What might this outreach approach look like for me?

#31 · How to Build AI Automation Offers (One-Time + Recurring)

What might this outreach approach look like for me?

I’d suggest creating a short Loom video that you send directly to the prospect. Start by finding a post on my Instagram, then record a quick 30‑second video in the bottom‑left corner of the screen. Introduce yourself, explain that you’re a real person, and show the value you can provide—how you could save them money or generate revenue. Keep it concise, make it feel personalized, and end by saying you’d love to work together because your values align. Ask them to respond with a thumbs‑up or a quick "yes," and include a link to your calendar so they can schedule a call. The key is to appear authentic, respectful of their time, and to avoid sounding like a generic robot or spammy outreach.

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Can you explain step‑by‑step how sending Loom videos in outreach works?

Sure, here's how to use Loom videos in your outreach. First, record a Loom video—either on the prospect’s website or on a private social media profile after you’ve spent time researching who they are. Make it clear that this isn’t random spam; introduce yourself, explain why you matter, and provide social proof. Then describe the specific value you can deliver, such as identifying an under‑utilized part of their funnel and showing a quick fix that could add significant revenue. End with a soft ask, like asking them to respond with a thumbs‑up if they’re interested in seeing more ideas.

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Do you have a blueprint or system for structuring a custom Loom outreach video?

Start the Loom recording on the prospect’s actual profile or resource page so the first frame shows their profile, not a cover page. In the first few seconds, add a quick zoom to prove it’s not a templated video. Spend the opening 15‑30 seconds talking about them—position the video as providing value, not a sales pitch. Drop social proof organically while you explain, rather than dumping it all at the start. For the call‑to‑action, keep it low‑friction: ask for a simple thumbs‑up and promise to deliver the full action plan, templates, and any needed work for free; only if they love it do you discuss a deeper collaboration. This approach makes it seem you’ve uncovered an opportunity they’re missing, gives them the fix, and lets them choose to work with you because you’re providing value, not forcing them.

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I’ve built an automated personalized outreach system but have almost no credibility. How should I market my system?

Even with zero credibility you can still get traction by using a conversational tone in your outreach. Write longer, personalized emails that give context about who you are, what you’re building, and why you’re reaching out. Make it sound like a genuine conversation rather than a sales pitch. This approach works well for beginners because it feels authentic and helps you stand out from the generic offers flooding inboxes. Give it a try – the personal, story‑driven style often lands the first leads when you don’t have a brand reputation yet.

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When we get a reply from a prospect, should we pitch them on a sales call immediately or ask some questions and build rapport before sending a scheduled link?

Yes, you should pitch them on a sales call immediately. When a prospect replies on Upwork, they often ask follow‑up questions like, “Hey Pete, I liked your video. Can you do this for X amount? Can you do it this way?” If you give them all the information in the reply, there’s no incentive for a call—you’ve already proved everything in writing. A call lets you demonstrate how you differ from the sea of generic Upwork freelancers. The best approach is to lightly address their questions in your reply, thank them, and then suggest a short 15‑minute call to go over details and provide a scoped price. Offer a few time slots (e.g., next hour, 4 p.m., 6 p.m.) and include a calendar link so they can pick what works for them. This way you keep the conversation moving and avoid endless back‑and‑forth. I also provide multiple ways for them to get in touch—email, calendar link, and other contact options—so they can choose the method that’s most convenient.

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