Best AI Tools, Tips, And Prompts For Sales Prospecting

If your reps are still using AI like it’s 2023 (or not using it at all), they’re already behind. In our Sales Shot, I sat down with four sales pros and AI enthusiasts whose teams are actually using AI for sales prospecting, not just talking about it. We’re talking AI-enhanced targeting and prospect research, coaching bots, live conversation sentiment tracking, even inbound AI voice agents that are outperforming humans (yes, really – so, will AI take over sales jobs? That’s a topic for another blog!) 

Here’s what went down, and the best AI tools, tips, and prompts you’ll want to steal.

1. Smarter Targeting and Prospect Research

We kicked off with a game-changer: using AI to make sure you’re calling the right people. David Kreiger, SalesRoads, shared how his team uses Clay to qualify leads before reps ever pick up the phone. It pulls company data and uses AI to tell you if a prospect actually fits your ICP, saves hours of manual research, and gets your team focused on the right accounts.

John Buckley (from Sell Better’s Daily Sales Show) showed us Agent.ai, a no-code agent that scores a company for outbound fit with a single URL. He’s trained it on his ICP so it gives a quick thumbs-up or “hard pass.” No prompt writing needed.

Jax Gill (from Inspira Financial) took it even further. She trains ChatGPT to review a company’s website and her prospect’s LinkedIn profile, then find common ground to help her build rapport fast. She even gives it a list of her solutions and asks for possible pain points to reference in the convo. It’s like AI-powered pre-call prep, minus the rabbit holes.

Prompt ideas to steal:

• “Here’s my ICP. Here’s this company’s website. Is this a fit or not? Why?”
• “Compare my LinkedIn profile to [prospect’s name]’s. What do we have in common?”
• “Given this company and our services, what pain points can I lead with?”

2. Better AI Sales Prospecting Emails and Messaging

Let’s talk outbound emails. Doug Gibb’s team at Waste Management uses Conquer with GenAI email, which drafts emails based on past conversations and makes sure they don’t miss a promised follow-up. It pulls call and email history straight into Salesforce, so everything’s in one place.

David dropped this gem: if you write more than three emails a week, build a custom GPT. He’s trained his to match his tone and voice. Upload 50 of your best emails, and now your GPT can write in your style. It’s faster, but more importantly, it’s better.

WATCH: How to Build a Custom ChatGPT (shared by David)

James added Oliv to the mix. This tool sends him a cheat sheet before every call with company background, team bios, and even icebreakers. “Ask Chloe about her transition from radio hosting to content marketing” is way better than “Hope you’re well.”

One big reminder from everyone: AI-generated emails shouldn’t sound AI-generated. If your message is filled with fluff, jargon, or emojis in every line, it’s going straight to trash. Your prospects can smell it. Use AI to help, but still bring your brain.

Prompt ideas to steal:

• “Use my tone. Write a prospecting email for this company using the info from our last call.”
• “Summarize this LinkedIn profile in one sentence I can use as a cold email opener.”
• “Rewrite this message to sound more human, less like it came from a bot.”

3. Coaching, Confidence, and Call Reviews

AI isn’t just helping reps do the work. It’s helping them get better at it. David recommends using AI to coach yourself after calls. His reps drop their call transcripts into ChatGPT and ask for feedback. What could I have done better? What questions did I miss? It gives them a score and action steps to improve.

Jax uses AI before the call. She practices objections with ChatGPT in persona-mode. “Be a tough IT Director. Push back on cost.” It gives her reps a safe space to screw up and get better.

Doug’s team uses Conquer to transcribe and summarize every call. It flags sentiment dips, highlights next steps, and scores reps on their delivery. That all feeds into Ambition, where managers get a full coaching report before every one-on-one. And yes, even new managers can coach like pros because the system shows them exactly what to focus on.

We also shouted out Grw AI, a tool for roleplay call coaching. Reps can practice calls and get feedback based on real frameworks. It’s like flight simulator training for sellers.

I also shared how much I love using Fathom for call notes. I just click a button and boom, it gives me a clean sales summary with top pain points, current situation, and next steps. It’s fast, easy, and way more useful than generic transcripts. Use it for internal calls too to help you take notes and create to-dos.

Prompt ideas to steal:

• “You’re a skeptical IT Director. Let’s roleplay a cold call. Push back on price and security.”
• “Here’s my call transcript. What could I have done better? Give me a grade.”
• “Give me 3 coaching questions to reflect on after this call.”

4. Real-Time Insights and In-the-Moment Support

Sales moves fast. Reps don’t have time to dig through notes or scroll LinkedIn for the latest news. That’s where real-time insights come in.

James’s tip: Use LinkedIn Sales Navigator alerts. Ring the bell on your top prospects and accounts. You’ll get notified when they change jobs, get promoted, or post. Instant reason to reach out. That’s prospecting fuel your team is probably ignoring.

Doug’s team uses Ambition’s pre-read feature to prep for coaching. It pulls 90 days of call scores, KPIs, pipeline data, and even sentiment analysis so managers walk into meetings ready. Their AI-based pipeline insights show if deals are stuck, what changed, and where to focus.

David shared Trellus, a power dialer that lets reps pause mid-call to get AI-powered coaching suggestions. It’s like having a manager in your ear without the pressure.

Prompt ideas to steal:

• “Give me coaching advice based on this sales call recording.”
• “Summarize this opportunity pipeline for my one-on-one. What’s stuck and why?”
• “If my rep is below target on discovery, what should I review with them this week?”

5. AI for Inbound, Enablement, and Emotional Intelligence

You didn’t think AI was just for outbound, did you? David’s team is using Sela for inbound calls, and it’s outperforming human reps in tier-one qualification. The AI calls the lead, asks 2–3 qualifying questions, and routes the hot ones straight to an SDR. It’s efficient, repeatable, and for simple calls, often better than a live person.

James brought up Sybill, which reads facial expressions and body language during video calls. It sends post-call insights like, “Your buyer leaned back and widened their eyes when you said pricing.” That’s gold for follow-up and helps reps refine their messaging and emotional timing.

And of course, Doug’s team uses Microsoft Copilot, a company-approved, closed AI system integrated into their workflows. Their AI governance committee ensures compliance, which matters when your team is 50,000 strong.

Bonus tip from Jax: Use ChatGPT as your personal hype woman. “Give me a pre-call pep talk.” Or ask it to roast you. Either way, you’re showing up more confident.

Prompt ideas to steal:

• “Pretend you’re my mentor. Give me a 30-second pep talk before this big sales call.”
• “Roast me. What could I do better in my outbound pitch?”
• “Act like a buyer. Ask me 3 tough qualifying questions based on this service.”

READ: Confessions from a Late-Adopter: The Truth About AI for Revenue and Enablement Leaders

This session wasn’t fluff. These are real leaders, using real tools, getting real results. If your team is still scared of AI or waiting for some “perfect system,” you’re already behind.

The final takeaway?

“Use the time AI saves you to do the task better. Not faster. Better.”
– David Kreiger

TL;DR – Here are the best AI sales tools and how our panelists are using them:

• Agent.ai – James built an agent that scores companies instantly based on ICP fit, eliminating the need for prompt engineering
• Ambition – Doug uses it to prep managers for coaching with pre-read insights that include sentiment, pipeline data, and call scores
• ChatGPT – Jax shared how her team uses ChatGPT to simulate prospect objections and refine messaging before high-stakes calls; it’s like having a role-play coach on standby
• Clay – David uses Clay to pre-qualify leads and filter out non-ICP accounts, saving reps hours of manual research
• Conquer – Doug’s team uses it to auto-draft follow-ups based on call history and transcribe every conversation for coaching
• Fathom – We use Fathom here at Factor 8 to summarize sales calls and uncover real buyer pain points. Tip: Use it for both internal and external meetings to quickly extract key details, create to-do lists, and skip manual note-taking
• Grw AI – Lauren and Jax called it a flight simulator for sales; perfect for reps to practice and build confidence before high-stakes calls
• Microsoft Copilot – James noted that Copilot helps his team save time by summarizing long email threads and prepping for meetings straight from Outlook and Teams
• Oliv – James loves Oliv for the call prep emails, especially the personalized icebreakers like asking about career transitions
• Sybill – Doug mentioned using Sybill to flag buyer reactions mid-call, helping reps spot hesitation or interest and follow up more strategically
• Sela – David says Sela outperforms humans for tier-1 inbound lead qualification and is being used successfully in production
• Trellus – David mentioned reps can pause a call and get live coaching advice based on the persona or objection they’re handling