Smallstep’s Content Marketing Playbook: Why Giving Engineers Creative Freedom Led to Enterprise Sales
Most technical content marketing follows a predictable formula: how-to guides, feature announcements, and carefully controlled messaging. But what happens when you throw out the traditional playbook and give your technical team the freedom to write about what truly interests them? In a recent episode of Category Visionaries, Mike Malone shared how this unconventional approach helped Smallstep build both a thriving developer community and a successful enterprise business.
Breaking from Convention
Smallstep’s content strategy emerged from a fundamental insight: technical audiences can spot manufactured content from a mile away. Instead of pushing prescribed topics and strict guidelines, they took a radically different approach. As Mike explains, they gave their team “really broad mandate to just write about what they’re passionate about that’s in this space.”
The results were surprising: “it turns out when you give people that sort of purview, you get really high quality content that’s really interesting and informative and it gets shared and it gets searched and people find us that way.” This organic approach to content creation proved more effective than traditional technical marketing.
Building Authentic Connections
The core of their strategy focused on “be ourselves and be authentic and solve a real problem that people have a real need for deliver this technology that is actually needed in the world and then talk about it and teach it and explain it to people.” This authenticity resonated particularly well with their technical audience.
Their content marketing program became “a tremendous asset” because it didn’t feel like marketing at all. Instead of focusing on product features or company news, they encouraged their team to explore the broader technical challenges and innovations in their space.
From Content to Community
This approach to content marketing naturally fed into their open source community building. With “millions of open source downloads” and tracking that indicates “dozens of Fortune 500 are on our website reading docs for open source,” the strategy clearly struck a chord with their target audience.
The content strategy worked in tandem with their open source offerings, creating what Mike describes as a “big sort of funnel into our commercial offering.” But unlike traditional marketing funnels, this one was built on genuine technical expertise and community engagement.
Converting to Enterprise Sales
Perhaps most surprisingly, this developer-focused content strategy proved effective at driving enterprise sales. The company now handles “six and beginning to sell seven figure deals,” with “over 100 customers taking advantage of various scale offerings on that platform.”
The key was that their content demonstrated deep technical expertise while making complex topics more accessible. As Mike notes, “certificate asymmetric cryptography, all this security stuff seems like it’s an area that a lot of smart software engineers shy away from and maybe don’t specialize in. It feels very baroque and obscure.” Their content helped bridge this gap, making sophisticated security concepts more approachable without sacrificing technical depth.
Lessons for Technical Founders
Smallstep’s content strategy offers valuable lessons for technical founders:
- Trust your technical team to create content they’re passionate about
- Focus on authentic expertise rather than marketing messages
- Use content to make complex technology more accessible
- Build community through genuine technical engagement
- Let enterprise sales grow organically from technical credibility
The success of this approach suggests that in technical markets, authenticity and expertise matter more than polished marketing messages. By giving their team the freedom to explore and explain complex technical concepts, Smallstep built both a strong developer community and a path to enterprise sales.
This unconventional strategy continues to drive their growth as they work towards their larger vision of making “enterprises and large software systems and the Internet as a whole is more secure and safer for everybody.” It’s a reminder that sometimes the best marketing strategy is simply to let your team’s genuine expertise and passion shine through.