. đź”” Don't forget to subscribe and hit the notification bell so you never miss an episode of Connect To Market. Connect with Randy: LinkedIn: https://www.linkedin.com/in/rbrasche/  Spot-On: https://spot-on.com/  Adaptive B2B: https://adaptiveb2b.com/  Some Assembly Required Book: https://www.amazon.com/dp/B0FJZDXZCK  Ways to Tune In: Spotify: https://open.spotify.com/show/01kCcPP1ib9MSE9aNb5SQa  Apple Podcasts: https://podcasts.apple.com/podcast/connect-to-market/id1822777920  Amazon Music: https://music.amazon.com/podcasts/b5c3fb03-482f-4496-bcd0-82c1d66fed3d  iHeart Radio: https://iheart.com/podcast/282837141/  Podchaser: https://www.podchaser.com/podcasts/connect-to-market-6138391  YouTube: https://www.youtube.com/playlist?list=PLP_sn6_Cwun_qxaOz94Epgf6zdqeTFjJV  Connect To Market is produced and sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/Â