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Best Story Wins

Column Five
B2B Marketing
Branding
Marketing
Content Marketing
Customer Experience
Brand Building
Storytelling
Artificial Intelligence
AI In Marketing
Community Building
SEO
Brand Storytelling
Digital Marketing
Marketing Strategy
Brand Marketing
Design
Customer Service
Brand Awareness
Content Creation
Linkedin

Welcome to “Best Story Wins,” a podcast for marketing and branding professionals looking to unlock their growth potential. Hosted by Column Five—a B2B marketing agency that specializes in brand and content marketing for SaaS companies—each episode features insightful conversations with industry leaders who are winning customers’ hearts and minds by building world-class brands. Tune in to hear expe... more

PublishesWeeklyEpisodes137Founded3 years ago
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MarketingBusinessEntrepreneurship

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Artwork for Best Story Wins

Latest Episodes

Everyone with a prompt window now calls themselves a creative, and the feed shows it: the same look, the same motion, the same instantly forgettable output on repeat. The teams still cutting through aren't generating more than everyone else. They're ... more

YouTube

Everyone on your team can suddenly make content. That's not the win it sounds like, it's how a brand starts dissolving, one "good enough" post at a time.

Ross Crooks, co-founder of Column Five, has a fix that flips the whole production model: stop tr... more

YouTube

Every designer you know is quietly panicking about the same thing: their Figma hours dropped from 90% of the week to 30%, and nobody told them what to do with the other 60%. Is that a crisis or a promotion?

Maria Irie runs brand at Chili Piper with ... more

YouTube

Every AI tool you use was built to keep you happy, not to make you right. That's a problem when "happy" is also the fastest route to content nobody remembers.Sonja Silveira has run content teams at Meta, athenahealth, and now Cisco, and she's done wi... more

YouTube

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Recent Guests

Nicholas Sickleton
Creative director and designer
Huntington Beach, California
Episode: Taste beats Trends with Nick Sickleton
Ross Crooks
Co-founder, Column Five
Column Five
Episode: Why Content Systems are the Future with Ross Crooks of Column Five
Maria Irie
Head of Brand Design at Chili Piper
Chili Piper
Episode: The Small Team Advantage: Turning Size into a Superpower, with Maria Irie of Chili Piper
Sonja Jacob Silveira
Lead Thought Leadership and Editorial Content Strategy at Cisco
Cisco
Episode: Beige Is What Happens When Nobody's Brave Enough to Be Wrong with Sonja Silveira of Cisco
Adam Morgan
VP of brand and creative of Twilio
Twilio
Episode: AI Made Brand the Only Thing Left That Matters with Adam Morgan of Twilio
Matt Scribner
Growth Designer at Atlassian
Atlassian
Episode: Taste Is the Only Thing AI Can't Generate (Yet) with Matt Scribner of Atlassian
Bill Kenney
Co-founder and CEO of Focus Lab
Focus Lab
Episode: Stop Measuring Brand Like a Performance Channel with Bill Kenney from Focus Lab
Amit Singh
Brand marketer with experience at Adobe, American Express, Starbucks, Nintendo
Independent/Consultant (formerly Adobe, American Express, Starbucks, Nintendo)
Episode: Why Nobody Trusts a Brand They Just Met with Amit Singh
Julianne DeVincenzo
Head of Content Strategy at Optimizely
Optimizely
Episode: The Irreducible Part: Taste, Judgment, and the Stories Machines Can't Tell — with Julianne DeVincenzo & Dan Reid from Optimizely

Hosts

Josh
Host of Best Story Wins, co-hosts show, leads introductory and exploratory questions
Ross
Co-host, provides brand, product, and storytelling expertise in discussions

Reviews

5.0 out of 5 stars from 27 ratings
  • Best story winning

    Chock full of insights from guests across a wide variety of industries, disciplines, perspectives. Good for lovers of both personal career reflections and tactical takeaways to practice.

    Apple Podcasts
    5
    Media_HW
    South Africaa month ago
  • Great for B2B marketers

    If you’re a B2B marketer, it’s a great podcast to hear perspectives from pros across different industries. (I also appreciate that it’s not 1.5 hours long.) Good info so you can get in and get on with your day.

    Apple Podcasts
    5
    Katy from the Coven
    United States3 years ago
  • Great Guests and Super Imformative

    I really like the collection of guests on this show. Most are CMOs or VPs at well respected tech companies, and it’s really cool to get a peek behind the curtain. Keep it up!

    Apple Podcasts
    5
    Family Band
    United States3 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Lengthy, deeply practical without being overly long; high value for sponsorship and guest pitching.
Listeners appreciate diverse perspectives from CMOs and VPs across tech, offering practical, actionable insights.
Guests are often senior marketers or agency leaders, providing behind-the-scenes looks at brand governance and strategy.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Why Content Systems are the Future with Ross Crooks of Column Five
Q: How do you balance automation with human judgment in brand work?
Use AI to handle production and repetitive tasks, but preserve human judgment for taste and key brand decisions, feeding feedback into the system to continuously improve the brand encoding.
Why Content Systems are the Future with Ross Crooks of Column Five
Q: How is a content engine different from a content system?
A content system is the full end-to-end workflow, while a content engine is the production component for a specific format or channel, with defined inputs, processes, and checks.
Why Content Systems are the Future with Ross Crooks of Column Five
Q: What is a brand content system and why do we need it now?
A brand content system encodes brand decisions at the input stage, using a machine-readable foundation that guides production and allows AI tools to generate on-brand content with human review where needed, thereby increasing volume and maintaining taste.
The Small Team Advantage: Turning Size into a Superpower, with Maria Irie of Chili Piper
Q: What role does authenticity play in your branding strategy, especially with AI on the horizon?
Authenticity and human relationships are central; the brand purpose is to maintain a distinct voice that AI cannot replicate, balancing practical automation with the need for real human connections in events and customer interactions.
The Small Team Advantage: Turning Size into a Superpower, with Maria Irie of Chili Piper
Q: How does the head of brand design operate in a small, scrappy team at Chili Piper?
She acts as the brand steward and enabler, ensuring coherence while empowering teams across the company to execute initiatives on-brand and on schedule, aided by a solid system and AI tools that reduce repetitive work.

Audience Metrics

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Frequently Asked Questions About Best Story Wins

What is Best Story Wins about and what kind of topics does it cover?

A sharp focus on B2B branding, product storytelling, and how AI reshapes enterprise marketing dominates recent episodes. Guests range from brand leaders at Cisco and Twilio to design and marketing ethics experts at Atlassian, Optimizely, and Outreach, with recurring themes around brand governance, human-centered storytelling, and building scalable brand systems in large tech organizations. Notable threads include balancing speed and quality, maintaining authentic voice amid AI-enabled workflows, and the tension between brand investment and measurable outcomes. The show frequently features practitioners who bridge brand strategy with product and design, offering practical frameworks for governance, editorial systems, and audience-focused sto... more

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1. Pivot
2. The Indicator from Planet Money
3. Pod Save America
4. The Bill Simmons Podcast
5. Up First from NPR

How many episodes of Best Story Wins are there?

Best Story Wins launched 3 years ago and published 137 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Best Story Wins?

Recent guests on Best Story Wins include:

1. Nicholas Sickleton
2. Ross Crooks
3. Maria Irie
4. Sonja Jacob Silveira
5. Adam Morgan
6. Matt Scribner
7. Bill Kenney
8. Amit Singh

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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