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.
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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/
