Selling AI to Agents Part 1: Ray Wood

Ray Wood has been around long enough to know what works with agents, and what doesn’t.The Aussie-Canadian direct response veteran behind AI Ad Machine has used every outreach tactic in the book. Cold calls, one-on-one calls, high-end sales presentations.But he’s finding that sometimes, agents want less personal attention.Here’s what Ray’s learned about reaching agents in 2025, plus the testing strategy that’s letting him run 100+ ad variations simultaneously.Here are the Non-Obvious Insights from our Conversation…Group-First, Low-Pressure Offers are Beating 1:1 Calls Right Now.“I reach out [to agents] and say, ‘Hey I’m doing this and this, why don’t we jump on a call?’ ...May or may not get a response. If I say I’m doing a free training...I get much more buy-in.”It’s high-leverage, maximized opt-ins, and he can qualify leads by engagement. Reminds me of how Josh Smith’s virtual workshops are performing well for him this year.Experiment with Newsletter Platforms to Get More Results from Your Email List.“So what I’ve done is I’ve created some content and then built a link, which has got a [Substack] subscribe button and I’ve sent that out to my list. I think in two weeks, I’ve had a couple of hundred people opt-in from a 28K email list. For normal day-to-day, I’m using Kajabi. I’m familiar with it and that’s where all my contacts are. So that’s what works for me.” - Ray WoodStill early days, but I love that he’s testing this. Newsletter tools like Substack or BeeHiiv tend to have better deliverability over tools like Kajabi. Any tool that caters to the info marketing or course creator niche will have above-average unsubscribe rates, which hurts deliverability for all their users.Ruthless A/B Testing Beats Intuition Every TimeRay’s tool runs 40-100 different ads simultaneously and kills the losers within 10 days.“With the Ad Machine, I can run a set of 40, 50, 100 different ads. And after 10 days, I can monitor which image is working, which copy’s working, which headlines working... and then I can continually focus on that”.It’s a good lesson for any leader…Never fall in love with your own messaging ideas or clever copy.It’s better to create 100 imperfect campaigns and let agents tell you which ones work. Double down on what works, and ruthlessly cut the rest.So let’s sump up the core principles I take from Ray’s playbook:* Test everything, assume nothing - Run multiple variations simultaneously and let data decide* Lower the barrier, raise the value - Group trainings feel safer than sales calls while delivering the same qualification* Own your audience - Build on platforms where you control the relationshipWant to go deeper?Click to listen to the full conversation with Ray Wood. Or search Real Estate Thought Leaders on Apple Podcasts and Spotify.Hit Reply and tell me what you’re seeingWhat’s working for tech founders and innovators to reach agents?Where could they sharpen their messaging and get more effective?Ask This:When was the last time I tested my assumptions about my audience?What simple test could I run that would generate useful, non-obvious insights to improve my marketing?Quick Links & ResourcesRay Wood’s AI Ad MachineThanks so much to Ray for opening up his marketing playbook. Make sure you reach out and connect with him, nothing beats his Aussie positivity and direct response mentality!-MattAgency Founder & Author of MicroFamousPS Here are two ways I can serve you…90-Day Strategy Sprint - We’ll work together to make the critical decisions on your marketing and content strategy. Then we’ll translate those decisions into new rituals and habits, and get your entire team on board.Done-for-You Content Service - From Michael Maher and Lars Hedenborg to Jeff Cohn and Marki Lemons-Ryhal, my content team has served many of your fellow real estate leaders. We turn conversations into newsletters, podcasts and videos, all with zero hassle. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit rethoughtleaders.substack.com