Growing B2B companies tend to face a common inflection point: transitioning from initially serving startups and SMBs to also moving upmarket to target enterprise customers. This shift is a tried-and-true path based on the promise of more market share, larger deals, and more stable revenue, but it demands a fundamental rethinking of your content approach and brand strategy. A common question that comes up is: How do you adapt your messaging to resonate with sophisticated enterprise buyers without losing your brand’s distinctive voice?
We recently welcomed Jenny Thai, content leader at Vanta, to our Best Story Wins podcast, where we discussed this challenge/opportunity and Vanta’s evolution from focusing on startups to selling to larger organizations with dedicated security teams. What did the brand shift when they discovered the content strategy that worked for founders fell flat with enterprise security leaders? A lot.
If you’re making a play to move upmarket, Thai’s episode is a must-listen, full of knowledge on how do it effectively. Here are our biggest takeaways.
1) Understand the enterprise buyer’s knowledge baseline.
When you’re selling to startups, educational content often focuses on fundamentals—the “101” material that helps founders understand why they need your solution in the first place. But enterprise buyers? They’re well past the introductory stage.
As Thai points out, the security leaders Vanta needs to target already understand compliance basics. What they need is high-level insights that match their expertise level and address the complex challenges they face daily.
2) Level up your thought leadership.
So how do you create content that resonates with more sophisticated buyers? It starts with a strategic shift in your thought leadership approach.
- Partner with subject matter experts—both internal and external—to tap into specialized knowledge that enterprise buyers value.
- Focus on advanced challenges rather than entry-level concepts.
- Address the specific conversations happening among senior leaders in your target vertical.
- Demonstrate credibility through sophisticated analysis and insights.
For Vanta, this meant moving beyond “What is compliance?” content to tackle nuanced discussions around trust management, proactive risk assessment, and integration challenges that security leaders face in larger organizations.
3) Balance brand distinctiveness with enterprise appeal.
One of the trickiest parts of moving upmarket is maintaining brand personality while establishing credibility with more conservative enterprise buyers. Vanta faced this creative challenge head-on and took a hard look at how a new audience might perceive core brand elements (like their purple llama mascot).
The key is to maintain a distinctive brand voice and tone but take more opportunities to reassure people that you’re a credible reliable partner. That means you have to garner trust at every touch point.
- Showcase your largest customers. Thai says Vanta incorporates customer quotes from their large customers into multiple pieces of content. This social proof signals to enterprise prospects that companies like theirs already trust you.
- Highlight scale and growth. “We reiterate the fact that we now have 10,000 customers globally,” Thai says. Demonstrating your scale helps enterprise buyers feel confident in your stability and capacity.
- Create content continuity. Repetition is the key to enterprise-ready positioning. For example, Vanta uses those customer quotes and the 10,000 customers stat to reinforce their profile throughout various pieces of content.
- Evolve your research and resources. Vanta launched their annual State of Trust report to demonstrate thought leadership at a scale that enterprise buyers expect. The report, which surveys security and business leaders and shares key industry trends, is now a flagship piece of content that positions Vanta as an industry leader. (It also provides marketing campaign material for a year.)
How do you know these moves are working? While it can be tough to measure the overall efficacy of a content strategy shift, there are signals to watch for:
- Industry adoption of your terminology and frameworks.
- Analysts beginning to use your language.
- Enterprise customers articulating your value in the way you’ve positioned it.
Success often comes down to a gradual perception shift. But just remember that repetition is the most effective way to tell a cohesive, consistent story that will move decision-makers down the buyer journey.
Your Next Steps to Make the Upmarket Shift
Remember that moving upmarket is a marathon, not a sprint. If you want to shift your content strategy upmarket, start with these key moves.
- Audit your current content to identify what’s too basic for enterprise buyers.
- Interview your existing enterprise customers to understand their knowledge baseline.
- Map the specialized topics that matter to senior decision-makers.
- Identify credible subject matter experts who can elevate your content.
- Test different content formats that signal enterprise readiness.
Just be patient with the results while remaining consistent in your approach. As Thai says, “Remember that brand is a long-term play.”
So, if you’re ready to learn more about evolving your content strategy, measuring brand impact, and balancing distinctiveness with credibility, check out our full conversation with Jenny Thai on the Best Story Wins podcast.
