S1E2 -- September 18, 2025
He's Running His Marketing Department With 40+ AI Agents.
with Jacob Bank

About this episode
What does it look like when a former Google PM director builds the productivity tool that does the work for you, not the one you go to do work in? Jacob Bank founded Timeful, sold it to Google, ran product for Gmail and Calendar, then left in 2021 to build Relay.app. After four years of evolving from collaborative to-do list to automation tool to AI agent platform, Relay is now framed as an AI employee company. He runs his own marketing function with himself and 40+ AI agents. In this conversation, he breaks down why 'connect calendar and Monday' is the wrong way to prompt an automation tool, why job descriptions are easier to write than workflows, and what kinds of work will and will not be replaced as AI employees get more capable.
Key takeaways
- The next productivity tool does work for you, not the place you go to do work. That reframe is the unlock behind Relay.app.
- Write job descriptions, not workflows. People are better at describing the work they wish someone else would do than at flowcharting the steps.
- AI employees are not human employees. Don't make them mimic humans. They're better at instant, parallel, never-forget work and worse at authenticity and connection.
- Marketing channels are bifurcating. SEO slop and spray-and-pray outbound will lose. Word of mouth, personal trust, and educational content win.
- Headcount conversations get a third option. Reprioritize, hire, or delegate to AI. The starting question (what would this person actually do?) is unchanged.
- Real-world jobs are safest from AI. Childcare, nursing, plumbing, the trades. Knowledge work has more to figure out.
- Operate from the assumption your job will look totally different in three years. No one knows exactly how, so invent it before someone else does.
Chapters
- 00:00Introduction to Jacob Bank and His Journey
- 03:24The Evolution of Productivity Tools
- 06:02The Role of AI in Workflows
- 09:07AI Agents and Their Impact on Small Businesses
- 11:49Understanding AI Employees vs Human Employees
- 15:06The Future of Work and Human Skills
- 16:18Navigating the AI Landscape
- 18:53Building AI Solutions for Business Needs
- 21:43Final Thoughts and Future Directions
Notable quotes
- "We can create a productivity tool that isn't a place where you go to do work, but something that actually does work for you on your behalf."
- "An AI employee is not the same as a human employee. You would not give the exact same jobs or the exact same guidance."
- "If AI is going to take the version of your job that exists today, what's the new version? Start doing that."
- "Operate from the assumption that your job will look totally different three years from now, but no one knows exactly how, so put some time and effort into inventing it. Otherwise, someone else will invent it for you."
- "What would the new hire actually do, and how would that help? In the new world you have a third option for that question: AI."
About Jacob Bank
CEO and founder of Relay.app, an AI employee platform for small businesses. Former PM director at Google leading product for Gmail and Calendar. Founded Timeful (AI-powered calendar) which was acquired by Google in 2015. PhD researcher at the intersection of AI and time management before founding Timeful.