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Explore every episode of Best Story Wins

Dive into the complete episode list for Best Story Wins. Each episode is cataloged with detailed descriptions, making it easy to find and explore specific topics. Keep track of all episodes from your favorite podcast and never miss a moment of insightful content.

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Pub. DateTitleDuration
30 Mar 2023Ep. 1 Bryan Saftler (Director of Product Marketing - Communications, Media & Entertainment Industries at Databricks)00:50:13
Imagine taking three-decade-old technologies and making them work harder today, by combining the best of both data warehousing and data lake, making it easier to read and be more efficient. That’s the world that Bryan Saftler, Director of Product Marketing - Communications, Media & Entertainment Industries at Databricks, is helping to build. Bryan touches on the storytelling that is most compelling, the power of empathy in marketing, and the challenge of shaping narratives that speak to people at different levels, from the highest-order story to the individual use case. The conversation also touches on the role of AI and how marketers need to find ways to add value that cannot be easily replaced by it.

Join us as we discuss:
  • When it’s most important to gather feedback from early adopters to understand what is working and what isn't
  • Why it’s important to bridge the connection between the C-level executive and the individual use case when communicating the value of a product or service
  • How Databricks communicates the value of their platform to business decision makers and C-level executives
08 Mar 2023Introducing Best Story Wins00:00:34
Building and marketing a brand doesn’t always come naturally. Sometimes, you need to take a step back and see the bigger picture before diving into the details.

On the show, we connect with brand and marketing experts who have been through the difficult journey of driving real business results. We’ll also give you tips for turning ideas into conversions with some of today’s fastest growing companies.

You can find us on Apple, Spotify, or wherever you get your podcasts. Just search for “Best Story Wins,” and if you like what you hear, hit subscribe.

https://www.columnfivemedia.com/
27 Apr 2023Ep. 3 Keith Messick (CMO at LaunchDarkly)00:50:52
The tools B2B marketers rely on may be ever-evolving — whether that’s the channels they use, the data they collect or the technology they rely on — but the key to success in B2B is actually one overlooked element: Emotion.
In this episode of Best Story Wins, we speak with master storyteller Keith Messick, CMO at LaunchDarkly, about how he combines his knack for storytelling with all the tools, tactics, and strategies in modern marketing to tailor the perfect message for his ICP.
We discuss:
  • What B2B marketers can learn from B2C
  • When to use emotion and logic in your B2B marketing
  • How to stand out in your market
13 Apr 2023Ep. 2 Michelle Kim (Vice President of Brand Design at VideoAmp)00:48:33
The creatives at VideoAmp are risk takers — game changers. They have a level of ambition and drive that can’t be bought or taught, and it’s driving innovation throughout the industry.
On this episode of Best Story Wins, we speak with Michelle Kim, Vice President of Brand Design at VideoAmp. According to Michelle, the secret to cutting-edge culture is brand storytelling and company-wide alignment. From carefully tailoring the onboarding process to ensuring open avenues of honest communication, Michelle dives into what it takes to build an impactful brand story from the inside out.
Join us as we discuss:
  • How to define your brand story and what storytelling really means
  • Empowering your team to show up with purpose
  • What volatile times mean for innovation prioritization
25 May 2023Ep. 5 Devin Zimmerman (VP of Brand at Greenlight)00:47:45
By the time most people reach the age of 18, they’ve already had to make some huge financial decisions.

But how many young adults come into these decisions armed with a robust financial education?

Not enough says our latest guest, Devin Zimmerman. As VP of Brand at Greenlight, he’s helping to change that and joins the show today to share how.

Join us as we discuss:
  • How Greenlight is helping provide financial education for tweens and teens
  • How to understand branding trends for youths
  • How brands can find their own unique differentiators and why they must experiment to survive
11 May 2023Ep. 4 Drew Hoffman (VP of Brand at SentinelOne)00:56:47
One of the worst things you can do as a marketer is rely on outdated clichés. Unfortunately, it still happens all the time — so much so we all know the tropes.

In this episode, we’re speaking with Drew Hoffman, VP of Brand at SentinelOne, a cybersecurity company. Drew talks about the use of AI and how they’ve leveraged it to share their story in a new world.

Join us as we discuss:
  • How to capture the right emotion in your brand storytelling
  • How to leverage ai to build the brand
  • How Drew moved beyond the stale tropes to tell a unique cybersecurity story
  • Why cybersecurity tends to play it safe in its brand storytelling — and why that’s a mistake
20 Jul 2023Ep. 9 David Garvin (Creative Director at Happy Money)00:49:07
Today’s special guest is David Garvin, Creative Director at Happy Money. On this episode, we chat about how Happy Money infuses psychology into their branding and marketing, David’s philosophies on great storytelling, and how brands get it wrong. We also discuss future applications for AI in marketing, including how people’s desire for authenticity will continue to challenge the world of AI.

Join us as we discuss:
  • What the evolution of brand design for Happy Money looked like
  • How to handle a new CMO coming in with potential changes to the brand
  • When regulations will be put in place to address the ethical considerations of AI in the creative industry
08 Jun 2023Ep. 6 Jascha Kaykas-Wolff (President of Lytics)00:44:26
Are you ready to unlock your career's full potential? What if you could also align your passions, strengths, and aspirations for success using something called the Heart Tree Star?

Jascha Kaykas-Wolff, President at Lytics, delves into the key principles of career growth and leadership. By practicing empathy and understanding, leaders can reduce noise and tailor their messages to better connect with their audience, ultimately enhancing their own effectiveness and team engagement.

Tune in to discover how this powerful model can help you unlock your career potential, and bring your personal goals and professional growth together as you craft a compelling personal brand narrative. Join us as we discuss:
  • What the Heart Tree Star is and how can it guide career development
  • Why empathy is crucial in leadership positions for effective communication and collaboration
  • How people can take stock of their passions and skills to align them with their career path
22 Jun 2023Ep 7. Zach Kitschke (CMO at Canva)00:44:56
Today we’re talking with Zach Kitschke, CMO at Canva—one of the most impressive and disruptive companies around. Their mission is to empower everyone in the world to design anything and publish anywhere, and they are successfully doing it one user at a time. But being at the forefront of design and tech comes with its own challenges, as the need to innovate requires plenty of creative brainpower.

We chat with Zach about the intersection of artificial intelligence and creativity, how AI can serve as a co-pilot for human designers (by enhancing their creative process rather than replacing them), and how Canva is bringing AI into the fold with functionalities like Magic Design and Magic Words. From photo editing to generating copy ideas and translating content into multiple languages, the integration of AI into the creative process offers exciting possibilities for innovation and expanded creative expression.

Join us as we discuss:
  • The key features of Canva's AI-powered solutions
  • Why AI collaboration is crucial for enhancing human creativity in design
  • How Canva is addressing the challenges of maintaining brand integrity while creating content at scale
06 Jul 2023Ep. 8 Jackie Wylie (Chief Marketing Officer at Textio)00:54:27
Today we’re talking with Jackie Wylie, Chief Marketing Officer at Textio—a B2B SaaS company that makes workplaces more equitable, inclusive, and diverse by helping customers achieve measurable Diversity, Equity, and Inclusion (DEI) outcomes. On a mission to eliminate bias with both hiring and retention efforts, Textio is set to disrupt the way companies attract and retain talent.

We chat with Jackie about systemic bias in companies, how her team approaches storytelling around their DEI tools, the consequences of brands not pursuing DEI once the economy rebounds, and why DEI is still among the first things to be cut from budgets.

Join us as we discuss:
  • How language and rhetoric play a role in eliminating systemic bias
  • Software as an automation tool to help address systemic DEI issues in the workplace
  • Making the case for budget spend (even in today’s economy)
17 Aug 2023Ep. 11 Jonah Freedman (Content & Growth Marketing Leader at Salesforce)00:45:16
In this episode, we speak with Jonah Freedman, Content & Growth Marketing Leader at Salesforce. Tune in to hear Jonah share his journalistic approach to content marketing, where he finds inspiration, how he juggles different stakeholders, as well as his thoughts on the future of AI.

Join us as we discuss:
  • The key to both storytelling and content creation
  • How finding creative inspiration everywhere is powerful
  • Why AI has the potential to revolutionize content creation
31 Aug 2023Ep. 12 Ross Yoshida (Senior Director of Graphic Design for the Los Angeles Dodgers)00:44:35
Today’s special guest is Ross Yoshida, Senior Director of Graphic Design for the Los Angeles Dodgers. In this episode, we dive into how a blend of authenticity, confidence, and “hot sauce” has created one of the world’s most iconic sports brands. Tune in to hear Yoshida’s perspective on how winning brands elevate the fan experience, how the Dodgers’ creative team approaches each year’s visual campaign, where he gets his inspiration from, and more.

Just us as we discuss:
  • Challenging perspectives if your industry is stuck in the past
  • The fight to show that creative departments can be revenue generators
  • How visual branding deepens your connection with your audience
03 Aug 2023Ep 10. Ethan Kanat (Senior Creative Principal at Zendesk)00:50:33
Today’s special guest is Ethan Kanat, Senior Principal of Creative Strategy at Zendesk. In this episode, we dive into the biggest changes in tech and business in recent years, including the increasing importance of incorporating a strong narrative company-wide. As organizations are built with many individuals, human stories remain more important than ever. We cover how to use those stories as a foundation to build frictionless customer and employee experiences.

Join us as we discuss:
  • Zendesk’s perspective on remote work (and the role tech plays)
  • The importance of constantly telling your story, and how to incorporate a strong narrative throughout
  • How to build inspiration for great culture and good material, and whether AI can play a role
28 Sep 2023Ep. 14 Justin Rands (Director of Brand Design at Oyster)00:54:51
In this episode, we’re delighted to welcome in Justin Rands, Director of Brand Design at Oyster. Tune in to hear us chat about how he and his team make Oyster stand out as a brand, the importance of experimentation, the future of AI in content creation, and more. Justin also shares insights from his career journey, including the challenges of running a 700-person team and the riskiest moves he’s made at Oyster.

Join us as we discuss:
  • How the best brand stories find the human element
  • Why it’s so difficult to make creative that stops you in your tracks
  • The communication mistakes that are so costly for brands
12 Oct 2023Ep. 15 Joel Beukelman (Product Designer at Royal.io)01:00:27
In this episode, we have the pleasure of chatting with Joel Beukelman, Product Designer at Royal.io. Join us for a cutting-edge conversation in which Joel discusses what it’s like to build a marketplace at the intersection of cryptocurrency, music streaming, and Web3. With the goal of disrupting traditional, outdated practices in the music industry, Joel and his colleagues are designing solutions and tools that are aimed at empowering artists to connect with fans and monetize their music.

Join us as we discuss:
  • How technology can solve issues of unauthorized use of creative content
  • What collaboration requires: curiosity, flexibility, risk-taking, and a willingness to learn
  • Why humility and adaptability are critical in the startup world and crypto market
26 Oct 2023Ep. 16 Cymone Wilder (Senior Art Director, Brand at Amazon Web Services)00:46:05
Every brand needs a compelling story—even ones as established as Amazon Web Services.

Now it’s up to Cymone Wilder, Senior Art Director at Amazon Web Services, to rebuild the brand of an long-standing division that’s lacked a design focus for years. In this episode, Cymone shares lessons she’s learned from working at a company as big as AWS, such as dealing with tension that results from authenticity, initiating change at a large organization, and connecting with end users.

Join us as discuss:
  • Ambitious plans to shape the company's culture
  • The need to fake confidence (and why it doesn’t last)
  • Being scrappy and doing good work with what’s available
14 Sep 2023Ep. 13 Mike Constantiner (Co-Founder, Head of Brand and Community at Freestyle)01:00:24
In this episode, we are joined by Mike Constantiner, Co-Founder and Head of Brand and Community at Freestyle, the first brand in the market to manufacture tree-free baby diapers. As we delve into the process of ideation, consolidation, and maintenance of the company, Mike emphasizes the importance of building a narrative where the community—in this case, parents—hold the guiding voice that steers the brand's decisions to resonate with a wider audience and that can lead to the creation of a lifestyle brand. Additionally, Mike provides insights into the challenges, errors, and learnings that this process has imparted to him and his company, while also delving into their philosophy of "make cool shit" to maintain long-term relevance in the market.

Join us as we discuss:
  • Remaining competitive with limited time, talent and capital
  • The power of continuously making cool stuff, and finding the right team to do it
  • How crafting and building a great brand story can change the game for your company
09 Nov 2023Ep. 17 Joshua Ariza (Founder and Owner of Chomp Brand)00:52:28
Storytelling can be approached from various perspectives, and sometimes, exploring the less conventional ones can lead to the creation of a remarkable brand story.

Embracing an ethos-driven approach to storytelling is what today’s guest, Joshua Ariza, Founder and Owner of Chomp Brand, has done to tackle the complexities of building his own illustration label. Through the intersection of art and fun, Joshua shares insights into the benefits of having an expansive interpretation of the illustration marketplace, as well as the challenges that an economy in flux holds for the design industry.

Join us as we discuss:
  • Honing the right set of skills to illustrate and sell your art
  • Taking calculated risks while balancing budgets for long-term success in the creative industry
  • Shifting towards an integrated approach that combines illustration and artificial intelligence.
30 Nov 2023Ep. 18 Joe Chernov (CMO at Pendo.io)00:48:08
In today’s episode, Joe Chernov, CMO at Pendo.io, shares his expert perspective on the ways B2B marketing has changed, the myths that marketers still cling to, and the ways he and his team are marketing “through” people—not “to” people. By cultivating his team’s strengths and infusing the Pendo brand story with strong emotion, he and his team are turning Pendo into a market winner.

Join us as we discuss:
  • How to leverage KPIs to make your customers feel above average
  • The role of biases and emotional connections in purchasing decisions.
  • Shifting focus from top-of-funnel to post-opportunity engagement.
14 Dec 2023Ep. 19 Noah Elias (Founder of Noah Fine Art)00:50:44
Setting your business up for success isn't just about the resources you have; it's also about cleverly using them to create.

In this episode, we are joined by Noah Elias, Founder of Noah Fine Art, as he unravels how he has managed to fuse cleverness, creativity, and commerce to drive business success. Supported by strategic purpose and faith, Noah shares his extensive experience in the creative industry, highlighting the importance of building a transformational rather than transactional brand experience.

Join us as we discuss:
  • Why honing structure and discipline can unlock your full potential as a creative
  • How to diversify revenue streams by selling not only what you make but what you know
  • How we should be using our energy to outshine AI through innovation instead of fearing it
04 Jan 2024Ep. 20 Kohl Crecelius (CEO and Co-Founder of Known Supply)00:46:23
Great partnerships lead to thriving brands.

In this episode, Kohl Crecelius, CEO and Co-Founder of Known Supply, explores in detail how B2B partnerships have allowed his brand to achieve stable and sustainable growth while staying true to their mission of increasing the world’s access to ethical fashion.

Join us as we discuss:
  • Why a high level of production should come along with a high level of positive and sustainable impact
  • How education can be an invaluable brand resource to connect with consumers
  • The importance of language —which goes beyond words— when creating a great brand story
18 Jan 2024Ep. 21 Kaiwei Tang (Co-Founder and CEO of Light)00:48:03
Attention is the most valuable and limited resource we have as humans, and most of it goes into the vicious circle of the attention economy.

In this episode, Kaiwei Tang, the Co-Founder and CEO of Light, breaks this vicious circle and shares how the Light Phone —and the narrative behind it— is disrupting the relationship between humans, technology and data, as well as offering unique perspectives on marketing, growth, and success.

Join us as we discuss:
  • The challenges and opportunities behind creating a product that goes against the status quo
  • How word-of-mouth marketing and partnerships have allowed Light to sustain itself and maintain constant growth
  • Why brand storytelling can reshape the technology landscape
01 Feb 2024Ep. 22 Charlie Waite (Director of Product Design at Uber)00:44:57
Every day, Uber facilitates 27 million trips worldwide. How do they provide the best experience possible?

In today’s episode, Charlie Waite, Director of Product design at Uber, delves into the challenges and rewards of designing a global product, navigating diverse user bases and global nuances, and providing the safest, most efficient experience in the market. He also underscores the relevance of balancing design, user experience, speed, and company growth.

Join us as we discuss:
  • How good product design serves as a powerful differentiator for brands
  • Uber's commitment to diversifying services for increased accessibility
  • The importance of authenticity and honesty in leadership roles
15 Feb 2024Ep. 23 Nick Levesque (Creative Director at Asana)00:35:25
In this episode, we are joined by Nick Levesque, Creative Director at Asana, who shares valuable tactics and approaches on going upmarket and migrating from an SMB image to an enterprise one. With extensive experience managing teams, Nick also emphasizes the importance of becoming a salesperson in the creative industry to effectively communicate and sell your vision and creative ideas.

Join us as we discuss:
  • Nick’s four Cs brand philosophy
  • How Distinctive Brand Assets can elevate your marketing strategy to the next level
  • Expert tips for balancing passion projects with full-time jobs
29 Feb 2024Ep. 24 Melissa Rosenthal (CMO at Insight Timer)00:44:01
Disruption isn't just a buzzword—it's the lifeline of growth and innovation in today's business landscape.

In this episode, Melissa Rosenthal, CMO at Insight Timer, shares her non-traditional approach to marketing and brand growth, which has successfully propelled her to scale and redefine companies in both the media and tech spaces. Melissa also delves into the creation of a wellness app that goes beyond meditation, emphasizing a community-driven model for holistic well-being.

Join us as we discuss:
  • The significance of cultivating a movement larger than your product
  • The shift towards prioritizing retention over brand awareness
  • The pitfalls of adhering to the growth-at-all-costs playbook
04 Apr 2024Ep. 25 Jon Miller (MarTech Entrepreneur)00:38:50
This week, we’re joined by Jon Miller, (Prev: Co-Founder/CMO of Marketo, Cofounder/CEO of  Engagio, CMO of Demandbase), who shares his hard-won insights on all things marketing and MarTech. Jon has made a dynamic and innovative career out of identifying big opportunities in MarTech and has built some of the most iconic brands in the space. We talked at length about how B2B marketing and sales have changed and continue to evolve and how teams need to operate to win in today’s market, including leveraging the power of community, positioning, brand, and AI.

Join us as we discuss:
  • Effective strategies for entering market categories filled with established players
  • How companies can position themselves as trusted authorities in their industry
  • Current challenges and opportunities for marketers 
  • And much more. 
18 Apr 2024Ep. 26 Sam Oshin (Senior Director, Brand and Marketing Design at Github)00:47:27
Most Fortune 500 companies rely on GitHub for planning, building, and collaborating on software. But how did they cultivate a brand with such a worldwide transformational impact?

In this episode, we are joined by Sam Oshin, Senior Director, Brand and Marketing Design at GitHub. He delves into GitHub's evolution from a version control tool to a dominant force in enterprise software development. Sam also explores how GitHub now harnesses AI technology to drive innovation and disruption across multiple industries, as well as the crucial role storytelling has played in this journey.

We also discuss:
  • Finding the balance between personal values, family commitments, and professional advancement.
  • The hurdles of crafting a message that resonates with both enterprise buyers and individual developers.
  • The significance of brand authenticity and ongoing innovation in connecting with technical audiences.
02 May 2024Ep. 27 Bryan Saftler of Databricks01:04:59
Sustaining success in the competitive B2B landscape is no easy task. But what strategies truly secure a company's future?

In today’s episode, we are joined by Bryan Saftler, Global Head of Marketing for Communications, Media & Entertainment at Databricks, who explores the delicate balance between brand building and data-driven marketing. He shares why this fusion is pivotal and how it shapes top-of-the-funnel brand awareness and continuous brand enhancement for long-term success.

We also discuss: 
  • The business impact of the democratization of insights across teams.
  • How to incorporate nuances in messaging for the stages of the sales funnel.
  • The evolution of social media platforms towards video content and its implications in building brands.
  • And much more! 
16 May 2024Ep. 28 Erik Martin of Midjourney00:56:54
As social and emotional beings, humans lean towards brands that foster community. So, how can you build one that deeply connects with your clients and catalyzes growth?

This week we are joined by Erik Martin, Head of Community at Midjourney, as he sheds light on the crucial role of online communities in building a brand narrative that fosters trust and integrates customer feedback into product development to create meaningful user experiences.. 

We also discuss:
  • Erik’s extensive experience in building communities from Reddit to Midjourney
  • Insights into how Midjourney operates to produce AI-generated images in a co-creative environment
  • How community stories contribute to consolidating a brand's identity
  • Why transparency and direct engagement with the community are crucial for growth and feedback
  • The importance of understanding the process of community building at the smaller, human scale
30 May 2024Ep. 29 Francisco Cornejo of StoryBook00:41:17
Exhausted parents, demanding children, and the increase in screen time have created a cocktail of anxiety for everyone in the household before going to bed.

In an effort to connect parents with their children, reduce anxiety, reinforce self-esteem, and improve sleep health, Francisco Cornejo, Co-Founder & CEO at StoryBook, joins hosts Josh Ritchie and Jason Lankow to talk about how the challenges of living overseas transformed into a promising app with over 3 million downloads since its launch. Francisco shares his unique perspective on brand growth and how he has navigated obstacles as a startup CEO.

We also discuss:
  • How identifying pain points in day-to-day situations can lead to disruptive business ideas
  • StoryBook’s insights into creating a delightful customer experience that retains users in the long term
  • Francisco’s pillars for understanding growth and the importance of a smart, dedicated, and consistent team
13 Jun 2024Ep. 30 Jason Miller of Tyk00:50:17
B2B marketing is always changing, and today we're seeing brand make a major comeback.
In this episode, we are joined by Jason Miller, Head of Brand Marketing Demand and Content at Tyk, as he takes us through his eye-opening journey from music into B2B marketing. Jason dives into his mission-driven approach to tackling tough problems, scaling up, and fine-tuning the technical side of B2B marketing. He also shares some non-traditional strategies and insights on brand identity, trust, and the unique hurdles of marketing to a tech-savvy audience.

We also discuss: 
  • The relevance of risk-taking in marketing for groundbreaking impact
  • Jason’s approach to measuring brand through metrics like direct traffic, referrals, and branded search traffic
  • How to future-proof companies by focusing on customer value rather than solely serving sales
  • The importance of balancing long-term planning with agile marketing adaptations
27 Jun 2024Ep. 31 Ian Elliott of MAAP00:45:13
Only 5% of the market is ready to buy, so how do you ensure your brand is at the top of people's minds when they purchase?

In this episode, we are joined by Ian Elliott, the CMO of MAAP, a cutting-edge cycling apparel brand that's redefining the sport with a blend of performance and aesthetics. He delves deep into MAAP's unique approach to community building, the fine balance between brand campaigns and conversion marketing, and the nuances of maintaining authenticity while scaling in a competitive market.

We also discuss:
  • The importance of building strong emotional connections through brand storytelling.
  • The structure and strategy of MAAP's marketing team to achieve significant business impact.
  • The slightly irreverent and no-nonsense spirit that differentiates MAAP in the market.
11 Jul 2024Ep. 33 Soren Iverson of Iterate00:41:28
The future of design isn’t just about function; it’s about fun. 

In this episode, we are joined by Soren Iverson, Product Designer at Iterate and creator of the innovative app Stompers. Known for his satirical product interfaces that captivate social media, Soren shares his journey of infusing humor into his work to escape the rigidity of deliverables in the design industry. He discusses the ups and downs of running his business, mastering sales and marketing, and maintaining a work-life balance while also touching on his creative process, emphasizing the importance of unique niches and technological advancements in design. 

We also discuss:
  • The commodification of design due to advancements in technology and AI
  • The challenges of setting client expectations and managing team dynamics.
  • Why finding unique positioning or specialization in the design industry is key to succeed.
04 Jul 2024Ep. 32 Bob Galmarini of Databricks00:35:58
‘A brand is a living, breathing thing. A stale brand is a dead brand’

In this episode, we are joined by Bob Galmarini, Senior Director of Brand Design at Databricks, as he shares his journey leading a multidisciplinary team of one of the fastest-growing organizations in the tech space, and discusses how his team navigates the challenges of simplifying complex messaging for a technical audience. Bob also addresses the importance of telling brand stories that resonate with the buyers, no matter the complexity of the product or service, and emphasizes the areas where B2B brands can still learn from B2C. 

We also discuss: 
  • Why integrating quantitative data with emotional storytelling is key—staying data-informed rather than data-driven
  • How AI tools are being utilized to enhance creative workflows, focusing on efficiency, templatizing, and automation.
  • The necessity of finding a balance between top-of-funnel and bottom-of-funnel (BOFU) content to enhance brand awareness and engagement.
18 Jul 2024Ep. 34 Alec Hanson of loanDepot00:44:26
How can embracing digital trends and authentic human connections redefine your marketing strategy in an AI-driven world?

This week we sit down with Alec Hanson, Chief Marketing Officer at loanDepot, as he takes us through the intricacies of mortgage marketing amidst fluctuating interest rates. Drawing on his extensive industry experience, Alec discusses effective strategies tailored for navigating high-rate environments and the importance of authenticity and storytelling in brand development. Staying on top of AI and innovative technologies to stay competitive in a rapidly evolving market is key to success. Whether you're new to mortgage marketing or a seasoned professional, Alec's practical advice and forward-thinking perspectives offer valuable guidance for driving success in this dynamic industry.

Join us as we discuss:
  • The importance of utilizing diverse digital channels such as Instagram, TikTok, and Google to effectively reach and engage with modern consumers.
  • The critical need for marketers to adopt new technologies like AI and move away from outdated methods to remain competitive.
  • The significance of building genuine human connections and maintaining transparent branding to foster trust and loyalty among consumers.
25 Jul 2024Ep. 35 Gwen Lafage of Sinch00:37:49
As brands grow, communication channels tend to expand parallelly. What is the secret behind successful comapnies that can keep up and leverage with this growth? 

To delve deeper into this question, we are joined by Gwen Lafage, VP of Marketing, Global Brand and Content at Sinch, who shares the intricate balance between a long-term vision and agile marketing, paving the way for continuous and successful brand growth.  Gwen also explains how Sinch is revolutionizing brand experiences and efficiency while underscoring the often-overlooked potential of rich communication messaging

We also discuss:
  • The importance of maintaining consistency in brand messaging while allowing autonomy.
  • Gwen’s insights into 6 C’s philosophy
  • The significance of integrating AI innovations and maintaining strong, consistent brand messaging.
01 Aug 2024Ep. 36 Celene Osiecka of [24]7.ai00:36:58
AI has been here for a long time — longer before the ChatGPT boom. And now that we’ve all seen it, it’s not going anywhere.

In this episode, we are joined by Celene Osiecka, Senior Director of Conversation Design and Conversational AI at [24]7.ai, as she shares how her team focuses on enhancing customer experience, reducing risk, and navigating the challenges of the tech industry through a systemic use of conversational AI.

We also discuss: 
  • The delicate balance between data-driven approaches and the subjective, artistic aspects of conversation design.
  • How AI is transforming quality assurance, helping companies streamline training and reduce costs.
  • The roles and collaboration involved in designing effective AI-driven conversations.
08 Aug 2024Ep. 37 Josie Jeffries of Webflow00:44:57
Clarity is the cornerstone of brand success.

Understanding what your brand is to the core, and what it offers, enables you to craft a clear narrative and effectively market it.

In this episode, we are joined by Josie Jeffries, Sr. Director, Creative and Content at Webflow. Josie is a seasoned professional with an impressive career at leading teams in tech brands like X (formerly Twitter) and Slack, where she excelled in building brand awareness. She shares her insights on the importance of clarity and communication in marketing challenger brands and reveals strategies for managing change and persuading customers to switch to new platforms amidst fierce competition.

We also discuss:
  • How to appeal to both the emotional and technical needs of stakeholders.
  • The importance of balancing ambitious brand campaigns with conversion-oriented content.
  • Strategies for prioritizing creative decisions based on their return on investment.
15 Aug 2024Ep. 38 Aaron Zide of Halcyon00:37:54
How does a cybersecurity startup blend retrofuturistic vibes with innovative anti-ransomware strategies to stand out in a crowded market?

Our guest today, Aaron Zide, Creative Director at Halcyon holds the answer to this question. 

In this episode, Aaron shares invaluable insights on the challenges and opportunities of maintaining a distinctive brand identity while remaining agile and creative. He explores how Halcyon projects a retrofuturistic and serene vibe and discusses the innovative marketing strategies that have helped the brand cut through the noise and retain customers' attention in the long run.

We also discuss:
  • How to manage a global team while maintaining a unified brand tone and message.
  • The need for open-minded adaptation and embracing new marketing channels.
  • How to stay true to the brand’s unique identity while incorporating feedback and societal changes.
22 Aug 2024Ep. 39 Ryan Romero of Hoag Health System00:38:23
Healthcare has always been perceived as a very unauthentic sector in terms of brand and product. What are folks doing out there to change the landscape? 

In this episode we are joined by Ryan Romero, Creative Director, Marketing & Product Design at Hoag Health System where he is trying to radically change how users interact with healthcare providers through innovative digital health products, to save lives and improve care. Ryan shares insightful stories about elevating Hoag's brand through authentic storytelling, innovative maternity campaigns, and the development of groundbreaking applications. 

We also discuss:
  • Building design teams and a culture of innovation in a hospital setting with no prior design philosophy.
  • Strategies to attract a younger audience through compelling narratives and creative marketing.
  • Ryan’s philosophy on clear, usefulness and elegance, balancing emotive and factual elements
  • The move towards creating a unified design system for Hoag, integrating motion and building meaningful user experiences.
29 Aug 2024Ep. 40 Joe Lazer of A.Team00:37:25
Great innovations come from great teams working together, doing more than they could individually. 

And, to achieve this, companies first need to understand the problem they are trying to solve.

In this episode, we are joined by Joe Lazer, the fractional Head of Marketing at A.Team, a company revolutionizing how organizations build teams by leveraging AI. Joe shares insights into the tools developed at A.Team (Team Formation AI), the importance of brand storytelling in B2B marketing, and the emerging trend of internal evangelists as key drivers of brand and performance.

Listeners will learn:
  • The critical role of brand storytelling in building meaningful connections with audiences, even in the face of increasing AI-driven content production.
  • Why cultivating strong internal voices within a company can deliver outsized impacts on both brand recognition and sales.
  • The future of B2B marketing, with a shift toward more personalized, creator-led engagement strategies.
Check out Joe’s book The Storytelling Edge: How to Transform Your Business, Stop Screaming into the Void, and Make People Love You, his newsletter on LinkedIn, and make sure to follow him for more B2B content. 
05 Sep 2024Ep. 41 Dorian Stewart of Federato00:30:14
Branding isn’t about your appearance to your audience — it’s about the experience you cultivate for your audience.

This week, we’re joined by Dorian Stewart, Director of Demand Generation at Federato, to discuss his philosophy on fusing empathy for the end user with smart data to create impactful content that not only communicates, but resonates.

We also discuss:
  • How to balance maintaining a unified brand with the constant need for speed and experimentation.
  • Emerging trends in influencer marketing and in-person experiences in the B2B space.
  • Why focusing on customer stories and solutions is often more effective than discussing product features.
12 Sep 2024Ep. 42 Gretchen Leslie of I Will Teach You To Be Rich00:48:08
What does being rich mean to you? Is it just hitting a number? 

In this episode we are joined by Gretchen Leslie, President at I Will Teach You To Be Rich, as she shares how she and her team are empowering people to become rich, whatever that means to each individual. Gretchen talks about her hands-on approach to brand storytelling, the challenges of SEO in a volatile market, and the evolution from meticulous content creation to streamlined success.

We also discuss: 
  • How overcoming apathy by promoting confidence and joy instead of guilt and shame can lead to more successful brands.
  • The importance of finding a balance between financial management and personal fulfillment to become truly rich.
  • How developing brand and style guides enhances efficiency in content production.
19 Sep 2024Ep. 43 Christopher Clarke of Intuit00:57:03
Is your brand talking at people, or with them?

In this episode, we dive deep into the mind of Christopher “Toph” Clarke, Executive Creative Director at Intuit, the brand behind TurboTax. From his journey in creative leadership to teaching the next generation of advertising talent at ONE School, Toph shares insights into how brands can stay relevant by connecting with real people.
We will explore how personal stories, cultural immersion, and the power of authenticity can transform a business—and a career.

Listeners will learn:
  • How brands can go beyond traditional advertising by embedding themselves in local communities.
  • Why teaching not only empowers others but also sharpens your own skills as a leader and creative professional.
  • The impact of leveraging personal narratives in creating emotional connections with audiences.
26 Sep 2024Ep. 44 Radu Ranga of C100:50:50
The differentiation of the brand and the owning of the brand comes by making sure everything is aligned.

In this episode, we are joined by Radu Ranga, Senior Director, Brand Creative at C1. He discusses how his creative journey—from agency life to his pivotal role in branding for UFC and C1—has shaped his approach to branding and marketing. Radu shares insights on how to align visual identity with core messaging, the importance of understanding the emotional and rational sides of brand decisions, and the risks that paid off in his career.

Listeners will learn: 
  • How to align brand messaging across product, marketing, and sales teams
  • Effective risk-taking in creative projects and how to mitigate failure
  • Practical tips for bridging the gap between design and strategy in branding
03 Oct 2024Ep. 45 Alan Roll of Airtable00:41:30
The world of content is constantly changing, and only the best marketers can adapt to these evolving trends. 

In today’s episode, we’re joined by Alan Roll, Head of Brand Creative at Airtable. Alan’s journey from crafting narratives to leading innovation at Airtable is nothing short of inspiring. In a fast-paced market, he drives brand strategy through experiential content while leading a small but fiercely creative team. Alan reveals how Airtable has evolved in customer perception, gained a competitive edge in collaboration and operations, and shares real-world examples of its impact—along with how customer feedback continually shapes their messaging.We also discuss:
  • How a lean, multifunctional team structure can drive collaboration and deliver impactful content 
  • The AI benefits for productivity and accuracy, but the value of human creativity is irreplaceable
  • How shifting to a holistic brand approach can create a cohesive brand experience
10 Oct 2024Ep. 46 Travis Keith of JP Morgan00:35:58
“Sales enablement is the bridge between marketing and closing deals."

For this episode of Best Story Wins, we’re joined by  Travis Keith, VP of Strategic Client Content at JP Morgan, to explore the essential balance between sales and marketing integration. Travis shares a fresh perspective on uniting sales and marketing through authentic, help-first strategies. 

Tune in to hear Travis’ insights on the evolving role of social media in shaping purchasing decisions and how aligning sales and marketing can foster a more cohesive approach, driving meaningful business results.

We also breakdown:
  •  The importance of integrating marketing and sales to ensure teams have the right messaging and assets, bridging historical gaps.
  • How regular leadership meetings align campaigns and foster teamwork, driving scalable content programs.
  • Strategies for rethinking workflows and improving resource management to enhance efficiency for large sales teams.
17 Oct 2024Ep. 47 Kira Klaas of Later00:42:57
Great companies don’t just sell products—they leverage their brand to create connections that resonate. 

In this episode, we’re thrilled to welcome Kira Klaas, VP of Corporate Marketing at Later, to share her expert insights on how to make those connections truly count. Kira walks us through her strategic approach to aligning content with audience interests, the pivotal role a full-time copywriter plays in creating cohesive messaging, and how embracing diverse perspectives can help leaders overcome personal biases.

Join us as we discuss:
  • How to align your content with audience interests—authentic connections beat fleeting trends every time! 
  • Kira’s concept of Brand Market Fit
  • How to create seamless customer experiences at every touchpoint through design.
If you want to dive deeper: 
24 Oct 2024Ep. 48 Stephanie Paturzo Swingle of Instacart00:34:25
In this episode we host Stephanie Paturzo Swingle, B2B Marketing leader at Instacart

We uncover how she’s using innovative strategies—like AI-powered smart carts and dynamic co-marketing campaigns—to transform Instacart’s partnerships with CPG and retail brands, all in the name of (and informed by) the ambitious company vision of powering every grocery transaction.  We discuss the power of brand, the role of content marketing in brand-building, and what it’s like to have a multi-sided brand and marketplace like Instacart. And, we take a look into how Stephanie strikes the balance between creativity and practicality.

Join us as we discuss:
  • How Instacart nurtures a healthy and inspiring creative environment where no idea is too outlandish. 
  • What it takes to appeal to emotion in a B2B marketing capacity. 
  • The crucial role storytelling plays in driving consumer engagement and boosting sales.
  • And much more. 
31 Oct 2024Ep. 49 Chris Ollier of Bonterra00:52:01
When your customers don’t speak tech, how do you help them choose wisely—and trust you along the way?

In this episode, we welcome Chris Ollier, Senior Director of Demand Generation at Bonterra, to tackle the challenges of brand and digital strategy in the nonprofit sector.

With a wealth of experience ranging from Fortune 100 companies like Verizon and the NFL to independent projects, Chris shares his journey through diverse roles in creative design and tech startups. He discusses Bonterra's mission to drive social good through innovative software solutions for nonprofits and explores the complexities of maintaining brand authenticity amidst corporate transitions.

We also cover:
  • The significant impact of brand consistency on performance metrics like market share and brand valuation.
  • How valuable AI is in enhancing creative processes and the necessity for expert guidance and validation.
  • Bonterra's approach to brand building, focusing on straightforward design, genuine customer connections, and alignment with social good initiatives.
07 Nov 2024Ep. 50 Tamara Austring with Zapier00:40:54
Routine processes can stifle innovation and allow competitors to pull ahead. How can companies stay agile to deliver fresh, impactful work?

In this episode, we explore design operations with Tamara Austring, Senior Design Producer at Zapier's Brand Studio. As a leader in the design space, Tamara explores how adaptable, people-centered processes are the key to keeping creative teams nimble, efficient, and ready to innovate at every turn. She shares the high-stakes strategies behind continuous evaluation, the power of retrospectives, and why celebrating both wins and failures is essential for creative growth.

In this episode, we discuss:
  • Why static workflows are the enemy of innovation, and how to evolve them to stay competitive.
  • The balance between leveraging AI for efficiency and maintaining the human intuition that makes your brand unforgettable.
  • How creating a culture of trust, transparency, and challenge fuels creative teams to outperform—and what it means for the future of marketing.
14 Nov 2024Ep. 51 Elie Ayrouth of Foodbeast00:47:06
Social media is flooded with short-lived food trends and recipes, but a few brands know how to keep their edge.

In this episode, Elie Ayrouth, the brains behind Foodbeast, dishes out a spread of insights, breaking down how Foodbeast reels in over 100 million people each month. He also gives us a sneak peek into his plans for expanding into consumer packaged goods and why live events are a game-changer for building a tight-knit community.

Join us as we discuss:
  • The invaluable impact of in-person events, in building a unique, engaged community that online interactions simply can't replicate.
  • How Foodbeast maintains agility and innovation without losing focus on what already works.
  • Why authentic human storytelling is so important and how it can forge deeper connections with the audience, helping you stand out.
21 Nov 2024Ep. 52 Santi Pochat of LinkedIn00:54:08
LinkedIn has consistently proven it’s at the top of its game, no matter the economic climate. What’s the secret behind their success?

In today’s episode, Santi Pochat, LinkedIn’s VP of Brand Marketing, shares his perspective on investing in brand longevity and authentic storytelling to drive success even in tough times. Santi takes us through his journey—from Argentina’s vibrant advertising scene to leading brand initiatives at global giants like Google and Samsung. He also sheds light on how brands can thrive in a decentralized market and how LinkedIn is evolving into a dynamic hub for continuous career growth.

Join us as we discuss:
  • Investing in brand consistency during downturns drives faster recovery and stronger positioning in upturns.
  • Strong brand perception in B2B enhances client engagement, reduces churn, and improves sales efficiency.
  • Decentralizing through employee advocacy and authentic content builds genuine connections with audiences.
29 Nov 2024Ep. 53 Dan Levy from LivePerson00:38:58
Great marketing is born at the intersection of art and science, where strategy effectively meets creativity.

In this episode, we chat with Dan J. Levy, Senior Director of Product Marketing, Content, and Communications at LivePerson, to uncover the sophisticated mechanics behind brand storytelling in conversational AI.

Dan shares his expert approach to weaving compelling narratives that resonate deeply with audiences, ensuring messaging aligns seamlessly with customer values. He reveals why LinkedIn remains an unparalleled platform for fostering authentic connections in the B2B space and explains how to leverage emotional intelligence to drive decision-making in a complex market.

Join us as we discuss:
  • How ChatGPT can turn one piece of content into multiple formats, simplifying complex products into effective go-to-market strategies.
  • The power of brand storytelling: combining customer research and strategic storytelling to create a compelling, consistent narrative.
  • AI and Human Connection in B2B marketing: how leveraging AI to understand emotional drivers boosts customer engagement and fosters lasting loyalty.
05 Dec 2024Ep. 54 Adam Robinson of RB2B00:37:58
Your next big marketing move isn’t buried in your paid ads or latest campaign—it’s staring you down in the mirror.In this episode, Adam Robinson, CEO and Founder of RB2B, dives into why personal branding has become a crucial growth lever in B2B. With over 100K LinkedIn followers built around his edutainment approach, Adam shares the strategies and insights that helped him craft a compelling personal brand and grow his businesses.

We also discuss:
  • Why the future of B2B marketing is personal, humanized, and authentic.
  • How moving from full-time content creation can drastically impact your brand.
  • The importance of being the “future version” of your ideal client to create content that drives business.
  • Practical tactics for crafting engaging hooks and polarizing content that will boost your brand’s visibility and growth.
  • And much more.
12 Dec 2024Ep. 55 Lindsey Slaby of Sunday Dinner00:42:33
When everything feels urgent, it’s easy to lose focus. With leaner teams, tighter budgets, and increasing pressure to prove value, many organizations are stuck in a cycle of doing more but achieving less. Could the solution lie in doing less, but better?

In this episode, Lindsey Slaby, Founder of Sunday Dinner, shares her bold vision for modern marketing. She dives into the value of building curated communities, like her exclusive 400-member Slack group that sparks collaboration and innovation among top-tier marketers and creatives. Lindsay also explores the strategies for integrating brand and performance efforts, leveraging AI for smarter content creation, and focusing on high-impact initiatives to help organizations achieve more by focusing on less.

We also explore:
  • How annual planning can become your business’s ultimate power move.
  • Breaking down the myth of "brand vs. performance" for seamless storytelling.
  • Unlocking high-value opportunities with low and mid-funnel content optimization.
  • Why taste is the modern marketer’s secret weapon.
19 Dec 2024Ep. 56 Drue Stinnett of HubSpot00:23:55
Great content doesn’t just inform—it inspires, builds, and connects with an audience on a deeper level. In today’s episode, we’re excited to chat with Drue Stinnett, Senior Content Strategist at HubSpot! Drue walks us through her journey, from navigating the post-college job market to landing her dream role at HubSpot during some challenging times. She shares her approach to content strategy, the unique hurdles of B2B marketing, and how she strikes the perfect balance between quality and quantity in content creation.

We’ll also explore how Drue and her team are using data to take creative risks and launch innovative projects, all while proving that small, agile teams can make a huge impact in marketing.

Join us as we discuss:
  • HubSpot’s ability to use data to drive content decisions, balancing quality and quantity.
  • The guidance HubSpot offers to help users effectively implement technologies like AI.
  • How small, resourceful marketing teams can achieve big impact with innovative strategies.
02 Jan 2025Ep. 57 John Onoda of iQ 360, Inc.00:38:22
When the stakes are high, will your brand rise to the challenge—or collapse under the weight of public scrutiny?

In today’s episode of Best Story Wins, we’re going global—literally. Our guest, John Onoda of IQ 360, shares how the strongest brands aren’t just built in boardrooms but forged in the heat of crises and opportunities. With a career spanning iconic companies like Levi Strauss and General Motors, John taps into why communication, adaptability, and brand experience are more critical than ever in businesses.

We also explore IQ 360’s impactful work, from guiding Hawaii through the pandemic to supporting organizations in the aftermath of the Maui fires. Plus, John unpacks how today’s leaders can stay ahead by embracing influencer-driven narratives, workforce challenges, and the AI revolution.

Join us as we discuss:
  • How to harness the power of influencers to amplify your brand’s story.
  • Keeping your workforce inspired and aligned during turbulent times.
  • Why AI and predictive analytics are the ultimate tools for staying ahead.
09 Jan 2025Ep. 58 Kyle Lacy of Jellyfish00:39:49
The biggest mistake B2B marketers make today is prioritizing metrics over creativity. Brands that play it safe and shy away from bold risks are destined to fade into the background. 

In this episode, we are joined by Kyle Lacy, CMO of Jellyfish, as he shares actionable insights on how to pair creativity with strategic alignment to drive both brand resonance and measurable success. Kyle also explores the pitfalls of ROI-driven brainstorming and why bold bets like “Cards Against Engineering” create lasting impressions. Kyle also discusses the evolving role of B2B marketers, revealing how storytelling, good taste, and daring choices are critical to standing out in a crowded market.

We also discuss:
- Why creativity without risk is just noise—and how to take meaningful risks.
- How to balance demand generation with brand-building initiatives.
- Why traditional metrics need to be rethought to reduce stifled innovation.
- The role of storytelling in winning hearts, minds, and market share.
16 Jan 2025Ep. 59 Nate Skinner of Squarespace00:38:38
The more you post, the less your audience cares. With brands trapped in an endless cycle of content production, is the key to standing out doing less?

In this episode, Nate Skinner, Head of Brand Creative Strategy at Squarespace, shares his insights on breaking free from the "always-on" trap. He explores how Squarespace integrates bold creativity with meaningful storytelling, why personal branding is changing the B2B industry, and how AI and curated design are paving the way for successful marketing. 

We also explore:
  • The shift from quantity to quality in brand storytelling.
  • Why Super Bowl ads are still the ultimate creative risk—and reward.
  • How Squarespace is redefining social media strategy with creativity and focus.
  • The role of AI in crafting high-impact campaigns.
  • How personal branding intersects with corporate identity to drive trust.
23 Jan 2025Ep. 60 Andrew Gori of Autodesk00:37:48
It’s smart, it’s fun, and it might just change how you think about content. In today’s noisy digital world, Autodesk knows how to stand out: by telling stories that truly matter.

In this episode, Andrew Gori takes us behind the scenes of Autodesk’s human-centric content strategy, showing how his team connects with audiences in the construction industry. From his journey as an aspiring journalist to leading bold content strategies at Autodesk, Andrew shares how creativity and strategy come together to rise above the digital noise.

We also discuss: 
  • AI's impact on content discoverability, the challenges of AI-driven search results, and ongoing strategy experiments.
  • Adapting marketing strategies to become a top content destination and build a loyal audience of "1000 true fans."
  • Autodesk's upcoming global research project revealing groundbreaking insights into the construction industry.
30 Jan 2025Ep. 61 Obaid Durrani of Clay00:48:34
Your biggest competitive advantage in B2B isn't your product; it's the story that people tell themselves about your company. Today's winning brands shape the story by balancing giving people the content they want while never resting on their laurels. 

In this episode, Obaid Durrani, of Clay, shares his vision for what this means and gives examples of how he's pushing boundaries and reimagining what b2b content can and should be, which is helping to drive Clay's rapid growth and recent ascension to unicorn status. 

We also explore:
  • How to turn dry product features into captivating narratives.
  • The formula behind Clay's viral Matrix-inspired campaign.
  • What most brand leaders are still getting wrong about influencer marketing.
  • Why building "conceptual content" is the future of B2B marketing.
  • And much more. 
06 Feb 2025Ep. 62 Egan Montgomery of Backstroke00:34:54
About 85% of competing software companies are pretty much the same.

The winning companies focus on staying in the 15% that represents an opportunity to truly differentiate, which is also what the company’s goals should be tied to.

In this episode, Egan Montgomery, Co-founder and VP of Marketing at Backstroke, reveals how his generative AI-powered platform is changing how email marketing works, boosting performance by 30% compared to human-written emails. Egan also shares why “doing things that don’t scale” is the future of marketing, and how tailored in-person experiences are becoming the best way to build trust with clients. 

We also dive into:
  • Why the old B2B marketing models are crumbling and what’s replacing them.
  • How personal branding is no longer optional for founders and executives.
  • Why generative AI’s second wave will change how we work, sell, and connect.
  • Building trust in a world saturated with noise and gimmicks.
  • And much more. 
13 Feb 2025Ep. 63 Matt Hogan of HG Insights00:46:42
The biggest challenge in B2B marketing isn’t so much generating demand, but it’s keeping folks from ghosting you, even long before they enter your pipeline.

In this episode, Matt Hogan, VP of Marketing at HG Insights, reveals why B2B buying behavior has radically changed, and how most companies struggle to keep up. He breaks down the rise of shadow buying, the increasing role of CFOs and CIOs in decision-making, and why your brand is being judged before you ever get on a call. 

We also discuss: 
  • Why poor positioning is sabotaging your marketing efforts before they even begin.
  • The new golden age of cold calling.
  • Why generative AI is changing the content game—but most brands are using it wrong.
  • How to leverage data to create magnetic, high-impact marketing.
  • And much more.
20 Feb 2025Ep. 64 Michael Fitzsimmons of Mews00:35:17
It can be easy to lose sight of the need for deep emotional connections in a world where everyone seems obsessed with AI, automation, and bottom-funnel conversions. But being able to connect authentically with your customers is the lifeline of every business. 

In this episode, we sat down with Michael Fitzsimmons, VP of Growth at Mews, who shared how forward-thinking brands reject generic tactics and double down on storytelling, bold positioning, and strategic risk-taking – all with a mind to never rest on one's laurels, but rather to keep setting the bar higher and higher when it comes to quality, connection, and well, growth. He shares how AI fits into the creative process without killing originality, why content needs more taste, and how modern brands must prioritize community-building to stay relevant.

We also discuss:
  • Why most B2B brands fail at differentiation—and how to fix it.
  • The importance of owning a category instead of competing in one.
  • Why taste and human creativity are still some of marketing’s biggest competitive advantages.
  • Where AI shouldn’t be used in content marketing
  • And much more. 
27 Feb 2025Ep. 65 Ross Crooks of Column Five00:42:22
Every brand creates content, but only a few stand out. 

AI has made it easier for everyone to produce high-quality content, yet most brands get stuck in a cycle where they're creating good enough content but fail to stand out. What does it actually take to break through?

In this episode, we interviewed Ross Crooks of Column Five to explain why the past decade's content playbook is dead.

Ross shares why brands that aren't differentiated waste their time and resources, and why you should stop churning out content for content's sake and start creating with intent. 

We also explore:
  • The biggest mistake brands make when trying to stand out (and how to fix it).
  • How to inject real emotion in B2B content.
  • The importance of using AI as a tool for leverage, not a crutch.
  • How thoughtless scaling leads to generic, ineffective content.
  • And much more. 
06 Mar 2025Ep. 66 Stewart Hillhouse of storyarb00:48:23
The marketers who know how to wield AI as a force multiplier are already outpacing everyone else. Are you evolving fast enough to stay relevant?

In this episode, we sit down with Stewart Hillhouse, VP of Content at storyarb, to explore the evolving B2B marketing flywheel—where AI, creativity, and strategy must work together to keep brands growing. Stewart explains why the old approach to content marketing is dying and how today’s marketers need to think and work differently in this new AI-powered future.

We also discuss:
  • The three high-value roles marketers should be focusing on in 2025.
  • How to build AI-driven workflows without losing the human touch.
  • Why brand trust beats attribution—and what that means for demand gen.
  • The death of massive marketing teams and how to future-proof your career.
  • And much more.
13 Mar 2025Ep. 67 Jenny Thai of Vanta00:34:27
Most B2B content today feels generic: AI-generated fluff, generic SEO blog posts, and bland corporate jargon no one reads. Meanwhile, the brands that stand out—the ones people want to engage with—are playing a different game. So what’s their secret?

In this episode, we sit down with Jenny Thai, Head of Content at Vanta, to dig into how to build a winning brand through content. Drawing from her experience in crafting compelling brand narratives, leading content teams, and leveraging expert-driven content, Jenny unpacks how to create content that captures attention, resonates with people, and drives demand. 

We’re diving deep into:
  • What it takes to evolve a content strategy to move up-market.
  • Why brand awareness drives revenue.
  • What’s legit in AI-generated content, what’s overblown, and how to use it without losing your brand’s soul.
  • The rising power of expert-led content—and why if you’re not embracing it, you’re already behind.
  • And much more. 
20 Mar 2025Ep. 68 Laura Wilkinson of Vidyard00:40:03
In today’s world, attention spans are shorter than ever. 
With this in mind, marketers need to let go of outdated content tactics to embrace the future of B2B content, and some of the best ways to do this is through the smart use of video and leveraging original insights.

In our latest episode of Best Story Wins, we sat down with Laura Wilkinson, Director of Brand Marketing at Vidyard, to talk about how video is the not-so-secret weapon for cutting through the noise, and what it means to optimize for content quality over quantity. Laura shares why her team has moved away from the traditional blog, the power of AI avatars in sales, and how great storytelling is the key to building better customer relationships.

We also discuss:
  • Why video-first brands are leaving traditional content in the dust.
  • The marketing myths that need to die immediately.
  • How to make your brand unforgettable (without annoying your audience).
  • And much, much more. 
27 Mar 2025Ep. 69 Megan Brunner of Adobe00:35:58
B2B marketing doesn't need to be predictable or stale. As people’s attention span is shrinking, shouldn’t B2B content be as vibrant and creative as consumer-focused storytelling?

In this episode, Megan Brunner, B2B Content Strategist at Adobe, reveals how brands can level up their storytelling, infuse genuine creativity into their content, and move beyond traditional corporate imagery by applying the best from B2C content strategies. Megan's unique career path from action sports to working at some of the leading tech companies highlights why a willingness to be hands-on and scrappy combined with working a strategy is often the key to marketing success.

You'll learn:
  • How Adobe is setting a new standard for engaging B2B content. 
  • Why a lean, creative team can often outperform bigger, better-funded competitors.
  • Practical ways AI is quietly transforming B2B marketing.
  • And much more.
03 Apr 2025The CMO Playbook for the AI Era w/ Gabe Larsen00:42:24
If your brand only shows up when a customer has a problem, you’ve already lost the game.

In this episode, we sit down with Gabe Larsen, CMO of Kustomer, to tear into what most B2B marketers are getting wrong, and why brand isn’t a “nice to have,” function but rather the differentiator. Gabe drops the kind of no-fluff, first-principles manifesto that B2B leaders need to hear right now: customer service starts at hello, not help.

We break down:
  • Why “AI-powered” means nothing if your messaging isn't good enough.
  • How to build a prolific, persistent drumbeat that earns attention.
  • Why LinkedIn is the new B2B battleground (and most marketers are whispering).
  • How digital workers, partnerships, and sharp storytelling are redefining GTM in real-time.
10 Apr 2025How Notion Built a Cult Through Content w/ Notion’s Drew Evans00:46:11
If your content doesn’t have a ‘so what,’ you shouldn’t bother hitting publish. 

Drew Evans, who leads B2B content strategy at Notion, joins the show to talk about why storytelling—not templates, tools, or tired SEO tactics— moves the needle in B2B marketing.

Drew makes a strong case for substance over spam by emphasizing the importance of a great writing comeback. He gets candid about what’s broken in B2B and what marketers need to prioritize instead.

We also explore:
  • Why traditional blog content is dying and what’s replacing it.
  • The role of community in shaping a brand’s content strategy.
  • How to turn customer stories into compelling narratives (without sounding like a sales pitch).
  • The untapped power of Notion as a storytelling tool.
  • Why storytelling is making a comeback in B2B marketing—and why it’s the best way to stand out in an AI-driven world.
17 Apr 2025How Smart Founders Use AI to Win w/ Hiten Shah00:56:46
Today, thinking about AI completely replacing humans is impossible. Why? Because it means replacing creativity, context, and more importantly, intuition. 

Hiten Shah, serial entrepreneur, investor, and now working on AI at Dropbox, joins Josh and Jason to discuss how smart marketers and builders are using AI as a thought partner rather than a content machine. Hiten also drops hard-earned wisdom on what marketing still gets wrong, why engineers still (and will likely always) lead the startup ecosystem , and the explanation of why “the best story wins” is more than just a nice phrase.

We discuss:
  • Why getting the best from AI starts with better prompting and pre-prompting conversations. 
  • Why the road to content quality often starts with content quantity. 
  • Augmenting vs replacing human task management with AI.
  • The biggest myths about AI-generated content, and why it’s dangerous for your brand.

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