An early startup competing with Siri had one primary target: BlackBerry. To get the attention of key executives, they bought a billboard directly outside BlackBerry's headquarters, proving a highly-focused and effective guerrilla marketing tactic for landing a single, crucial customer.

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The world of Fortune 500 executives is a small, interconnected community. Rather than casting a wide marketing net, focus all energy on securing one key 'lighthouse' customer. Over-deliver value for them, even if the deal isn't profitable. Their endorsement and introductions to peers are more effective than any marketing channel.

Startups can appear much larger by purchasing the smallest possible unit of a large-format ad (e.g., a Times Square billboard for two minutes), capturing high-quality photo/video, and then amplifying that content across all owned digital channels like LinkedIn and email.

Unlike typical consumer ads, San Francisco's outdoor advertising is dominated by niche B2B startups. They accept that 95% of viewers are irrelevant to reach a high concentration of VCs and tech talent, signaling a strategic return to immeasurable brand awareness over direct-response marketing.

Recent OpenAI billboards in San Francisco feature portraits of startup founders with just their name and company. This campaign is highly insular, targeting an 'if you know, you know' audience within the local tech ecosystem. It highlights a trend of B2B marketing in SF that functions as an insider conversation rather than mass-market advertising.

Marketing a defense company is fundamentally different from marketing a consumer product. Instead of a broad "one-to-all" campaign targeting millions of customers, defense marketing is a "one-to-few," hyper-targeted effort aimed at a small group of influential government decision-makers who could all fit in a single conference room.

To maximize ROI on their out-of-home spend, Float's media buying was highly scientific. They physically mapped the office addresses of their existing customers across the country, identified clusters in cities like Toronto, and then concentrated their billboard buys in those specific regions.

Leading marketers confidently invest in high-cost, low-measurability channels like billboards and physical books. They understand that reaching a concentrated target audience builds brand in a way that can't be captured by direct attribution but drives long-term pipeline.

In every industry, a few established enterprises—like Costco for HR software—act as 'tastemakers' by adopting new technology early. Winning these key accounts first provides crucial validation and influences other companies in the vertical to follow, creating a powerful go-to-market advantage that bypasses smaller customers.

Instead of cold outreach, identify where employees of your target companies gather—like triathlons or industry events. Set up a booth and let them experience your product firsthand. This creates organic buzz and personal testimonials that travel back inside the organization, generating warmer leads than a direct sales approach.

To convince large enterprises to buy from a small startup, you need a two-part "bullhorn" pitch. First, solve an immediate, urgent pain point. Second, frame that solution as the first step on a journey to a larger, strategic destination that the customer wants to reach, justifying the long-term partnership.