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Best Story Wins

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

PublishesWeeklyEpisodes136Founded3 years ago
Number of ListenersCategories
MarketingEntrepreneurshipBusiness

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Artwork for Best Story Wins

Latest Episodes

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

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

Twilio used to read like a company built for developers and nobody else. Then it found one word that made every audience feel like they belonged to the same tribe.Adam Morgan, VP of Brand and Creative at Twilio, spent three months finding that word "... more

YouTube

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Recent Guests

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
Dan Reid
Creative Director at Optimizely
Optimizely
Episode: The Irreducible Part: Taste, Judgment, and the Stories Machines Can't Tell — with Julianne DeVincenzo & Dan Reid from Optimizely
Mathew Barnes
Brand leader with IBM HashiCorp background, expert in brand systems and storytelling
IBM, HashiCorp
Episode: Clarity Wins: Why Taste Can't Be Prompted with Mathew Barnes of IBM
Hadassah Pegado Dalisay
Lead content strategy, SEO, and AEO at Outreach
Outreach
Episode: The Death of the Keyword — And What Comes Next with Hadassah Pegado Dalisay of Outreach

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
  • 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.

Apple Podcasts
#174
Russia/Business/Marketing

Talking Points

Recent interactions between the hosts and their guests.

The Irreducible Part: Taste, Judgment, and the Stories Machines Can't Tell — with Julianne DeVincenzo & Dan Reid from Optimizely
Q: What future vision do you have for Optimizely's brand story a year from now?
A year from now, we want clearer brand recall and a distributed narrative that shows how AI works in marketing, with world-class studio collaborations and cinematic storytelling that demonstrates real customer impact and outcomes rather than just product features.
Why Nobody Trusts a Brand They Just Met with Amit Singh
Q: What's your take on AI's role in brand measurement and insights?
AI can dramatically accelerate data collection, trend spotting, and visualization, but human interpretation is essential to translate insights into decisions that align with brand goals.
Why Nobody Trusts a Brand They Just Met with Amit Singh
Q: How do you think about sustaining human-centered storytelling at scale?
The core is to keep the human experience at the center, ensure emotions drive decisions, and use AI to handle scalable tasks while humans guide strategy, empathy, and nuanced storytelling.
The Death of the Keyword — And What Comes Next with Hadassah Pegado Dalisay of Outreach
Q: Can you share how you're using transcripts and proprietary data to drive content strategy and what the future of this approach looks like?
We analyze sales calls, webinars, and community discussions to extract patterns; this informs a signal-driven content strategy, leveraging proprietary data to differentiate and connect content to actual buyer language and needs, with ongoing content retros and quarterly refreshes.
The Death of the Keyword — And What Comes Next with Hadassah Pegado Dalisay of Outreach
Q: How are you approaching the shift to AI search and helping others at Outreach who may not have an SEO background?
We focus on visibility, authority, and execution—building interconnected content ecosystems, using AI to surface buyer questions and operational signals, and tying content to revenue outcomes rather than just keywords.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

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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Which podcasts are similar to Best Story Wins?

These podcasts share a similar audience with Best Story Wins:

1. Design Better
2. The Prof G Pod with Scott Galloway
3. Pivot
4. The Indicator from Planet Money
5. Hard Fork

How many episodes of Best Story Wins are there?

Best Story Wins launched 3 years ago and published 136 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. Sonja Jacob Silveira
2. Adam Morgan
3. Matt Scribner
4. Bill Kenney
5. Amit Singh
6. Julianne DeVincenzo
7. Dan Reid
8. Mathew Barnes

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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