leadwithai pro

Stay ahead of AI. In less time.

Expert briefings, live sessions, and a peer community, so you always know what matters. And more importantly, what you can safely ignore.

AI is moving fast. Most of it isn't worth your time.

The leaders who stay ahead aren't the ones reading every newsletter or testing every tool. They're the ones who know what to pay attention to, and what to let pass.

Lead with AI PRO exists to give you exactly that edge.

A weekly briefing that cuts through the noise, live sessions with practitioners who share what's actually working, and a peer community of senior leaders figuring it out alongside you.

Sharp, current, and designed to fit your schedule, not take it over.

Stay CURRENT without the overwhelm

A weekly newsletter and two monthly live briefings cut through the noise (one on the latest AI tools and platforms, one focused on agentic AI) so you always know what matters, and what you can safely ignore.

Stay SHARP with bi-weekly Masterclasses

LIVE and on-demand access to Masterclasses with world-class guests, like the Chief People Officer of OpenAI, the CHRO of Zapier, and NYT bestselling authors like AJ Jacobs, so you learn from the best, on your schedule.

Stay CONNECTED with global peers

Every month, fellow senior leaders demo the AI assistants they've actually built, from research tools to automated workflows. Plus lifetime access to our executive WhatsApp community, where real use cases and tool updates are shared daily.

Less than one hour of consulting. For a full year of staying current.

Start with a 14-day trial for $1. Full access from day one. Cancel anytime.

Lead with AI PRO
$29/Month
Weekly AI briefing: what matters, what to ignore
Live expert sessions every week (all recordings included)
Peer community of senior leaders
100+ on-demand lessons & playbooks

Next PRO Events

Stay ahead with exclusive events designed for executives. Join industry leaders for in-depth discussions on the latest trends in AI, technology, and business innovation.

Demo Day: AI Leader Advanced Cohort 8

August 28, 2026
The best way to understand AI isn’t through theory, it’s by seeing how people are actually using it. In this session, leaders will share real use cases they’ve built during the cohort, from simple workflows to more advanced setups.

Executive Briefing: August

August 27, 2026
AI is changing too quickly for leaders to track everything themselves. Join this Lead with AI PRO Executive Briefing with Daan van Rossum for a curated breakdown of the AI shifts that matter most for leaders right now.

ChatGPT Work: We can now give ChatGPT a job to do

August 5, 2026
In this month’s Agentic Briefing, Gary C. Tate will use a straightforward example to show the difference between Chat and Work. He’ll demonstrate how project context, skills, connectors and scheduled tasks can support a piece of work all the way through to a brief, presentation or shared site.

Frequently Asked Questions

I'm already drowning in AI content. Why is this different? Most AI content is written for enthusiasts, not executives. It covers everything, which means it's useful to almost no one with a real job. Every week, we cut the noise down to the three things that actually matter for senior leaders, and tell you what you can safely ignore. Instead of telling you what happened, Lead with AI PRO tells you what it means for how you lead, and gives you a community of peers to pressure-test that thinking with.

Is this for people just starting out or people already deep into AI? Both, genuinely. If you've completed AI Leader Advanced, PRO keeps your edge sharp as things evolve. If you're earlier in your journey, the community and sessions give you a fast track, you learn from people already two steps ahead.

I'm not technical. Will I be lost? This is built for non-technical leaders. No code, no jargon, no assumption that you're keeping up with the tech. The whole point is that you shouldn't have to be technical to lead confidently with AI, and that's what every session, briefing, and community conversation is designed around.

How much time does this actually take per week? As little as 5 minutes if you want. Read the briefing, skim what's relevant, done. The live sessions are an hour and always recorded if you can't make it. The community is there when you want it, not a firehose you have to keep up with. Most members find it saves them more time than it costs.

What makes the community different from LinkedIn or a Slack group? The people and the standard. This is a private group of senior leaders who are actively building with AI, not broadcasting opinions, not selling something. Members share what they're testing, what broke, what worked, and what just launched that's worth paying attention to. It's a peer group, not a feed.

What happens after the 14-day trial? You're automatically moved to the plan you chose, monthly at $29 or yearly at $290. You'll get a reminder before the trial ends. Cancel anytime before that if it's not right for you.

Can my company pay for this and are there team or group options? Yes, we work with organizations on team memberships and organization-wide programs. Get in touch to discuss what makes sense for your team size.