Leading SMBs through the AI inflection

Reimagining the software stack for an AI-native future

HubSpot serves millions of small and medium-sized businesses around the world. As AI reshapes how software is built and used, those customers don’t need experiments or demos, they need systems they can trust.

We’re in the middle of a fundamental transformation: rethinking our software stack, product architecture, and engineering practices to build high-quality systems at global scale. This is deep, technical work, and it’s why we’re scaling our Principal and Distinguished Engineering community.

AI isn’t something we’re adding at the edges. It’s changing how workflows are designed, how systems interact, and how decisions are made across the platform.

To lead SMBs through this inflection point, we need senior engineers who can:

• Navigate ambiguity with judgment
• Combine systems thinking with hands-on technical depth
• Help teams move from AI-assisted to AI-native software

That kind of work doesn’t get delegated. It requires experienced technical leadership embedded in the problem.

https://www.youtube.com/watch?v=10aclvmpp3Q

The problems we’re solving

These are some of the challenges Principal and Distinguished engineers are working on today:

• Building agentic systems that are observable, testable, and safe
• Designing evaluation frameworks for probabilistic AI systems
• Balancing rapid experimentation with the reliability SMBs depend on