How can marketers break old habits and innovate to create meaningful B2B buyer experiences?

In this episode of Connect To Market, host Casey Cheshire sits down with Jennifer Cortez, Chief Marketing Officer of Alkami Technology, to explore how innovative marketing strategies can create real value and move beyond outdated practices. Jennifer shares her perspectives as a SaaS marketing expert, emphasizing the importance of personalized approaches, a culture of experimentation, and leveraging data and AI for smarter decision-making.

Jennifer provides practical insights on rethinking traditional marketing tools, crafting content that resonates, and embracing the evolving buyer’s journey. She discusses the significance of mentorship, taking calculated risks, and fostering a marketing culture that continuously innovates. Through real-world examples, Jennifer highlights how leaders can create meaningful buyer experiences while staying ahead of the curve in an increasingly competitive market.

In this episode, we cover:

• Why marketing the way you want to be marketed to leads to stronger buyer connections
• How to balance personalization, content strategy, and data-driven decision-making
• The role of AI and innovation in shaping the future of B2B marketing
• Why embracing change, mentorship, and risk-taking is critical for growth

If you’re a marketing leader looking to break away from “dinosaur” practices, elevate your strategies, and create experiences that truly engage buyers, Jennifer’s insights provide an actionable roadmap for 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 Jennifer:

• LinkedIn: https://www.linkedin.com/in/jenniferncortez/
• Alkami Technology: https://www.alkami.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/

What does it take for marketers to truly connect with their audience and harness AI for impactful strategies?

In this episode of Connect to Market, host Casey Cheshire welcomes Megan Ward, SVP of Marketing and Product Management at 360Factors. Megan offers a thoughtful and tactical breakdown of how marketers can deepen their understanding of target audiences by engaging directly and using AI-driven insights.

She shares why marketing leaders must spend time with “real people” to uncover authentic needs, the importance of attending industry events for firsthand market observation, and how AI analysis of call recordings can reveal key customer questions and concerns. Megan also reflects on her career journey and the lessons that helped her overcome limiting beliefs.

Throughout the conversation, Megan highlights actionable insights on connecting with customers, harnessing AI for smarter marketing, and documenting knowledge to empower teams.

In this episode, we cover:

• The importance of engaging directly with your target market
• Using AI to analyze customer interactions and extract insights
• The future of AI in marketing: digital agents and personalized tools
• The critical role of documenting and sharing knowledge within teams

If you're looking to build deeper market connections and integrate AI thoughtfully into your marketing, Megan’s insights provide a practical guide for leaders ready to innovate and lead with empathy.

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

Connect with Megan:

• LinkedIn: https://www.linkedin.com/in/radiantmegan/
• Substack: https://substack.com/@meganward989011
• 360factors: https://www.360factors.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/

What happens when we slow down and lead with gratitude in a fast-moving, pressure-filled marketing world?

In this special holiday episode of Connect To Market, host Casey Cheshire goes solo to reflect on the power of gratitude and why expressing it, openly and excessively, matters more than ever. Without a guest, Casey shares a heartfelt message of thanks to listeners, fellow marketers, and the team behind the show, creating space for presence, appreciation, and connection during the holiday season.

Casey explores how gratitude can shift perspective, ease anxiety, and reduce fear and frustration, especially during moments of uncertainty or burnout. Drawing inspiration from voices like Jay Shetty, Robert Holden, and Gertrude Stein, he highlights how gratitude fosters abundance, peace, and a deeper sense of awareness in both work and life. This episode serves as a reminder that gratitude isn’t passive, it’s a practice that can transform how we show up for ourselves and others.

In this episode, we cover:

• Why gratitude is a powerful tool for reducing anxiety and stress
• How expressing appreciation creates presence, peace, and perspective
• Quotes and reflections that reframe gratitude as an active practice
• Why now is the perfect time to pause, reflect, and say thank you

If you’re closing out the year feeling stretched, reflective, or hopeful for what’s ahead, this episode offers a meaningful pause, and an invitation to carry gratitude with you into the new year.

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

Connect with Casey:

• LinkedIn: https://www.linkedin.com/in/caseycheshire/
• Ringmaster: 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/