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Highlights

How Oyster Built a Marketing Powerhouse with Just 12 People

Most marketing teams chase growth at all costs. David took the opposite approach—and built one of the most recognizable brands in global employment with a fraction of the resources.

In a recent episode of Unicorn Marketers, David Gales, Head of Marketing at Oyster, shared how his unconventional journey from lifecycle marketing to leading the entire marketing function shaped Oyster’s sustainable growth strategy. His insights reveal why starting with retention, not acquisition, creates the foundation for scalable marketing success.

The Retention-First Foundation

When David joined Oyster four years ago during the pandemic, remote work felt “almost a little bit too further away.” The company was scrappy, moving fast, but David brought something different to the table—a systems mindset focused on retention rather than rapid acquisition.

“I actually think it set me up for success quite a bit because when you first enter like a fast growing startup that you know, when you first want to move into a fast growing startup like you think it’s like growth at all costs and salt acquisition, but I came in with a retention lens and a systems lens,” David explains.

This approach proved transformative. Instead of immediately scaling paid acquisition channels, David spent his early months “building out all our life cycle stages, building out all our nurture flows to make sure that every single customer that came in was nurtured over time and that we are broadly like spreading more Brand awareness overall.”

The result? Sustainable growth foundations that supported Oyster’s expansion as David evolved from lifecycle marketing to demand generation to heading the entire marketing organization.

Leading with Customer Intuition Over Perfect Data

One of the biggest misconceptions in B2B marketing is that you need comprehensive data before making decisions. David challenges this conventional wisdom, especially for fast-growing startups operating with limited resources.

“I find that the thought of having all the data at a glance, like, for you to be able to use to inform new experiments, to like run new programs and stuff, sometimes you just need to lean in with human intuition and understanding your customers,” he shares.

This philosophy has guided Oyster’s marketing strategy from the beginning. Rather than waiting for statistically significant data sets, David advocates for leading with customer understanding: “I find that, you know, spending too much time and trying to gather data is worse than having like a bad experiment, for example. So I would say, like, sometimes it’s really good to lead with your own intuition and how you understand your customers versus having like a ton of data to inform you.”

The Power of Executive Thought Leadership—With Infrastructure

One of Oyster’s most successful marketing channels emerged from an unexpected source: CEO Tony Jamous’ thought leadership content. But what makes this strategy work isn’t just authentic content—it’s the systematic approach behind it.

“We actually found that Tony’s brand influences quite a few deals in terms of like revenue pipeline. But without us understanding that insight through, you know, deeper data, understanding like multi touch, attribution tools versus First Touch, I think that really opened up like a new world in terms of how multiple different marketing channels can actually influence an opportunity or revenue,” David reveals.

The key insight: executive thought leadership works, but only when supported by proper infrastructure. “He has support on the back end. So we have a full content strategy that’s kind of around it and you know, we really like help Tony and lift him up in that circumstance. So fairly streamlined now. In the beginning it was probably more of a lift for Tony, but now it’s kind of a growth channel for us.”

This systematic approach has enabled Oyster to expand thought leadership beyond just the CEO, amplifying voices across their organization to reach different market segments.

Mining Customer Language for Authentic Differentiation

In the competitive employer of record space, standing out requires more than clever positioning—it demands authentic differentiation rooted in how customers actually experience your product. Oyster discovered this through a sophisticated analysis of customer feedback.

“We ran an NGRAM analysis on G2 to understand what the specific patterns of words that customers would use to describe us. And then we would model that within the messaging that we have across channels,” David explains.

This approach ensures their marketing messages resonate because they’re grounded in actual customer language, not internal assumptions about what sounds compelling. The strategy has proven particularly effective in a space where “making sure that our brand is very much reflective of the way that we treat our customers and also, you know, their team members is really important to us.”

Adapting Category Positioning by Audience Sophistication

Rather than forcing a single category definition, Oyster adapts their positioning based on audience knowledge and sophistication—a nuanced approach that maximizes relevance across different buyer types.

“You know, it’s interesting and I feel it depends on your audience, right? Like you are going to have the folks in, let’s say HR that have been there for a while that actually know what an employer of record is. And then you are going to have like a new generation of folks that are coming in. They’re just like, oh, that’s a global employment platform. That makes sense,” David notes.

This flexibility extends to their broader messaging strategy. For experienced HR professionals, Oyster can dive deep into technical capabilities and compliance nuances. For startup founders new to global hiring, the focus shifts to demonstrating how global employment isn’t as expensive or complex as they might assume.

Building Brand in the Age of AI

As AI transforms search and content discovery, David sees an opportunity for brands that invest in authentic authority rather than trying to game algorithmic systems.

“I actually think this is a really good time to invest in brand and thought leadership. Because brand authority, you know, getting really authentic reviews from folks who are evaluating, you know, purchasing different software products is going to be more and more difficult,” he observes.

This shift has influenced Oyster’s content strategy significantly. “We invest quite a bit in like executive thought leadership, bringing content, really refining our positioning as we hear our customers speak about us, either through, you know, social proof reviews, things of that nature.”

Performance with Purpose

David’s marketing philosophy centers on what he calls “performance with purpose”—driving revenue while building systems that scale sustainably and authentically serve customers.

“My philosophy really boils down to driving revenue while building systems actually scale, but making sure it’s really grounded in how people actually behave, but executed with creative taste,” he explains. “So what I actually mean by that is like, you know, I carry a clue about how things perform but like just as much how they feel.”

This approach manifests in practical decisions like designing for accessibility, creating inclusive messaging for global audiences, and building experiences that convert because they’re “designed intentionally and not just for output and like revenue.”

Lessons for B2B Marketing Leaders

David’s journey at Oyster offers several key insights for marketing leaders building in competitive B2B spaces:

• Start with retention systems before scaling acquisition: The foundation for sustainable growth comes from ensuring every customer is properly nurtured and supported, not from optimizing the top of the funnel.
• Trust customer intuition when data is limited: Early-stage companies benefit more from experiments based on customer understanding than from waiting for comprehensive analytics.
• Systematize executive thought leadership: Personal branding can drive measurable pipeline, but it requires proper content strategy and distribution infrastructure to scale effectively.
• Mine customer language for positioning: The most authentic differentiation comes from analyzing how customers naturally describe your product and value.
• Adapt category messaging by audience: Rather than forcing one positioning, develop multiple narratives that match different buyer sophistication levels.

David’s advice to new marketing leaders reflects this philosophy: “Listen to your customers and lead with intuition and the data will come. I think it’s really important to take risks and test things and all of those things will inform a greater strategy and approach that you can share with others.”

For B2B founders building marketing functions in competitive spaces, Oyster’s approach demonstrates that sustainable growth comes not from chasing the latest tactics, but from building systematic approaches grounded in customer understanding and authentic brand building.

The most telling metric of David’s success isn’t just Oyster’s brand recognition—it’s that a 12-person marketing team consistently punches above its weight class in one of the most competitive B2B categories. That’s the power of starting with retention, leading with customer intuition, and building marketing systems designed for long-term success.