Since moving back to San Francisco at the beginning of last year, I’ve been hosting regular founder dinners. Last night, I hosted a design-focused dinner where we dove into topics arounds building developer brands and thoughtfulness of user experiences. We were fortunate to have two wonderful guests and good friends of mine: Cris Dobbins, VP of Design at Cleanlab, and Jake Cooper, CEO of Railway. While I expected them to share a few insights before everyone broke off into smaller conversations, something remarkable happened. The discussion naturally flowed for two straight hours, with everyone contributing thoughtful insights, questions, and lessons learned.
I wanted to share some of the takeaways from this engaging evening. These insights are for founders earlier in their company journey.
Design Matters More Than Ever
Twenty years ago, we were creating WordPress websites with drop shadows and Flash animations. Today, everything needs to look polished — unless you’re Ilya Sutskever, who can raise $1B with a simple text-based website for Safe Superintelligence Inc! Just yesterday, three AI companies — Harvey, Poolside (announcing a $500M raise), and Mintlify — made announcements about their refreshed branding and messaging. Similarly, when MemGPT announced their Seed funding two weeks ago, it came with a new name and a sleek brand.
The importance of design and branding can’t be overstated. Authentic brands often reflect their founders’ personalities. For example, Sentry’s brand embodies David Cramer, and HashiCorp’s brand is a blend of Mitchell Hashimoto and Armon Dadgar. If design isn’t your strength and you’re unsure how to hire for it, outsource the work. Hiring an agency to create a brand guide, then bringing on a junior designer to maintain it, can be a game-changer.
Design is More Than Colors
During the dinner, Cris Dobbins emphasized that a brand goes beyond logos, colors, and typography. While those elements play an important role in visual identity, they are only the surface-level components of a brand. A brand goes much deeper — it’s a feeling, an experience, and a relationship that exists between your company and its audience. It’s about how your business is perceived by users and customers in every interaction they have with you.
“Brand is your values.” — David Cramer, Sentry
Consider your brand’s tone, vibe, and messaging. How do you want to be perceived? At HashiCorp, we always aimed to be polished, professional, knowledgeable, and approachable. This consistency translated across everything we did — branding, messaging, marketing, and sales. We built trust with our customers and never compromised on quality, like avoiding gimmicks at our conferences and ensuring our blog posts were technical and insightful.
Brand is Content
A surprising takeaway from the evening was how often founders mentioned the importance of technical blogs and content as core components of a company’s brand. For companies building products for technical audiences, content doesn’t just support marketing — it becomes a direct extension of the brand itself.
When your audience is developers, engineers, or other technical professionals, they care about the depth of knowledge you share, the problems you help them solve, and the value you bring to their work. Technical blogs, whitepapers, tutorials, and open-source contributions all play a vital role in building trust and authority. Every piece of content you create reflects your brand’s values, expertise, and tone.
Companies like Stripe, DigitalOcean, Datadog, and HashiCorp have grown their brands through rich libraries of tutorials, case studies, and thought leadership articles that have stood the test of time.
In short, if you’re building for a technical audience, content is more than just a marketing tool — it’s a foundational part of your brand. The companies that win in this space are the ones that deliver continuous value through educational, insightful, and relevant content.
You Have 3 Seconds to Capture Attention
Jake Cooper from Railway often emphasizes the importance of capturing someone’s attention in just a few seconds. In a world where users are constantly bombarded with information and options, it’s gotten even crazier with AI, attention spans are shorter than ever. Users quickly judge a website based on their first impression, and if it doesn’t immediately engage or guide them, they’re likely to bounce and move on to something else. This makes those first few seconds crucial for both capturing attention and creating a seamless user experience. The advice is to dedicate significant time and effort to refining the user experience to make it as intuitive and engaging as possible. From the moment someone lands on their website, the next step needs to always clear — whether it’s signing up, exploring features, or actually being able to sign up for the product without filling out a long form for access.
I wanted to say a huge thank you to everyone who joined the dinner: Akshay Chalana and Oscar Avatare founders of Saphira AI, Ankita Gupta founder of Akto, Amrutha Gujjar founder of Structured, David Cramer founder of Sentry, David Crawshaw co-founder of Tailscale, Dan Robinson founder of Detail AI, Devin Stein founder of Dosu, Jonathan Mortensen 2 time founder building an AI stealth company, Maria Grineva CEO at Prog AI, Sethu Meenakshisundaram co-founder of Zluri, and Shantanu Joshi founder of Saavy.
