This interview is part of a series related to Block Club’s 2025 B2B Tech Brand Readiness Report.
B2B buying cycles are becoming unpredictable. The pressure to adopt AI has eliminated traditional in-market timelines—buyers are making decisions constantly, which means brand needs to be top of mind all the time. In this environment, brand can’t be an annual refresh. It has to be an always-on investment.
Jenna Crane, VP of Marketing at Triple Whale, sat down with the team at Block Club to understand how forward-thinking marketing teams are adapting to this acceleration. Triple Whale, an AI-powered intelligence platform for e-commerce brands, tracks $81 billion in revenue data across 50,000 brands, giving them a unique vantage point on both the challenges and opportunities in today’s market. With an impressive background spanning Dropbox, Drift, and Klaviyo, Crane brings battle-tested insights to the noisy AI space to stand out when everyone claims to have “the next best thing.”
Our conversation explored the structural changes happening within marketing organizations, the investments that actually move the needle, and why human connection is becoming more valuable as AI becomes more pervasive. What emerged was a playbook for building lasting brand equity in an era of infinite noise and instant replication.
Block Club: The competitive landscape is moving faster than ever. How has this changed your team’s approach to brand strategy?
Jenna Crane: It’s just really noisy out there right now, especially in the AI space. Everyone is claiming they have the next best thing. But what’s really interesting is how it’s affecting buying behavior. There’s such immense pressure on teams to leverage AI or risk falling behind that traditional buying cycles are essentially dissolving. There’s less of an in-market timeline, which means you need to be top of mind all the time.
The challenge isn’t just awareness though. It’s about demystifying the hype. Everyone says AI will make you better, smarter, faster, more efficient—but what does that actually mean? We’re focused on educating and reducing that hesitance to try, removing barriers by showing how easy it is. It’s plug and play. You can and should try it right now.
BC: You mentioned community as a big bet. Tell me more about that investment.
JC: There’s really no substitute for bringing people together, especially in person. We had our big user conference in May, and while it’s hard to quantify the exact impact, the engagement was incredible.
People are hungry for sharing, and we’re realizing they don’t want to hear from us as a brand entity. They want to hear from peers who are using the product, how it works for them, how they succeed. Community is how we build those relationships, provide two-way value, and let happy customers share their success stories on our behalf.
We’re even launching an AI community that’s product-agnostic. We position ourselves as thought leaders in applying AI in a business context, especially for retail and e-commerce. We bring together all the thought leaders in that space and create the forum for discussion. We’re not talking about our own brand, but there’s brand association with innovation and real impact.
BC: How do you maintain brand consistency when you’re constantly evolving your product and messaging?
JC: I think of it less from a consistency standpoint and more about balance. As long as we ensure our brand principles and identity stay consistent, I’m not worried. The ratio of product education to brand-level content will always fluctuate depending on who you’re talking to and the context.
For example, our new AI newsletter has the tagline “translating AI into ROI.” That core promise remains consistent regardless of how much product education we’re doing at any given time. It’s about knowing who you are and what you stand for, then keeping that consistent despite the evolving message.
There’s no setting it and waiting to re-evaluate later. It’s a constant moving, evolving, living thing. We make micro adjustments as we watch how the market responds, constantly talking to sales about what’s resonating and tracking social to see which use cases get traction.
BC: What marketing investments have been the biggest needle movers for Triple Whale?
AE: Two things stand out: our unique perspective through data thought leadership and community building.
We have 50,000 brands on the platform tracking $81 billion in revenue data. People are hungry for those insights. They want to know what everyone else is doing? What performs best? What strategies lead to success? We’re leaning hard into that differentiation, providing as much value as possible through unique insights.
We’ve also been investing in building our founders’ thought leadership profiles on social media, and it’s translating directly into inbound. There’s so much AI out there that people want real human perspectives from specific, trusted points of view. We’re doubling down on that human touch.
BC: You’ve brought in an interesting role, an operator to represent your customer’s voice. Can you explain that?
JC: We brought on Bryant Garvin, from Ozlo Sleep and Purple Mattress, as an internal representative of how our target audience thinks. It’s been amazing having him as a sounding board to understand what our customers will find valuable.
I wouldn’t be surprised if we see more of this blending of B2B and operator advisor space. There’s so much noise and so many perspectives that will only get louder. You have to dial in on what’s actually valuable for your audience. If you’re a sales productivity tool, imagine having a former CRO from a company matching your target audience in-house to give product feedback, marketing feedback, to truly speak in the voice of the customer.
BC: As someone who’s worked at companies like Drift and Dropbox, do you see a fundamental shift happening in B2B marketing right now?
AE: Absolutely. I think it’s only going to become more critical as AI becomes more pervasive. As robots take over, real human connection is going to be a prized asset. That’s leading me to invest more in the in-person space.
It really comes down to human relationships, feeling inspired, providing value before you’re asking for anything. It’s the reciprocity principle—giving value far in advance of when you’ll ask for something in return. We don’t do thought leadership just to hear ourselves talk. It’s to drive real value for our customers.
The companies that will win are those that understand B2B is still human-to-human marketing. There’s emotion here, brand attachment, real opportunity for differentiation beyond features. That human element is what creates the moat.
The Triple Whale Brand Playbook: Key Takeaways for Marketing Leaders
In Block Club’s conversation with Jenna Crane VP of Marketing at Triple Whale, several principles emerged for building brand differentiation in the AI era:
- Restructure for integrated impact: Create dedicated functions for emerging channels like influencer marketing while ensuring every team contributes to category leadership.
- Transform data into thought leadership: Your proprietary insights are your competitive advantage. Package them as value for your audience.
- Embed customer voice: Consider bringing in operators from your target market as advisors to ensure authentic, valuable content creation.
- Invest in human connection at scale: Prioritize in-person events, community building, and peer-to-peer platforms.
- Adopt continuous positioning: Abandon annual refreshes for constant micro-adjustments based on real-time market feedback.
- Balance education with inspiration: Help buyers understand practical applications while maintaining aspirational brand principles.
The Takeaway: In a world where AI can replicate features overnight, the brands that invest in genuine human connection, proprietary insights, and community-driven growth will build the most valuable moats based on solid brand foundations.
This interview was conducted as part of Block Club’s research into how B2B brands are navigating the AI transformation. For more insights from marketing leaders shaping the future of B2B tech, follow our ongoing series and download our 2025 report B2B Tech Brands Have Conquered Product. Now What? surveying 60 VPs and CMOs from leading B2B tech companies.