Looking For Guidance on Selling AI Chatbots✌️

Hey everyone🙋‍♂️

I’m planning to seriously start building and selling AI chatbots to businesses (lead qualification, booking, customer support, follow-ups etc.), and I wanted to tap into the experience in this group before I go all-in.

Right now, I’m trying to figure out the smartest way to approach this, so I’d really appreciate any advice on a few things:

1️⃣ Lead generation

What’s actually worked best for you when getting your first clients?

Cold outreach, warm intros, ads, local businesses, platforms like Upwork, or something else entirely?

2️⃣ Converting clients efficiently

Once you’ve got a lead interested in AI/chatbots, what helped you close them?

Demos, free trials, case studies, guarantees, pricing structure, etc. — what moved the needle for you?

3️⃣ Social media vs direct outreach

Do you think it’s worth building a personal brand / posting on social media (TikTok, Twitter, LinkedIn) to attract clients long-term, or is it better to focus purely on direct sales at the beginning?

4️⃣ Challenges & wins

For anyone already doing this:

What were the biggest challenges you ran into early on?
What were your first wins that gave you confidence this could work?

I’m fully aware this space is noisy right now, which is why I want to learn from people who’ve already tested things in the real world rather than guessing.

Appreciate any insights — even short replies help a lot 🙏

Thanks in advance.

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