How to Automate Sales Prospecting with a Personal Touch

Just closed a major enterprise deal against a competitor who pitched at 1/3 of our price. Here's the inside scoop on how we transformed what started as a "chatbot search" into a complete GTM automation win: Here's what most vendors miss: Chatbots alone are just the tip of the iceberg. The real magic happens when you connect visitor intelligence to autonomous GTM actions. Reframing the Conversation : The prospect (a well-funded services company with 400+ employees) initially came to us looking for an AI chatbot and had done their homework. During our first demo, we showed them something dramatically different: Their current flow: Visitor chats with bot Lead gets logged Sales team manually follows up (maybe) Data sits in silos What we demonstrated live: AI chatbot engages visitor Platform instantly identifies the company AI agents then automatically: Create enriched company profiles Launch tailored outbound sequences Book meetings via voice/email Update their CRM in real-time Alert relevant teams in Slack/Teams The game changer? When we were able to demonstrate to their team the ways our AI agents were already acting autonomously based on chatbot interactions from other companies in their industry - booking meetings while competitors are still manually working over chat leads. Inbound Intelligence: Knows which companies are engaging (or not engaging) with the chatbot Analyze conversation patterns for intent signals Triggers targeted workflows by interaction type Routes high-value prospects to live sales teams Outbound Automation: AI agents autonomously prospect similar companies Creates targeted account lists by patterns of engagement with the chatbot Launches multichannel outreach (voice, email, LinkedIn) Syncs all activity back to their CRM The "Aha" Moment Instead of configuring a chatbot for them, we walked them through building a complete workflow in the demo: Key Takeaway: When you can show how a "simple chatbot" can become an autonomous revenue engine--price becomes irrelevant. The discussion shifts from "Do we really need another chat tool?" to "How soon can we put this complete GTM automation out there?"

When I read Tobias Lütke's memo yesterday, it made me reflect on how I personally use AI to run Outreach—and I thought it might be worth sharing with a wider audience. As many of you know, Outreach is an AI-powered sales execution platform, purpose-built to help revenue teams automate and optimize their workflows—from pipeline generation to deal closure. Here’s how I run Outreach using our own AI capabilities: 🔹 Forecasting: In our weekly forecast call, I benchmark our rollups against what Outreach AI predicts. It processes everything—deal updates, customer interactions, notes, and conversation intelligence—providing deep insights at a scale no human could match. 🔹 Deal Execution: I use our Deal AI Assist to stay close to mission-critical opportunities. It tells me which deals are on track and where I can jump in to support the team. 🔹 Account Monitoring: I track our top accounts daily with Account AI Assist, which flags churn or contraction risks based on conversation signals and behavioral data. 🔹 Seller Coaching: I rely on Kaia's (our Conversation Intelligence AI) real-time coaching to help our reps improve on the fly—whether it’s competitive differentiation, pricing strategies, or structuring complex deals. 🔹 Customer Success: Our Reflexive AI alerts CSMs when product usage and adoption drop, so we can proactively re-engage accounts before it's too late. 🔹 Prospecting: Our AI Prospecting Agent continuously runs in the background—scanning signals, evaluating fit, and reaching out autonomously when the time is right. It personalizes content across email, LinkedIn, and call scripts, saving our team an estimated 10x in effort. All of this—powered by the Outreach platform—is how I stay close to the business while letting AI do the heavy lifting. If you’re curious about how you can run your own company with Outreach AI, drop me a message. I’d love to show you. #AI #SalesExecution #Leadership #OutreachAI #FutureOfWork #SalesTech

How I built a LinkedIn lead machine that runs on autopilot (And how you can too): Most people overcomplicate LinkedIn lead generation. They: • Post constantly • Pray for inbound leads • Send cold DMs that get ignored Some try running ads too. But without a system in place, they just end up burning cash. I built a system that brings in 20-25 leads per month for my own business. And for my coach clients? They’re getting 60+ leads per month and filling their calendars with booked calls. The best part: Once it’s set up, it runs on autopilot. Here’s exactly how it works: Step 1: Start with LinkedIn Ads Forget boosting posts—that’s a waste of money. Instead, use Lead Gen Ads to capture emails from high-intent prospects without sending them to an external landing page. Step 2: Automate LinkedIn nurturing with Expandi Once someone opts in, they’re automatically added to Expandi, which handles LinkedIn outreach. First, they get a personalized connection request (automated, but looks manual). Once they accept, they go through a 5-message nurture sequence inside LinkedIn DMs. This warms them up and guides them toward booking a call. Step 3: Add email follow-ups At the same time, they’re placed into an email nurture sequence. This reinforces credibility with: • Case studies • Testimonials • Industry insights — keeping them engaged beyond LinkedIn. Step 4: Retarget like a pro Most leads won’t book a call immediately. That’s normal. So, we retarget them with ads that keep them engaged— Whether they’ve: • Watched a video • Interacted with a post • Clicked on an ad before Step 5: Use "HighLevel" to track & convert leads Leads don’t mean much if they fall through the cracks. That’s why everything flows into HighLevel (CRM). Every lead is tracked, categorized, and followed up with at the right time. Warm inbound leads get automated responses so no opportunity is missed. Everything is centralized, making it easy to manage conversations across LinkedIn, email, and inbound inquiries. Step 6: Optimize & scale The beauty of this system? It gets smarter over time. We test different messages, refine ad copy, and double down on what works. This is exactly how I generate my own leads. And I build the same system for my clients. If you’re a: • Coach • Consultant • Service provider ... tired of chasing leads and want a LinkedIn system that does the work for you, let’s talk. DM me the word "ADS" and let's see if we're a good fit. Thanks for reading. Enjoyed this? Follow Connor Bell for more.

How I create highly targeted outbound lists here at Sell Better (LIVE EXAMPLE) For those of you who don't know, I recently took a bigger role there to help build the outbound motion. Our TAM isn't huge. And we have a select list of accounts we want to go after. I'm using Common Room to pull all relevant signals from contacts at those accounts into one place. That way I'm always focused on the warmest leads (and have all the relevant info to reach out to them). Here's how I do it step-by-step (& how you can too): Step 1: Import my target accounts and/or ICP into Common Room Step 2: Connect all sources where my ICP is active In my case, the #1 source is LinkedIn. So Common Room lets me track who, in my ICP, is engaging with our content. Step 3: Filter the list even further with additional signals Common Room has a TON of built-in signals (tech stack, job changes, social activity, etc.) So I can narrow the list even further (and make my messaging even more relevant) by adding them. Step 4: Automatically push those to a sequence to begin prospecting This is my favorite part. If you set up Common Room the right way, you don't have to worry about finding new leads to prospect each day. You can set it up on auto pilot so that the warmest leads are loaded into a sequence for you each day. #sales #outbound