The SaaS Brand Strategy Show
The SaaS Brand Strategy Show
DRMG
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.
Ep. 57 - From Cannes to Chaos—CMOs, Creators & the AI Tension
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.
Sep 22, 2025
35 min
Category Design vs. Positioning: Why Story Beats Spin
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.
Jul 29, 2025
40 min
Episode 54 — The “Modern” Trap: Why It's a Lazy Differentiator
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.
Jun 27, 2025
24 min
What SaaS Startups and Home Builders Have in Common
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.
Jun 10, 2025
23 min
Ep. 52 - Building Brands that Stick: Lessons from the Rise and Sale of Backcountry.com
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.
Sep 18, 2024
30 min
Ep 51 - Category lessons from the Supreme, Luxottica, Meta deals
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?
Aug 7, 2024
20 min
Ep. 50 - Why Category Strategy Scares the Sales Team
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.
Jul 26, 2024
24 min
Apple Delivers A Master Class In Category Design with Apple Intelligence
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.
Jun 22, 2024
22 min
Can Ai Be Strategic? Do You Have a Small Language Model?
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.
Jun 13, 2024
21 min
Ep. 47 - Hubspot Acquires Clearbit: Will Their Category Change?
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: ⁠⁠⁠[email protected]⁠⁠⁠ Learn more at: ⁠⁠⁠drmg.co
Dec 13, 2023
42 min
Load more