u/chandlerbing006

I Built a LinkedIn Outreach System That Actually Started Conversations Instead of Looking Like Spam

Built a LinkedIn outreach workflow yesterday and got 4 positive replies on day 1.

A few weeks ago I posted about wanting to build AI systems publicly and got called out because I was mostly talking instead of executing. Fair criticism honestly. So I spent the last few weeks building a LinkedIn outbound workflow focused on keeping humans in the loop instead of fully automating conversations.

The system handles prospect scraping, personalized connection requests and messages, reply tracking, automated follow ups, and Slack notifications when someone responds positively so I can manually take over the conversation myself. The goal was never mass spam. I wanted to see if lightweight automation combined with manual closing could still feel human enough to get real responses.

Yesterday was the first live run and it generated 4 positive replies. I also sold a version of the system to a client recently which was probably the bigger validation for me.

The hardest part so far has not been the automation itself. It has been making the personalization believable enough that people do not instantly assume it is botted outreach. Still improving deliverability, warm up behavior, follow up timing, and message quality.

Curious what outreach workflows are actually working for people here right now because LinkedIn automation feels way more fragile than it did even a year ago.

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u/chandlerbing006 — 20 hours ago

Built an AI LinkedIn DM Automation… but my content completely flopped. Need honest feedback.

I’m 21 and trying to break into the AI automation/content space. Recently I built a LinkedIn automation that writes and sends DMs in a way that feels more human and personalized instead of sounding like obvious AI spam. I spent a lot of time making it actually feel natural in conversations.

I turned the project into an Instagram reel because I thought the concept was strong, but it only ended up getting around 170 views. Now I’m genuinely trying to understand whether the problem is the content itself, the hook, the way I packaged it, or if I still don’t understand how creators in the AI automation niche actually grow.

I’d really appreciate advice from creators who’ve genuinely made progress in the AI automation space. What changed your content from getting ignored to actually getting traction? I can also send the reel or my Instagram page in DMs if anyone wants to see what I’m doing and give honest feedback.

reddit.com
u/chandlerbing006 — 4 days ago

Most people doing cold email are just blasting inboxes and hoping something sticks, and honestly, I was doing the same for a client in SAAS We were getting opens, but replies were dry and conversations went nowhere.

Then I noticed something interesting the few people who did reply weren’t ready to buy, they just wanted to figure out if we were legit.

So instead of pushing harder on email, I changed the approach. Whenever someone replied, I didn’t pitch them. I sent a LinkedIn connection request right away and followed it up with a short Loom video where I broke down something specific about their business.

No generic audits, no recycled lines just a quick 2–3 minute insight tailored to them. That simple shift made a big difference.

Conversations felt more natural, people actually remembered me, and calls didn’t feel like cold calls anymore. It stopped being “random email outreach” and started feeling like a real interaction. Still testing and refining, but this multi-channel approach is already working better than just sending more emails and hoping for replies.

Curious if anyone else here is doing something similar or seeing better results with a different approach?

reddit.com
u/chandlerbing006 — 24 days ago