After helping scale three of the fastest-growing SaaS companies in history — Slack, Zendesk, and Salesforce — Bill Macaitis joins Brand Humanity Show host Anthony Kennada for a candid, data-backed conversation about the tension every B2B leader feels: brand vs. demand in the age of AI.

At a time when the traditional marketing playbook is being rewritten in real time, Bill brings both pattern recognition and proof. Together, they unpack why brand isn’t a “nice to have” — it’s the compounding asset that makes demand more efficient, more durable, and more human.

This isn’t theory. It’s a masterclass from someone who has built iconic categories from the inside.

They explore how marketing leaders can defend brand investment in boardrooms obsessed with pipeline, how to balance short-term performance with long-term equity, and why emotional connection may be the last true moat in a world of infinite AI-generated noise.

Topics we cover:
– What scaling Slack, Zendesk, and Salesforce taught Bill about brand as a growth lever
– The false binary of brand vs. demand (and how to reframe it with data)
– Why CFOs cut brand first — and how great CMOs win that conversation
– The metrics that actually prove brand impact in B2B
– Category creation, distinctiveness, and standing out in saturated markets
– How AI increases the premium on authenticity and human connection
– Why the future of B2B marketing looks more like consumer than we think

If you’re a founder, CMO, or growth leader trying to navigate efficiency pressure without sacrificing long-term brand equity, this episode is both a strategic playbook and a mindset shift.

Because in a world where everyone has access to the same tools, brand humanity might be the only advantage that compounds.

Marketing isn’t just changing — it’s collapsing into product.

Anthony Kennada sits down with Paul Adams, Chief Product Officer and Interim CMO at Intercom, to unpack what it actually means to build, market, and lead in an AI-native world. Drawing from Intercom’s bold decision to bet the company on Fin — its AI support agent — Paul shares a rare, inside look at how founder conviction, product obsession, and radically human marketing converged to fuel one of the most consequential pivots in SaaS history  .

Together, they explore why the old SaaS playbook broke, why marketing calendars had to be deleted, and why the future belongs to full-stack marketers who understand AI as deeply as they understand people. From anthropomorphizing agents to rethinking launches, speed, education, and even how hard we should work, this conversation challenges nearly every assumption about modern marketing leadership.

Topics we cover:

– Why AI is collapsing the boundary between product and marketing

– How Intercom bet the company — and culture — on Fin

– The shift from polished marketing to radically human communication

– What “full-stack marketing” looks like in an AI-native company

– Why education is becoming marketing’s most important job

– Launching without Hollywood demos — and why authenticity wins

– Founder mode, speed, and knowing when to burn the calendar

– Why tired leaders make bad decisions (and how creativity actually emerges)

If you’re a CMO, founder, or product-led leader navigating the AI transition, this episode offers a clear signal through the noise — and a reminder that in the intelligence era, the most durable advantage is still deeply human.

After 13 years building Gainsight and pioneering the Customer Success movement, Nick Mehta sits down with Anthony Kennada and Scott Salkin for his first in-depth conversation since stepping down as CEO — and it’s a masterclass in what it means to lead with humanity in a world being rewritten by AI.

They explore the full arc of Nick’s journey — from defining “human-first” leadership and shaping company culture around vulnerability, to learning how to let go, face adversity, and rediscover identity on the other side of success. Nick opens up about what transition really feels like, the myth of linear progress, and how creativity, writing, and humor became anchors through uncertainty.

Together, they examine how AI is challenging every founder and CMO to think from first principles again — to replace the old playbooks with curiosity, humility, and a renewed sense of purpose. They also unpack why Brand Humanity may be the ultimate moat when everything else looks the same.

Topics we cover:

– The untold story behind coining “Human-First”

– What it takes to step away after building a company for 13 years

– Vulnerability as a leadership superpower (and how not to fake it)

– Why “I don’t know” is the new mark of confidence

– How AI is redefining what founders and CMOs need to unlearn

– Creativity, poetry, and humor as outlets for grounded leadership

– The intersection of brand, culture, and authentic connection

– Why humanity might be the ultimate differentiator in business

If you’ve ever wondered how to lead with heart through seasons of uncertainty — or how to stay human in the age of AI — this conversation with Nick Mehta is a rare and deeply honest guide for the journey ahead.

The playbook for modern marketing is being rewritten in real time. Anthony Kennada sits down with Jake Saper, General Partner at Emergence Capital — one of the earliest backers of category-defining companies like Salesforce, Zoom, and Gusto — to explore how AI, market velocity, and boardroom expectations are transforming what it means to be a CMO today.

Jake shares a front-row view of the AI-native startup era, where growth happens faster than ever, capital markets are “bananas,” and differentiation in a sea of sameness has never been harder — or more essential. Together, they unpack why creativity and humor matter in serious industries, why first-principles thinking is beating experience in the boardroom, and how great marketing leaders are re-potting themselves to thrive in a wickedly fast-moving era.

They also dig deep into ICP discipline, channel experimentation, and the surprising power of referrals over events in modern growth strategy — plus, yes, B2B musical theater.

Topics we cover:

– Why creativity and humor build human connection in tech

– How the CMO role is evolving in the AI-native era

– Why boards are favoring slope over experience

– Reinvention case study: Intercom and Finn

– The “bananas” early-stage funding environment

– ICP discipline as a marketing superpower

– Referrals vs. events: what the data actually says

– How great leaders re-pot themselves to thrive in change

If you’re a CMO, founder, or marketing leader staring down a new era, this conversation will give you both a playbook — and permission — to build differently.

The CMO role is in the middle of an identity crisis — and a rebirth. AI-first founders are prioritizing distribution, growth, and taste over playbooks of the past. Experience still matters, but today, aptitude, storytelling, and the ability to resonate with first-time founders matter more.

Anthony Kennada sits down with Cameron O’Brien and Amber Weinberg, co-founders of Aperture Partners (a boutique GTM executive search firm behind placements at Elastic, Fivetran, Anthropic, Fal.ai, Synthesia, Retool, and more), to unpack how the marketing leadership search is being rewritten in real time.

They explore how the expectations of CEOs have shifted, why “marketing needs a rebrand,” and what both candidates and companies must do to win in this new era of work.

Topics we cover:

– Why aptitude is outpacing experience in CMO hiring

– How to communicate marketing’s value to first-time founders

– The rebrand marketing desperately needs

– What top candidates are really looking for right now

– How human-first leadership can be a strategic advantage

– Practical advice for CMOs navigating career transitions in the Intelligence Age

If you’re a CMO, founder, or GTM leader navigating the AI era, this conversation will help you see — and seize — the opportunity in the shift.

In a world where AI can write, design, and analyze in seconds, one thing remains uniquely human: story. Anthony Kennada sits down with Nancy Duarte — CEO of Duarte, Inc., best-selling author, and the force behind some of the world’s most iconic presentations — to explore why storytelling has never been more essential for brands, leaders, and movements.

Nancy shares timeless insights from decades of helping leaders at Apple, TED, and beyond communicate ideas that move people. Together, they unpack why empathy is the heart of great storytelling, how tension (“what is” vs. “what could be”) transforms messages into movements, and why data alone can’t persuade without emotion.

They also explore the evolving dance between humans and AI in storytelling — and why the future belongs to those who can combine clarity, craft, and connection.

Topics we cover:

– Why storytelling is the most human act in business

– How to use tension and rhythm to move audiences

– The relationship between data and emotion in persuasion

– How to make ideas stick — and get them funded

– Storytelling as a language to build culture inside and outside your company

– What legacy really means in leadership

If you’re a CMO, founder, or leader navigating the AI era, this conversation will remind you why story is still the most powerful tool in your brand’s arsenal.

mbition has always been a badge of honor in business — but in today’s AI-driven world, the way we pursue it may be breaking us. Anthony Kennada sits down with Amanda Goetz (CMO, founder of House of Wise, and author of the forthcoming Toxic Grit) to explore why modern ambition needs a reset.

They unpack how grit can turn toxic when it ignores the seasons of life, why hustle isn’t always the enemy, and how intentionally stepping into the different “characters” we play — founder, parent, partner, creator — can restore balance and humanity to our work. Amanda also shares lessons from building community-led brands, navigating portfolio careers, and why leaders’ personal health directly shapes the companies they build.

Topics we cover:

– What “toxic grit” really means — and how to avoid it

– Why work-life balance is a myth (and what to do instead)

– How to embrace ambition without burning out

– The role of humanity in how leaders show up and build brands

– Why portfolio careers may define the future of work

– Practical ways to love what you have while pursuing what’s next

If you’re a CMO, founder, or ambitious professional rethinking how to thrive in the Intelligence Age, this episode will challenge you to redefine ambition on your own terms.

Pre-order Amanda's book Toxic Grit: How to have it all and (actually) love what you have right here: https://www.amazon.com/Toxic-Grit-have-actually-love/dp/146423325X?sr=8-1 

In a world where AI models are shaping what the market knows—and doesn’t know—about your company, public relations is no longer optional. It’s existential.

Anthony Kennada sits down with Emilie Gerber, founder of Six Eastern and longtime comms leader for startups and venture firms, to explore how PR has shifted from a “nice-to-have” to a core survival strategy for B2B brands.

They unpack why credibility and third-party validation are now mission critical, how earned and owned media actually complement (not compete with) one another, and what it takes to build brand trust in an AI-driven world.

Topics we cover:

– Why AI has revived the importance of third-party media citations

– The limits of trying to “game” LLMs with PR coverage

– How owned media and PR should work hand-in-hand

– Practical ways CMOs and founders can build credibility with reporters, podcasts, and niche outlets

– Why authenticity and humanity—not hype—are what resonate most with media

If you’re a founder, CMO, or marketing leader trying to understand how to stay visible and credible in the Intelligence Age, this episode will help you reframe PR as a foundational piece of your go-to-market strategy.

Speed and efficiency have become the default values in business — but in the process, marketing is losing its creativity, humanity, and soul. Anthony Kennada sits down with Robert Rose (best-selling author of Valuable Friction and co-founder of the Content Marketing Institute) to explore why slowing down might actually be the most radical strategy in today’s AI-driven world.

They unpack the dangers of treating marketing as a machine, the role of authenticity in an era of “feature-function” startups, and how leaders can introduce valuable friction into their work to build brands that last.

Topics we cover:

– Why “real beats perfect” in content and campaigns

– How AI can help (or hurt) creativity and brand trust

– The difference between building for the moment vs. building for the brand

– Why owned media must be treated like a product, not a tactic

– Practical ways to reintroduce friction that sparks creativity

If you’re a CMO, founder, or marketing leader feeling trapped in the Cult of Speed, this episode will challenge you to rethink how you create, lead, and build brands with lasting value.

Executives today can’t afford to hide behind their company logo. Customers want to buy from people — leaders with a point of view, a vision of the future, and the courage to show up authentically. Anthony Kennada sits down with Melissa Rosenthal (Co-founder & CEO of Outlever, former BuzzFeed, Cheddar, and ClickUp exec) to unpack the shifting role of executives on LinkedIn and beyond. They explore why visibility matters, how to balance authenticity with professionalism, and what it takes to own your brand narrative in the AI era.

Topics we cover:

– The difference between being a “creator” and an executive with a voice

– Why authenticity (without oversharing) is the new currency of trust

– How to fight — or work with — the algorithm without losing your humanity

– The evolving relationship between rented channels (like LinkedIn) and owned media

– Practical ways to prepare leaders to succeed as spokespeople on social

If you’re an executive, founder, or marketing leader wondering how to stand out online without falling into the trap of “creator culture,” this episode will give you the playbook.