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The SaaS Brand Strategy Show
The SaaS Brand Strategy Show
Author: DRMG
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As marketing team and agency leaders specializing in B2B and B2C category creation, your co-hosts Dustin Robertson, and Mike Geraci talk all things SaaS. We dive deep into in our software experience with brand and business strategy, fundraising with the right story, strategic narratives, the voice of the customer, and anything in service of SaaS business leaders owning the brand that drives demand.
52 Episodes
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In this episode of the SaaS Brand Strategy Show, DRMG welcomes Winston Binch, Chief Brand & Experience Officer at Gale, for a frank conversation about the shifting ground under marketers’ feet.We unpack:Why Cannes has shifted from a creative director’s festival to a CMO showcaseWhat 70% of CFOs get wrong about AI’s role in marketingHow big agencies are reengineering workflows around AI—from back office to big ideasThe real opportunity in the Creator economyHow strategy, not software, unlocks both efficiency and boundary-pushing creativeIf you’re asking “How are we using AI to drive brand innovation, not just automation?”—this one’s for you.
Too many SaaS companies are leaning on “modern” as their go-to positioning—modern data stack, modern payroll, modern analytics. In this episode, we break down why “modern” isn’t a meaningful differentiator, how it fails to connect with what customers actually care about, and what to use instead to build a defensible, outcome-driven brand narrative.
When an early stage company pursues a new category design strategy, leadership in the Sales, Product, Marketing, CS, and Development departments response can be summed up as, "Great, now what?" Now What is the gap jump between strategy and tactics, between idea and action, and it can feel massive and intimidating.
In this episode of The SaaS Brand Strategy Show, we talk to Bridget Quinlan, the Chief Revenue Officer of PFL.com. In the year since DRMG worked with PFL on their category design strategy, Bridget and her team have done a masterful job of bringing the new Hybrid Experience (HX) category to market, aligning and activating the entire organization around the strategy. It is a case study on the time, temperament, and resources required to go from idea to action.
Bridget discusses her experience in leading category design strategies, including:
The timeline and order of activations across the company around a category design strategy
How to build momentum and consensus across the organization.
Why it is important to show incremental value as you go.
The importance of agility and a collaborative innovation process
How to get core messaging infused in the brand and product
And much more.
Bridget's answer to "Now What?" is to take it step-by-step, prioritizing initiatives in terms of impact and priority, and not assuming there is a master plan work plan that will make sense to everyone. It's a great take on a tricky execution.
Thanks to Bridget and PFL for the insights.
Finance people are notoriously skeptical when it comes to anything associated with the word brand. In their world view, something as esoteric as brand had better be supported with concrete KPIs to back up the investment.
As veterans of Palantir's FP&A department with a big idea for a new SaaS product, the Mosaic team were convinced that they had solid product market fit, but they were also acutely and painfully aware that they lacked a compelling way to tell and sell their story to investors and the market.
On this episode of The SaaS Brand Strategy Show, we sit down with Mosaic co-founder Joe Garafalo to discuss the company’s road to their Series B round, which they just announced.
This is an audio case study on how a start-up can go from 0 to $46 million in just over 12 months through clarity and commitment, to an idea and a strategy.
Their story is a confirmation in the power of brand strategy, even/especially for finance people. Except now they refer to themselves as Strategic Finance people.
Congrats to Joe, Bij, Brian and the entire Mosaic team. Proud and psyched to be part of the success.
- DRMG
This episode’s a cross-post from Content Blocks, hosted by Joe—who we first met while he was leading content at Mosaic, one of our early DRMG clients. We worked with their team on the Strategic Finance category strategy, and in this conversation, Joe talks about how that work gave him a real foundation to build content that actually resonated with the market.We also dig into how category strategy differs from traditional positioning, what it means to “make the news,” and why a good story is the most strategic move you can make.
Last week, Dustin traveled to Texas for a round-table discussion at a publicly-traded real estate development firm's retreat. The panel's topic was (TBD). What Dustin discovered was that the very same dynamics that push SaaS startups to seek greater clarity and alignment on their positioning exist in a large real estate bureaucracy: How do we establish competitive differentiation in the market, and, how do we go to market with that strategy?This week, Dustin and Mike unpack the similarities and discuss the approaches required to solve the conundrum, regardless of size and market.
This episode of the SaaS Brand Strategy Show goes back in time for timeless truths. A discussion with Backcountry.com's employee #3 and first and former CMO on the rise and sale of outdoor retailer Backcountry.com, a company that deeply immersed itself in its target customer communities to drive growth.
Key takeaways include:
The importance of maintaining a sharp, differentiated brand identity even as a company scales, rather than chasing growth at all costs. Backcountry's laser focus on its core outdoor enthusiast customers was critical to its success.
Lessons in tying marketing initiatives directly to revenue impact, rather than just engagement metrics. Backcountry had to justify every new program to its founders.
The challenges facing the broader outdoor industry in remaining investable, as rapid pandemic-driven growth has given way to more fragmented, niche-focused competition.
Parallels to the B2B SaaS space, where companies must carefully balance enterprise ambitions with maintaining a differentiated value proposition.
For CMOs looking to build passionate, loyal customer bases in competitive markets, this episode offers a wealth of real-world examples and principles to apply. The speakers' first-hand experience building Backcountry's brand and culture provides a unique perspective.
On last week's Meta earnings call, Zuckerberg reported that demand for the Ray-Ban 'Smart Glasses' was “...still outpacing our ability to build them.”
Either demand is through the roof (not seeing it), or the capacity to produce them is still developing (likely).
Regardless, it appears optical-based assisted intelligence is here to stay in one form or several.
On Episode 51 of the SaaS Brand Strategy Show, Dustin and Mike dig into the recent acquisitions and investments in and around the emerging category, including:
Luxottica's acquisition of Supreme for $1.5 billion and Meta's investment in Luxottica
The potential strategic rationale behind these moves, such as gaining access to digitally native consumers and the metaverse
Concerns about VF Corp's ability to maintain the authenticity and appeal of acquired brands like Supreme
The importance of staying connected to a brand's core community and maintaining its "soul" as it grows
The role of wearable technology and personalized AI experiences in the future of consumer engagement
Is the Face Tech category a true complement or the latest turn on, tune in, drop out distraction?
In this episode of The SaaS Brand Strategy Show, hosts Mike Geraci and Dustin Robertson are joined by Adam and Teymour from DashLX to discuss the challenges and successes of introducing a new category into the market, specifically focusing on the concept of "Lived Experience (LX)" data in the sales process.
Adam and Teymour share their journey from inception to successful sales, providing insights into when and where category strategy helps and where and when it can be an impediment:
- The challenges and benefits of defining and selling a new category, "lived experience" data.
- Practical approaches to integrate the new category into existing market demands and budget structures.
- The concept of 'zero-party data' and how trusted relationships with customers create a access to a new category of data previously unavailable.
DashLX's Lived Experience (LX) category strategy provides a unique and compelling narrative and vision that differentiates Dash LX from competitors, allowing them to secure large contracts and build a trusted relationship with customers. However, when potential clients are more focused on immediate, transactional needs rather than the long-term vision, Teymour and Adam have to balance the aspirational aspects of category creation with practical, short-term solutions that meet current market demands.
A conundrum regardless of what category you work and play in.
Apple recently made some big waves in the AI space. We'll discuss their strategic positioning with "Apple Intelligence AI" and the introduction of a privacy-focused "Personal Intelligence System." We'll explain what this means for the future of AI and what it might tell us about Apple's vision for personal technology.
Remember when machine learning was supposed to change how we did business?
Machine Learning within an organization never materialized except for the largest enterprises with the largest data sets.
Large Language Models (LLM) are delivering what machine learning never could.
Build a Small Language Model (SML) and be blown away at what you can do with very little data.
Shoutout to Kyle Coleman. As far as I know, he coined the term SML.
Episode 48 of the SaaS Brand Strategy Show dives into SML and how everyday AI tools can be strategic, not just automate tasks.
On this week's episode of the SaaS Brand Strategy Show, Ryan, Mike, and Dustin delve into HubSpot's recent acquisition of Clearbit. A move that is part of what's been a significant shift in HubSpot's strategy over recent years, from a focus on inbound marketing to a broader customer management approach. We explore how Clearbit's data enrichment tools can impact customer's CRM and marketing strategies, enhancing lead generation and customer insights—and how this purchase does and doesn't position Hubspot against Salesforce.
Join us as we analyze HubSpot's potential motivations behind the Clearbit acquisition and its impact on the SaaS marketing landscape. We discuss the fine balance between being specific enough to be compelling and generic enough to encompass a wide range of services in your messaging and positioning. And, how does HubSpot's evolving narrative align with the principles of effective category design, and what does it mean for their future, and the future of SaaS marketing?
Tune in this week for an insightful conversation on SaaS marketing, on The SaaS Brand Strategy Show.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
On this episode of The SaaS Brand Strategy show, we kick off a critical analysis of the world’s first “AI pin” introduced this month by Humane. Not just the pin itself, but the launch, and the combined praise and ire it’s drawn within the tech community. We’ll be discussing features, design, and the philosophy that drove its creation—but even more so whether or not that philosophy is showing up prominently enough in the messaging and positioning of the product for it to matter and make waves.
Join us as we unpack Humane.ai’s product launch strategy, and wonder aloud if the focus on its technical prowess has overshadowed the company’s ability to merchandise the human problem its supposedly there to solve. We discuss whether the balance of innovation and human-centric design, and the messaging of it as a whole, is enough to make what Humane.ai is doing meaningful.
Whether you're a tech enthusiast, a marketing professional, a SaaS founder looking at what to do or what not to do in your own messaging and positioning, or just someone curious about the future of wearable technology, we offer our perspectives on the evolving landscape of AI, its potential impact on our lives, and the crucial nature of telling and selling a story when launching new categories of products and technology into the market.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
In this episode of The SaaS Brand Strategy Show, Eddie Yoon, a renowned author, B2C and B2B marketing consultant, and category design expert, joins us to share his experience in consumer psychology and growth strategies. He highlights the importance of category creation for companies of all sizes, and why knowing your customer (and who your Super Consumers are) is key to selling and telling the right story.
Eddie has authored a variety of marketing books, and aided innovative companies like Keurig and iRobot and his wisdom is both wide and deep. With a shared ethos for how we approach marketing, and maybe even the world, this week's episode offers valuable perspectives on consumer behavior and business success in the context of analytics and category design.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
On this week's episode of The SaaS Brand Strategy show, we dive deep into the captivating story of Klaviyo's decade-long journey to transform the ecommerce landscape—culminating in what's expected to be a massive IPO next week. Today's episode unveils the intertwined relationship between Klaviyo and Shopify, shedding light on why Klaviyo has managed to stand out as the dominant platform for ecommerce email marketing.
We explore the resonating power of customer advocacy, the brand's unique value proposition (or lack thereof), and the challenges and opportunities that lie ahead with its anticipated IPO. We devil's advocate our own position on the importance of differentiation, and look at why Klaviyo has had a simplistic and undifferentiated message for years, and yet continued to skyrocket in growth.
Industry experts are keenly watching Klaviyo's moves and what it signals for the future of ecommerce marketing. Whether you're in the ecommerce or digital marketing space, this episode gives insights into their growth, messaging, positioning, market conditions, and more. You won't want to miss it.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
Strap in, SaaS fans. On this week's episode of The SaaS Brand Strategy show, we're taking a ride into the heart of Front’s category strategy around their Customer Operations Platform. We love finding interesting and well-executed category strategy in the wild, and Front has made waves with their's raising over $200 million in their pursuit of this category, and the narrative surrounding it.
Today, we dive headfirst into their website, dissect their product video, and give you our no-holds-barred take on what we think works and what could use a little polish. We're all about celebrating what we think of as the good stuff that aligns with our process and perspective, while also pointing out the things that we think would benefit from a tweak.
If you're looking to stand out in the SaaS crowd too, tune in to see what we think of their marketing strategy and the of their category approach, plus hear our thoughts on how they could level up even further. You'll walk away with a ton of inspiration, and maybe even a few ideas on how to shake up your own game too.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
In this episode, we dive deep into Databricks' recent acquisition of MosaicML, a staggering $1.3 billion transaction that aims to democratize AI and bring its services to, well... everyone? We'll explore their before and after messaging, the key elements of category strategy in play, and the role of AI in shaping today's software messaging landscape. We also delve into the challenges of positioning AI in an industry that's rapidly expanding and evolving, and worries over reverse differentiation.
Join us as we discuss the potential fracturing of AI models and what this could mean for the future of AI in B2B SaaS as the potential looms for it to be incorporated into tech stacks worldwide. We speculate on Databricks' future strategies, including the buzz around a possible public offering to compete against OpenAI in the future.
With plenty playing out in the AI space, join this squad of seasoned tech veterans, who are also curious about AI's explosive growth, and what it means for all of us. Get all that and more on this week's episode of The SaaS Brand Strategy Show.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co
When evolution occurs, previously accepted nomenclature can become obsolete. So it is with "Remote Work," that charming idea of a distributed office, freed from the constraints of traditional office bureaucracy and politics. But remote from what? With the majority of business meeting invites including a Zoom, or Hangout, or Teams link isn't everyone 'remote', even those in a traditional office space? More importantly, does the term create an us-versus-them dynamic that pits on-prem vs off- against each other?
Ep. 41 of The SaaS Brand Strategy Show tackles the disconnect created by the headless "Remote Work" category. With special guest mischief maker Paul Jones from Bridgio, the DRMG team digs into the threats and opportunities inherent to pre-COVID terminology.
This is the first discussion about what we have termed "Headless categories", category names that have just appeared and been adopted without any really heavy strategic thought behind them. On this episode we discuss the "Fractional Leadership" category. Fractional CMOs, Fraction CIOs, etc...
Is Fractional the correct category name or is there a more appropriate term to capture the comprehensive value provided by top-shelf, um, fractional leaders. (it even feels wrong to say it).
Bridgio CEO Paul Jones brought us the headless idea and joins us to discuss the fractional conundrum. He is well-qualified, as Bridgio is a strategic referral network for start-up brands stocked with, um, fractional talent. (You can get a sense of the direction this conversation takes.)
Thanks to Paul for the excellent topic and interesting insights.
-DRMG
The word community is thrown around a lot when it comes to SaaS companies. Sometimes it's mentioned as a trendy growth tool. Sometimes it's used synonymously with social media. Sometimes it's used to refer to a group of developers coding in the same language, or against the same software. So with all these different definitions—which one is the right one? Which definition of community can you observe and implement in your business to capitalize on the best parts of the concept? And to ultimately grow?
In this week's episode of The SaaS Brand Strategy Show, we dive into the complexity of community. We'll define it, discuss the best way to resource it, acknowledge the difficulties of building it and maintaining it. And ultimately, we'll talk about where community and category collide, and how to make use of community in a way that's most beneficial to the growth and success of any B2B SaaS business.
About DRMG:
SaaS Brand Strategy (SBS) isn’t about the colors you use, or the typeface you choose. It’s about the category you design and the story you tell.
DRMG exists to help SaaS businesses find their magic bullet, load it, and fire it into the market.
The companies we work with come out the other side with differentiation, defined categories, and the messaging to back it up. They’re organizationally aligned, inspired, and ready to tell a better story—and win.
Own the brand that drives demand. With DRMG.
Send us an email at: hi@drmg.co
Learn more at: drmg.co





