How Calendly Is Using AI to Deliver Without PMs

Galen Low explores how Railsware—the team behind Calendly, Coupler.io, and Mailtrap—is delivering complex, high-impact products without traditional project managers. Product director, Julia Ryzhkova, and co-CEO, Sergiy Korolov, pull back the curtain on a self-managing, AI-augmented, and remote-first approach that’s reshaping how teams can operate at scale without sacrificing speed or strategy.

From asynchronous Slack channels to Figma-driven AI workflows, Julia and Sergiy share tactical examples of how Railsware integrates automation with human insight. They talk candidly about challenges like team insecurity around AI and the real work it takes to embed tools effectively. This isn’t hype—it’s a grounded look at what happens when a team builds a culture of maturity, ownership, and intentional knowledge-sharing.

What You’ll Learn
Why removing traditional delivery roles doesn’t mean removing leadership
How AI can be a force multiplier—but only with strategic oversight
What Railsware’s “guilds and squads” model teaches us about scalable collaboration
How mature teams and public communication norms make AI more useful
The limits of current AI tools and why human judgment still matters

Takeaways
AI augments, it doesn’t replace: Railsware uses AI to generate meeting notes, prep documentation, and even help with user stories—but every output is reviewed by a human who knows the context.

Culture trumps tools: Public Slack channels and documentation habits aren't just best practices—they're the foundation that makes AI effective across a team.

Pair work isn’t just for devs: Railsware applies engineering collaboration tactics like pair work and structured standups across roles—from product to ops—to build trust and accelerate learning.

Hiring for maturity: Self-managing teams start with hiring. Candidates are assessed not just for skills, but for their ability to collaborate and self-direct within a flat structure.

AI still needs a coach: Think of delivery leadership like a football coach—you can win a few games without one, but not the whole season.

Chapters
00:00 - Welcome & Introductions
01:00 - How Railsware Operates Without PMs
05:00 - Structuring for Scale: Guilds & Squads
08:00 - Can AI Replace Project Managers?
11:00 - Culture and Hiring for Self-Management
13:00 - Tactics: Public Slack, Docs, and Note-Taking
17:00 - Pair Work Across Roles
20:00 - AI’s Impact on Knowledge Sharing
25:00 - The Role of a Manager in a Self-Managing Team
28:00 - Rolling Out AI Across the Org
33:00 - From Meetings to Jira: Building AI Workflows
37:00 - Using AI in Product and Data Work
41:00 - AI in Hiring and Evaluation
45:00 - Avoiding the AI Hype Trap
51:00 - AI as a Learning Companion
55:00 - People Still Matter