The Ultimate AI Toolkit for Sales & Enablement Leaders

AI is transforming how sales and enablement leaders work, but not every tool is worth your time. The real win comes from using AI to cut through busywork, speed up planning, and empower your team to perform at their best.

In this Sales Shot webinar, I sat down with Helen Fanucci, Rose Paik, Casey Calkins, and Dr. Richard Conde to cut through the noise and share the AI strategies that are actually working.

Here are the AI tools, prompts, and use cases worth stealing (and what you should skip).

Practical AI Use Cases That Are Saving Leaders Time

The biggest takeaway from our panel? AI is already drastically changing the game for sales and enablement leaders, and not in a distant future way. It’s helping them cut hours of work, make better decisions, and focus on the human parts of their job that matter most.

Helen shared a genius way to scale call reviews. Instead of sifting through hundreds of recordings, she uploads batches of transcripts into ChatGPT to surface competitor mentions, objection patterns, and whether reps are locking in next steps. It’s like a virtual coach doing the analysis for you, so you can spend time actually coaching.

Prompt to steal:
“Here are 20 discovery call transcripts. Create a table summarizing top objections, competitor mentions, and whether a next meeting was secured.”

Another smart move came from Rose, who built her own “clone” using Gemini. This persona enforces the company’s tone, writes in an active voice, and ensures content is clear and consistent across teams worldwide. The result is scalable sales training that actually sticks.

Prompt to steal:
“You are a sales enablement expert. Write onboarding instructions in an active voice, using customer-centric language at an 8th-grade reading level.”

AI can also help sales managers think faster and coach smarter. By feeding pipeline data into ChatGPT, Casey uses it to surface coaching priorities, the same insights an experienced leader would draw out, but in minutes instead of hours (grab Casey’s free AI toolkit for 6 AI prompts sales leaders need).

Prompt to steal:
“You are a frontline sales manager. Analyze this pipeline report and highlight three coaching priorities for my next one-on-one.”

Richard is taking a different angle by using AI to power better top-of-funnel strategies. He pairs Claude with Crystal Knows to understand buyer personality types, helping him craft outreach messages that feel personal, not spammy.

Prompt to steal:
“Here’s my target persona and their LinkedIn profile. Write a personalized outreach message that matches their communication style.”

These aren’t hypotheticals. They’re working right now. The leaders using AI this way aren’t just saving time; they’re leading smarter.

READ: Best AI Tools, Tips, And Prompts For Sales Prospecting

Smart Sales Coaching and Training with AI

AI isn’t here to replace coaching (or training), but our panel proved it can make coaching a whole lot more impactful. By letting AI handle the heavy lifting behind the scenes, leaders are freeing up more time to actually coach and connect with their teams.

One of the standout examples came from Helen, who built a custom Love Your Team bot to help leaders role-play tough performance conversations. Managers can pick a scenario (easy, medium, or hard), practice with the bot, and get scored on how they did. It’s a safe way to prepare for conversations most leaders dread.

Prompt to steal:
“You are an underperforming rep. Role-play a tough performance conversation with me and grade my responses.”

Rose is embedding AI directly into enablement the right way: skills first, AI second. Her team uses NotebookLM to create an interactive, searchable knowledge base from training content. Reps can ask it questions, generate FAQs, and even turn the material into podcasts in multiple languages, making learning easier to access and retain.

Prompt to steal:
“Based on this training content, create an FAQ for reps that focuses on what they need to do, not just what they need to know.”

GRW also came up as a powerful tool for role-play coaching, giving reps a safe environment to practice calls and get real-time feedback based on proven sales frameworks (like the Factor 8 COACHN Model).

Casey encourages leaders to train their GPT to think like them. By feeding it prompts that teach their leadership style and decision-making frameworks, managers create a digital “thinking partner” they can lean on for coaching plans and tough conversations.

Prompt to steal:
“Here is how I coach and communicate with my team. Learn my style and use it to draft coaching plans for these three reps.”

AI works best when it reinforces fundamentals instead of replacing them. Richard uses it for pattern recognition in sales scenarios, helping reps see what makes deals successful before they automate a thing.

Prompt to steal:
“Analyze these sales scenarios and identify patterns in what led to successful outcomes.”

The bottom line? AI makes coaching and training more scalable and personal, but it only works if you use it to strengthen (not sidestep) the human connection.

Table Stakes for Using AI Safely and Effectively

AI is only as good as the guardrails you set around it. The panel made it clear that using AI safely and effectively isn’t optional, it’s table stakes.

Privacy and data control came up first. Casey stressed that leaders must lock down privacy settings before letting teams run wild with new tools. Without clear guardrails, you risk exposing sensitive information. 

Prompt writing was another critical theme. Richard shared that the best outputs come from clear inputs: provide context, be specific, and always state your desired outcome. “Bad prompts get bad results,” he said. That’s why he often uses Claude to refine his prompts before sending them to other AI tools.

Helen showed how simple prompts can turn messy CRM data into clean, actionable summaries. Instead of spending hours in spreadsheets, she asks ChatGPT to create a table showing seller progress against objectives, giving her an instant snapshot of where to focus.

Rose brought it back to basics: start with the customer, not the tool. AI is there to help you serve buyers better, not to replace thoughtful strategy. When teams lead with AI instead of empathy, they risk losing the human connection that closes deals.

The message from all four leaders? The tools will not save you unless you teach them who you are, control what they see, and use them to make your work and your relationships stronger.

VIDEO: 8+ Critical Things Sales And Enablement Leaders Need To Know About AI

Time-Saving Hacks and Quick Wins

One of the best parts of this session was hearing the little hacks leaders use to save time without cutting corners. These weren’t big, shiny tech demos; they were practical shortcuts anyone can use.

NotebookLM was a fan favorite for Rose, who uses it like an interactive playbook. Instead of digging through static training docs, her reps can ask it “how do I” questions and instantly get answers. It can even generate FAQs or spin training material into podcast episodes in multiple languages, making learning accessible and easy to consume.

Casey shared how she teaches leaders to train ChatGPT to think like them. By feeding it prompts that define their leadership style, tone, and decision-making process, they turn it into a virtual assistant that knows how they would respond. This saves managers countless hours on repetitive tasks like drafting coaching plans or preparing for one-on-ones.

Richard uses Claude to sharpen his prompts before sending them to other tools. He calls it a “prompt coach” because it helps him ask better questions, which leads to better outputs everywhere else.

Helen keeps her workflow lean by asking AI to summarize CRM and call data into quick performance snapshots. Instead of pulling endless reports, she gets an at-a-glance view of what’s working and what’s not so she can spend her time coaching, not crunching numbers.

Fathom was another fan-favorite for turning meeting recordings into clear, actionable summaries, so leaders and reps can skip manual note-taking and focus on next steps.

For me, Oliv is the standout AI tool for saving time. I raved about it during the webinar, sharing how it delivers all my pre-call research straight to my inbox. No digging, no scrambling, just everything I need ready to go before the call. Oliv’s AI agents handle the admin grind behind meetings, from updating CRM fields to building follow-ups and proposals. For leaders, it automates forecasting and pipeline reviews, keeping everything accurate without the manual chase. 

These hacks may seem small, but together they save hours each week and keep leaders focused on what really moves the needle.

What AI Tools Are Worth It (And What to Skip)

When it comes to AI, there’s no shortage of shiny new tools, but only a handful are truly moving the needle for leaders. The panel didn’t hold back on sharing their favorites and the ones they’d leave behind.

For writing and content creation, Claude was a unanimous favorite. Both Richard and Rose rely on it for everything from drafting social content to formatting training materials. Richard even uses Claude to help craft better prompts, giving him cleaner outputs faster.

On the enablement side, Rose swears by her custom Gemini persona, the “Rose Clone,” to enforce tone and consistency in every piece of training content. She pairs it with NotebookLM to turn training materials into interactive, searchable resources that reps actually use.

For leaders coaching teams, Casey’s toolkit is full of must-haves. She loves using ChatGPT to analyze pipeline data, surface coaching priorities, and act as a sounding board for tough management decisions.

The session also spotlighted presentation tools worth bookmarking. Richard uses Napkin and Beautiful to quickly create clean, high-impact visuals, and pairs them with Canva for easy team collaboration. These tools make it faster to produce presentations that actually engage audiences without spending hours designing slides.

Not all tools got glowing reviews. Helen warned against relying on AI to write prospecting emails or LinkedIn outreach. Tools that blast generic messages do more harm than good. Her advice? Skip the automation here and pick up the phone. “Calling is back,” she reminded us. (We don’t think it ever went away 😉).

The panel also flagged a common mistake: blindly trusting AI outputs. Whether it’s using ChatGPT to summarize CRM data or leaning on any tool to draft content, accuracy isn’t guaranteed. Every AI output still needs a human eye before it goes out the door.

The takeaway? Tools like Claude, ChatGPT, Gemini, NotebookLM, and even quick-hit design tools like Napkin and Beautiful are worth the investment because they solve real problems. Tools that replace personal outreach or encourage copy-paste shortcuts? Skip them.

What’s Next for AI in Sales Enablement

The session wrapped up with a clear message: AI is here to stay, but how you use it determines whether it helps or hurts.

Helen reminded everyone not to let AI erode trust with customers or teams. Human connection still wins, and AI should support (not replace) that.

Richard sees the next wave already forming. AI agents acting like digital employees are coming fast, and they’ll change how leaders think about efficiency and staffing.

Casey urged leaders to focus on amplification. Use AI to make what you do best even better instead of trying to automate it all away.

And Rose left us with the simplest but most important reminder: no AI tool fixes bad fundamentals. Skills come first. Layer AI on top to scale and reinforce, not as a shortcut.

The future of sales and enablement isn’t human vs. machine. It’s human with machine, and leaders who embrace that balance are already pulling ahead. 

When I asked the panel if AI would replace sellers, the chat blew up with a resounding “NO.” That moment sparked an important reminder from Casey about how we should approach AI:

“AI will only replace humans if we let it. Use it to make yourself better,
not to take yourself out of the equation.”

The Best AI Sales & Enablement Tools

Here are the top AI tools from our panel and how they’re being used to save leaders time, improve coaching, and scale enablement:

• Beautiful – Creates polished, high-impact presentations without needing a designer.
• Canva – Makes it easy to design presentations and enablement content quickly with team collaboration.
• ChatGPT – Analyzes call transcripts, summarizes CRM data, role-plays tough conversations, and acts as a manager’s thinking partner.
• Claude – Used to draft content, refine prompts, and create cleaner outputs for training and social selling.
• ConnectAndSell – Speeds up live calling efforts and list enrichment for sellers.
• Crystal Knows – Helps tailor outreach messaging based on buyer personality profiles.
• Fathom – Automatically summarizes calls and meetings into actionable notes.
• Fireflies – Transcribes and summarizes meetings, saving time on manual note-taking.
• Gamma – Builds presentation slides in minutes with AI-generated layouts and content.
• Gemini – Powers custom personas like Rose’s “clone” for consistent content creation and translates training content across languages.
• Gong – Analyzes call recordings to surface buyer sentiment, track deal risks, and give managers data-driven coaching insights.
• GRW – Acts as a sales role-play simulator that provides real-time feedback based on proven coaching frameworks.
• Kronologic – An AI-powered scheduling assistant that automatically books meetings by recognizing when a lead is ready and sending a calendar invite from the rep’s email.
• Magi – Gives leaders access to multiple AI models like Claude and GPT in one interface, streamlining experimentation and prompt testing.
• MidJourney – Generates high-quality visuals and creative assets for content and enablement.
• Napkin – Quickly generates clean slide visuals and presentation graphics.
• NotebookLM – Turns training materials into interactive playbooks, searchable FAQs, and even multilingual podcasts.
• Oliv – Delivers pre-call cheat sheets with bios, company background, and personalized icebreakers to reps.
• Perplexity – Acts as an AI-powered research assistant for quick, accurate information retrieval during content creation or planning.
• RightBound – Uses natural language queries to create targeted prospect lists quickly, saving time on manual filtering.

Bonus: AI Tools Recommended by Attendees

Our audience came ready to share their own favorite tools. Here are a few worth exploring:

• Adobe Firefly – Leveraged for generative design and creative content projects (shared by Jim).
• Autobound – An AI-powered email writing tool that combines Claude and Gemini to craft smarter outbound messages (shared by Jason).
• Calendly – Now includes AI-powered note-taking, recording, and meeting summaries to streamline follow-ups (shared by Viveka).
• Copilot (Microsoft) – Used by several attendees to act as a virtual assistant, helping with meeting prep, drafting content, and automating repetitive tasks to boost productivity (shared by Jessica, Sandra, Angela, and Shawn).
• Custom Personas for ChatGPT – A resource with 300 pre-built persona templates to customize ChatGPT for specific roles or scenarios (shared by Demont).
• Otter – Helps transcribe meetings and create searchable notes; also praised for its robust subprocessors (shared by Demont).
• n8n – Used for building automation workflows that connect multiple tools and processes seamlessly (shared by Jason).
• ScreenApp – Captures and analyzes face-to-face meetings, providing outputs similar to Fathom for call insights (shared by Guy).
• Vengreso FlyEngage – Designed to boost LinkedIn engagement through personalized messaging and workflows (shared by Viveka).
• ZoomInfo – Used to create buying groups and surface intent signals to target prospects more effectively (shared by Glenn and Demont).