Uploaded December 2025 | Updated September 2026, 3 days ago
Conner Simmons, from WorkOS, sits down with Forrest Brazeal to unpack a hard truth about building modern software: AI has made it easier than ever to ship product but trust is still the real bottleneck when moving upmarket.
They explore how today’s startups can “vibe code” their way to impressive demos and fast growth, yet still struggle to sell into the enterprise. The reason? Enterprise readiness isn’t about features, it’s about trust, security, identity, and getting foundational decisions right the first time.
Topics covered include:
• Why AI lowers the barrier to building software but not to earning enterprise trust
• The risks of “vibe coding” critical infrastructure like auth and access control
• Why security, IAM, and multi-tenancy are bedrock decisions you don’t get to redo
• How fast-growing AI companies are moving upmarket sooner than ever
• The difference between reinventing the wheel and “unsolving” solved problems
• Why trust, governance, and guardrails matter even more in an agent-driven world
A candid discussion on why you can’t vibe trust and why building enterprise-ready foundations early is essential for scaling modern software companies.
Conner Simmons, from WorkOS, sits down with Forrest Brazeal to unpack a hard truth about building modern software: AI has made it easier than ever to ship product but trust is still the real bottleneck when moving upmarket.
They explore how today’s startups can “vibe code” their way to impressive demos and fast growth, yet still struggle to sell into the enterprise. The reason? Enterprise readiness isn’t about features, it’s about trust, security, identity, and getting foundational decisions right the first time.
Topics covered include:
• Why AI lowers the barrier to building software but not to earning enterprise trust
• The risks of “vibe coding” critical infrastructure like auth and access control
• Why security, IAM, and multi-tenancy are bedrock decisions you don’t get to redo
• How fast-growing AI companies are moving upmarket sooner than ever
• The difference between reinventing the wheel and “unsolving” solved problems
• Why trust, governance, and guardrails matter even more in an agent-driven world
A candid discussion on why you can’t vibe trust and why building enterprise-ready foundations early is essential for scaling modern software companies.
