AI-first Software Development and the Evolution of Developer Experience and Enterprise Software
Lessons from Boldstart Founder Summit 2025
This year marks my third at the Boldstart Founder Summit. It's remarkable how much has changed from year-to-year, both for myself and our startup (CodeYam), the other founders, and the technologies we're building each day.
While last year AI-curiosity was a strong theme, this year everyone was sharing learnings and how they've adapted how they build software and, in some cases (like ours), what they're building to leverage the superpowers AI can provide for software development.
This year's format was an unconference with experienced founders hosting off-the-record discussions on prevalent themes.
Without getting into the off-the-record nitty gritty details, there were four categories that stood out to me in terms of the topics discussed:
The Evolution of Developer Experience
AI’s Transformation of Software Development Workflows
Product Comes First. But What About AI Agents as Users?
Business Insights for Technical Founders
1. The Evolution of Developer Experience
Developer experience (DX) is no less important in the age of AI-native software development. In fact, it might be more critical than ever.
Thinking "they're technical, they'll figure it out" about your users is a bad assumption, and you're likely radically underestimating how long it takes developers to onboard to your product or tool.
There's a lot to be gained from observing first-time users of your product and where they get stuck or hit bugs. While eating your own dogfood and testing your product is important, it's insufficient. It sounds silly, but a new user is only truly new once – and observing them is the highest-fidelity way to understand how to improve your onboarding experience.
The concept of "death by 1000 papercuts" resonated deeply when you think of a product you hate using, but aren't really sure why. The same is true for the products you're building; each small moment of confusion adds up and leads to a negative user experience and churn.
I've long been a fan of qualitative testing and using processes like GV’s Design Sprint and Michael Margolies’ methodologies to increase learning velocity. The benefits of user research and recording and/or watching users engage with your product, paired with AI tools to make data labeling and synthesis more efficient, cannot be understated.
Founders shared a lot of creativity not just around their own products but the tools they use. This was especially true for AI code generation and prototyping tools, of which there's been a Cambrian explosion that is challenging for even the most AI-embracing early adopter to keep up with today.
2. AI’s Transformation of Software Development Workflows
Every single founder I spoke with uses multiple AI tools today to help them build software. For some, this is primarily AI tools to help them write code such as Cursor, Cline, Codebuff, or Windsurf. Others are experimenting with AI editors like Zed or design-to-code experiences like bolt.new, v0, or lovable. Devin has great UX, but for the most part left a lot to be desired in terms of utility.
Still, even with the limitations or challenges of certain AI tools, many founders called out a "capabilities explosion" that has expanded the role of developers. "The role of product has completely changed," folks agreed, and the feedback loops from design to prototype to development to deployment have the potential to be tighter than ever before.
And if you're not taking advantage of the velocity boosts these tools can provide, you can bet your competition is. While there wasn't consistent agreement on what the ideal future of software development looks like, there was certainly consensus that how we're working needs to change – and for everyone in the room, likely already has.
Some see the future as orchestrating code, and ideas that once seemed silly or impractical now seem possible – although it's hard to say on what timeframe.
"Vibes" are also in, and vibe coding while using AI, while it has risks, is increasingly popular, especially for newer developers. Seasoned technical leaders, like keynote speaker Scott Yara, also are excited to return to writing code with AI.
3. Product Comes First. But What About AI Agents as Users?
In Scott's keynote, he reflected on decades of experience as a founder and technical leader. One of the things he said that most stood out to me was that "Product comes first" and that building something special is hard – so ask yourself, why is your product going to be special?
In terms of AI products, what does truly great look like? Waymo and ChatGPT are exciting examples, but we're still so early, and Scott suspects that more truly great AI software products are yet to come.
What we're building and how we're building is changing with AI. But so too, observed a few founders, is the demographic of our users. We're going from B2B and B2C to B2A (business to agent) and, eventually, maybe A2A (agent to agent). Thinking about how agents and AI indexes, finds, and uses your product is likely going to be increasingly important.
And it's early innings. A few founders have built developer tools recommended by AIs (e.g., Claude) but there are challenges – e.g., if an older version is recommended, or a newer version is not supported by models that your human customers are using to ask questions or debug.
Building for a future where humans, humans using AI, and AI agents are all using your product is increasingly important. But so is context. If something is mission-critical, it's likely that you're going to have a human-in-the-loop; e.g., nothing getting merged into a code base without a human review. On the other hand, in areas where there's lower risk to more truly agentic agents acting autonomously, there's room for more complete automation with less supervision – although still with appropriate boundaries and guardrails. Security is paramount.
This got me fired up thinking about what we're building at CodeYam, and how we are leveraging software simulation to give human users confidence in code changes. Making it easier to identify and address unintended side effects and bugs, regardless of if it's humans or AI generating the code (or some combination), is valuable.
4. Business Insights for Technical Founders
Boldstart optimizes for visionary technical founders, so it comes as no surprise that a lot of the teams are building products that are on the cutting edge of technology and AI today. When it comes to things like pricing, sales, partnerships, and enterprise adoption, there were a lot of hard-won learnings shared.
Without spilling anyone's secret sauce, I think it's important to call out that for enterprises, there's a dueling pressure to adopt innovative AI tools that can help their businesses but also still often fear working with startups. While some founders observed that, when sufficiently motivated, enterprise deal speed can move a lot faster than in the past, there are still hurdles.
One founder observed that "you have to sell the future like it's the past" – meaning fit into old paradigms for buyers while still delivering something new and better than what they bargained for. Backwards compatibility can act like a bridge that gets you into their stack and, once you've proved your value, you can land and expand your offering from there. Really proving out your value to potential customers early-on is critical.
E.g. Eliot Durbin’s observation on X:
Even in sales and partnerships, thinking about your learning velocity is crucial. Your learning rate "needs to exceed your competitors." Think of pricing as a product, and aim to learn and experiment accordingly.
Make sure you're defining, and measuring, the right metrics and you're focused on delivering value first.
Conclusion
What struck me most was how these themes interconnect: we're building the future of AI-native software development while we're exploring it as a room full of builders, which is simultaneously exciting and chaotic.
Velocity, as Ed Sim highlighted so effectively in his X recap, is essential.
The only thing I'm sure of is that next year's Founder Summit is going to be radically different from this year's, and I can't wait for how much I – and every other founder, builder, and operator – will have learned and built between now and then.
Thank you to Ed, Eliot, Ellen, Shomik, Ernest, Ron, Charlotte and the boldstart team and partners for bringing us together for these action-packed discussions. Thank you as well to the founders who led and joined sessions, shared insights and learnings, and were radically open about what’s working and what’s challenging today.
The sessions hosted by folks like Steve Manuel (Dylibso), Ian Jennings (Testdriver), João Moura and Rob Bailey (CrewAI) were incredible. I learned so much and left inspired.