Radically Transparent

Hosted by Oktopost

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Episodes

177

Latest episode

Aug 2026

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About the show

Radically Transparent, presented by Oktopost, is a podcast geared towards the modern-day B2B marketer. Host Jennifer Gutman and her guests are a mixture of renowned marketing and sales leaders from B2B marketing organizations around the globe. Each episode shines a light on the inner workings of B2B leadership-- including what keeps successful CEOs, CMOs and VPs up at night, professionally. The conversations are real, raw and authentic all while revealing to listeners the unfiltered, not-so-known truths of today’s most interesting marketers.

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60 recent

August 10, 202627 min

How to prove the ROI of executive branding (Without the attribution headache) with Ross Simmonds

In this episode of Radically Transparent , Ross Simmonds, CEO and Founder of Distribution.ai, stops by to explore what it really takes to scale executive branding with AI while keeping every post authentic and measurable. Ross explains how marketers can use AI to increase output without sacrificing an executive's unique voice, including practical techniques like creating an "anti-AI-isms" document to maintain consistency and authenticity to safeguard brand integrity.

July 15, 202628 min

How to build a “Marketing Brain” using Claude with Anna Fisher

Are you drowning in the nonstop pressure to adopt AI while staring down an aggressive quarterly pipeline goal? You aren't alone. In this episode of Radically Transparent, Anna Fisher, CMO of Kustomer, pulls back the curtain on how she is steering her marketing, SDR, and partnership teams to integrate AI into their day-to-day workflows without losing the strategic thinking that drives revenue.Anna explains that while every B2B team is being told AI can make them faster and more efficient, widespread adoption across every industry also makes it harder to stand out. As more organizations rely on similar AI workflows and playbooks, differentiation comes from the quality of your strategy, your data, and your true understanding of the customer, not the tools themselves.

April 29, 202651 min

Employer branding that actually drives hiring results with Daniel Callaghan

What really makes top talent choose and stay at your company? Daniel Callaghan, Global Employer Brand Manager at Payoneer, breaks down the human side of employer branding and how B2B companies can turn connections into lasting engagement on this episode of Radically Transparent.Marketing leaders will find particular value in Daniel's take on employee advocacy. He explains why HR professionals and marketers must collaborate to empower employees to share their own stories, noting that personal posts often garner significantly higher engagement than polished corporate content. Whether it's discussing the "magic" of immeasurable referrals or the shift of how candidates evaluate employers in the age of AI and Glassdoor transparency, Daniel provides a masterclass in building a brand that attracts and retains top-tier talent.Hot topics:- Defining the "Employer Brand Dust": Why employer branding is just as much about internal retention and employee happiness as it is about external candidate attraction (we even talk about it in this blog).- The great ownership debate: Should employer branding sit in Marketing, HR, or the Office of the CEO? Daniel shares his vision for the future of the role.- The power of employee advocacy: How to balance human, vulnerable storytelling with corporate messaging to drive real ROI and "micro-decisions" in the minds of candidates.- Measuring the immeasurable: Practical tips for tracking the impact of employer brand through data, from career site funnels to the influence of "verified" social profiles.Love what you heard? Be sure to like and subscribe!

April 23, 202648 min

Is your brand LLM-ready? The death of the funnel with Lisa Vecchio

The traditional B2B funnel isn't just dying, it’s being rewritten by LLMs as a B2B marketing AI strategy that prioritizes brand equity and discoverability. Lisa Vecchio, Senior Director of Marketing at Veed, joins the Radically Transparent podcast to discuss why the C-suite is spiraling into 'AI anxiety' and why your SEO strategy might be obsolete by next quarter.

February 26, 202630 min

How to architect B2B influencer marketing for pipeline, not just impressions, with Justin Levy

Influencer marketing is not a brand play in B2B. It's a revenue engine. Host Jennifer Gutman⁠ sits down with B2B marketing leader and author Justin Levy⁠ to reveal how to architect influencer programs that drive pipeline, prove ROI, and secure lasting budget.

February 12, 202650 min

How leading law firms stand apart with Roy Sexton

Vedder CMO, Roy Sexton , unpacks the tension many legal leaders face: the desire to differentiate while staying within the industry’s comfort zone. He shares how a “work with the willing” mindset helps drive change from within, turning hesitation into momentum. The result is not louder marketing, but more intentional positioning that aligns culture, leadership, and brand. A thoughtful conversation for legal marketers and firm leaders ready to move from safe to standout. Looking for more insights on social media strategy for legal services? Explore how leading firms are turning social into a measurable growth channel.

January 29, 202626 min

Rebranding starts with listening (AI can help), with Michael Yehoshua

CMO of WiseStamp, Michael Yehoshua, shares why rebrands don’t fail because of bad design, but because marketers stop listening. In this episode of Radically Transparent , he explains how customer conversations became the foundation of WiseStamp’s magnificent rebrand. Michael also breaks down how AI in rebranding works best when it’s used to listen, not just create, offering a practical, customer-led approach for CMOs and brand leaders navigating rebrands or positioning shifts.

December 4, 202534 min

The truth about AI readiness in B2B marketing with Shaun Ma

Most B2B teams are racing to adopt AI but few are structurally ready for it. In this episode, Shaun Ma, VP of Digital Customer Engagement at Schneider Electric, joins Jennifer Gutman to break down the real AI readiness gap in B2B marketing. From unused data and fragmented tech stacks to unclear ownership and outdated AI habits, Shaun reveals why “plug and play” doesn’t exist in B2B and what CMOs must fix to see meaningful impact. A must-listen for leaders looking to future-proof their marketing organization.

October 28, 202519 min

How to become the AI architect of your marketing organization with Archana Dhankar

Archana Dhankar, a Global Marketing & AI Leader, a LinkedIn Top Voice, a TEDx Speaker, a Top 10 Marketing Influencer, and a B2B Social Media Rising Star, unpacks what it means to be a true AI architect in B2B marketing. For any B2B marketing leader aiming to lead with confidence in an AI-first world, Archana’s message is clear: you must become the AI architect of your organization. This episode is your blueprint for getting started.

September 25, 202521 min

The Human-AI partnership: Why consistency is the future of customer experience with Tori Jeffcoat

Gainsight’s Director of Product Marketing, Tori Jeffcoat, unpacks the future of customer experience. Discover why delivering a consistent, unified experience across every touchpoint is the ultimate goal, and how AI can be a powerful partner in achieving it.