The 1:1 System That Builds Top Performers [Webinar]
The 1:1 System That Builds Top Performers
[Video Recording]
Coaching (COACHN℠)
How to Use AI to Write a Better Sales Intro
Most sales call introductions fail because they sound exactly like sales call introductions.
You know the one. “Hi, my name is Lauren and I’m calling from XYZ Company, we’re the leading provider of blah blah blah…” The prospect checked out three seconds in. They’re scanning emails, mentally planning dinner, and looking for the fastest way off the phone.
That’s not a conversation. That’s a pitch disguised as a greeting. And it’s killing your pipeline.
After 20+ years of training Fortune 500 sales teams, I can tell you this: the reps who book the most meetings aren’t the ones with the best pitch. They’re the ones who get the prospect talking before they even realize they’ve taken a sales call.
Here’s how to use AI to craft a sales intro that’ll engage your prospects and get them talking.
First, Let’s Reframe What Selling Actually Is
Nobody wants to feel “salesy.” That word makes people cringe because of the stereotype: pushy, aggressive, slimy. A HubSpot poll found that only 3% of people trust salespeople. (Still just above politicians, so there’s that.)
But here’s what most people forget. Buying is fun. Think about the last thing you bought that made you genuinely happy. If buying feels great, then helping people get there should feel great too.
Selling is connecting one on one with another human to help them accomplish their goals. That’s the real definition. When you reach out to a prospect who’s stuck between “maybe” and “do nothing,” you’re not being pushy. You’re helping them get past the analysis paralysis. You’re making it easier to solve their problem.
Less than 10% of buyers will close themselves without any human help. That’s a lot of money left on the table because nobody picked up the phone.
WATCH: AI Sales Intros That Capture Leads in 30 Seconds
Why Phone Prospecting Still Matters
I know. You’d rather just email or DM people on LinkedIn. It’s more comfortable. It feels less intrusive.
It’s also three times less effective.
The noise in inboxes is deafening. Even with AI-personalized outreach, written messages alone don’t cut it anymore. The most efficient sales prospecting strategy uses all channels: social, email, and phone. But if you want the biggest results, you have to call.
Here’s the math. If you carve out one hour a day to reach out to 20 leads by phone, you’ll talk to one or two of them. Do that five days a week and you’ll touch 100 leads, have 5 to 10 real conversations, and rack up more than 200 first-base conversations in a year.
How many do you have now?
Research from CEB shows that 53% of the time, buyers will choose the seller who was first to add value. Not just first to reach out. First to actually be useful. That’s the key. Being first without adding value doesn’t work. Volume plus value does.
And here’s the thing most reps don’t realize: it takes 8 to 12 attempts to actually reach a decision maker. But nearly 50% of sellers give up after just one call. Less than 2% will make more than six. If you persist, you will be the first one to have a real conversation with that buyer. That’s a massive competitive advantage.
The Biggest Cold Call Introduction Mistakes Reps Make
Before we build a better intro, let’s talk about what’s broken. And let’s be clear: don’t be like every other rep who shows up and throws up. You know the ones.
Pickup and Pitch. “Hey, my name is Lauren and we’re the leading provider of this and that and I can da da da…” They just pitch. It’s pickup and pitch, and it gives sales a bad name. They didn’t pick up the phone to get pitched at. They picked up because they thought it was their kid’s school calling.
“Are you the person in charge of…?” I’ll lie to you to get out of having a sales call. This one screams sales call so loud that your prospect will say anything to end the conversation.
The Value Prop Intro. “Hi, this is Lauren. I’m calling with #GirlsClub, and we’re the premier community for women in revenue to get promoted faster.” Ugh. Shut up. I did not pick up the phone to hear your positioning statement. This is another very popular bad intro.
“Just calling to introduce myself.” Your mom might care. Nobody else does.
“Just calling to touch base.” Drum roll please. This is the most often used intro line in sales, and it’s horrible. Don’t touch my base. Don’t touch anything.
All of these fail for the same reason. They make the call about you. Your company. Your product. Your agenda. The prospect doesn’t care about any of that yet.
DOWNLOAD: 20 Value-Add Reasons to Call Your Customers
What a SWIIFT Sales Call Introduction Actually Is
SWIIFT stands for “So, What’s In It For Them”. It’s a call introduction framework designed to capture attention, get the prospect talking, and start a conversation before they realize they’ve taken a sales call.
A good SWIIFT intro does three things:
- It’s under 10 seconds
- It answers three questions: Who are you? What do you want? Why should I care?
- It ends with questions that get the decision maker talking fast
The goal of your introduction is not to pitch. It’s not to gain credibility. It’s not to check off items on your call sheet. The goal is to get them talking. Because the second they start answering questions, they stop doing email. They stop multitasking. Now you’re in a conversation, and you’re on first base.
Here’s the formula:
- Their name (loud enough to be a pattern interrupt)
- Your name and company (abbreviated, fast, they’ll ask again later)
- One SWIIFT ear perk (a single value that makes them look up)
- 1 to 3 closed SWIIFT questions (easy to answer, gets them talking)
That’s it. No pitch. No product description. No “let me tell you about our award-winning platform.” Just enough to start a conversation.
The 6 Value Levers That Perk Up Attention (Plus One Bonus)
The ear perk is the secret sauce of the SWIIFT intro. It’s one short sentence that hits a value your prospect actually cares about. We call them the SWIIFT Six:
- Time – “I’m calling to save you some time on…” Everyone’s busy. Time savings always land.
- Money – “I’m calling to help you kick up the ROI on…” More revenue, less cost, better margins.
- Ease – “I’m calling to make this a lot easier for you.” This is the hot button for working parents and overwhelmed managers.
- Reputation – “I’m calling to make sure you’re the hero on this.” Looking good, being recognized, being the one who brought in the solution.
- Power – “I’m calling to help you get control over…” Control and influence motivate more people than you’d think.
- Risk – “I’m calling to pull all the risk out of…” Insurance, compliance, protection. If your product reduces exposure, lead with it.
And the bonus lever: a name. When someone hears “Mark in Legal asked me to give you a call,” they instantly give you credibility. Levers like referrals, mutual connections, or internal names are the most powerful ear perks you can use.
Pick one. Just one. Your instinct will be to cram your entire value prop into this sentence. Resist. When I teach this in workshops and ask people what they remember from each other’s intros, they always say the same thing: one word. “Risk.” “Easier.” “ROI.” That’s all they heard. Don’t overcomplicate it.
You can use AI to help pick the right lever. Ask ChatGPT or your AI tool of choice: “Which of these six business values would a VP of Sales care most about?” or “What does a working mom in operations value most?” Then build your ear perk around the answer.
Why Closed Questions Beat Open Questions at the Start of a Cold Call
Here’s where I’m going to go against what every sales training has ever taught you.
Most sales trainers say always ask open-ended questions. And in discovery calls, that’s great. But on a cold call introduction, open questions are a disaster.
Think about it. Your prospect wasn’t expecting your call. They’re busy. They accidentally picked up. And now a stranger is asking, “What’s keeping you up at night when it comes to hiring?” Their brain tries to process it, can’t come up with an answer fast enough, recognizes you’re a salesperson, and decides to get rid of you.
Instead, use closed questions. Yes or no. A number. One or two words.
There’s a scientific phenomenon called instinctive elaboration. When someone asks you a question, your brain stops what it’s doing and hunts for the answer whether you want it to or not. If I ask, “How old are you?” a number popped into your head just now. That means it’s halfway out of your mouth.
Closed questions exploit this. They’re fast, they’re easy, and they get the prospect talking before they’ve had time to put up a wall.
Compare these two:
Option A: “You’ve got over 50 sellers on your team these days, right?”
Option B: “How have you and your team managed to attack virtual onboarding ramp times given that they’re getting longer at most companies I work with now that work is remote?”
You stopped listening in the middle of B. So did your prospect. A is the winner, every time.
How to Tell If Your AI-Written Sales Intro Actually Works
Let’s put it all together. Here are two complete SWIIFT intros side by side. One works. One doesn’t. If you’re using AI to generate intros, this is how you evaluate what it gives you.
Option A: “LB here with Factor 8. I’m calling to see if I can help your team hit quota sooner. Are you primarily B2B there? Do you outbound or inbound? How many sellers under you?”
Option B: “LB here with Factor 8. We’re the leading provider of virtual sales skills for inside sales teams. We work with companies like yours to shorten new hire ramp. Is that interesting to you?”
A is the winner. Hands down.
A leads with one value (hitting quota sooner), then immediately gets the prospect talking with three fast, closed questions. B leads with a company pitch and ends with a question that’s basically asking the prospect to reject you.
“Is that interesting to you?” is an invitation to say no. “How many sellers under you?” is an invitation to have a conversation.
Now here’s what it looks like when you add a lever:
“Mark? LB here with Factor 8. Your VP of Sales asked me to give you a call and I promised him I would. Have you worked with David for a while now? Are you running inside sales or field sales for him? How many reps on your team?”
That’s three easy questions. By the time they answer the second one, you’re in a conversation and they’ve forgotten they accidentally picked up a sales call. That’s first base.
How to Use AI to Draft Sales Intros Without Sounding Like a Bot
AI is a fantastic tool for generating SWIIFT intros. But it’s a starting point, not the finish line.
Here’s how to use it well. Feed your AI tool these inputs:
- Who you’re selling to (title, industry, persona)
- What your product does in one sentence
- Which of the SWIIFT Six values resonates most with your buyer
- Your name and company name (abbreviated)
Then ask it to generate a SWIIFT intro under 10 seconds with one value-based ear perk and two to three closed questions.
DOWNLOAD: The SWIIFT℠ Intro AI Prompt
What you’ll get back will be close. But you’ll need to do two things: cut it shorter (AI loves to be wordy) and make it sound like you. Read it out loud. If it sounds like a brochure, rewrite it. If it sounds like something you’d say to a friend’s colleague at a barbecue, you’re golden.
The best reps use AI to generate five or six variations, pick the best one, and then practice it until it feels natural. That’s the move.
Grade Your Intro Before You Dial
Before you pick up the phone, run your SWIIFT intro through this checklist:
- Is it under 10 seconds?
- Does it answer who you are, what you want, and why they should care?
- Does it use a single value (not three stacked together)?
- Does it end with 1 to 3 closed, easy-to-answer questions?
- Would it perk your ear if you heard it?
- Would you actually answer those questions?
If you can check every box, you’re ready. If not, shorten it, sharpen the value, and simplify the questions.
Get the Conversation, Not the Pitch
You can’t close more deals until you talk to more people. You can’t talk to more people if your intro sounds like every other sales call they’ve gotten this week.
Stop leading with your company name, your product features, or your credentials. Start leading with what’s in it for them. Be SWIIFT. Keep it under 10 seconds. Get them talking. And remember: the goal of the intro isn’t to sell anything. It’s to start a conversation.
Because nobody ever bought anything during a sales call introduction. But plenty of deals started with one.
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5+ Sales Coaching Tactics Top Managers Use Today (and How AI Helps) [Webinar]
THIS WEBINAR IS SPONSORED BY:
Gong is the #1 AI Operating System for revenue teams. Move faster, coach smarter, and hit targets with fewer surprises. Gong cuts down manual work, captures real buyer signals, and guides reps to action so more deals close and more sellers hit quota.
Check out their guide, “Sales playbook for frontline managers: 4 coaching best practices“ to unlock your team’s potential.
Top Sales Trends and How to Thrive in an AI-Driven World
Sales is changing fast. AI is accelerating everything, buyers are harder to impress, and mediocre selling is getting exposed.
That’s the bad news.
The good news is also simple: the teams that win are going to be the ones who get clear, get current, and double down on human skills that actually move deals forward.
Here are the trends I’m seeing, and the practical moves to make right now if you want a strong year.
1. Get crystal clear on your goal (because nobody is coming to save you)
We’re living in the noisiest time in history. Tools. Tactics. Hot takes. EVERYONE SHOUTING (😉).
If you wait for clarity, you’ll be waiting forever.
Set your own clarity:
- What is the actual outcome you want this year?
- What do you want to be known for?
- What do you want your next role to be?
- What’s the one skill you’re unwilling to be mediocre at?
Then act like you mean it. Put it on your calendar. Build your plan around it. Stop drifting.
2. AI is not replacing you, but it is replacing “entry-level effort”
AI will absolutely wipe out a lot of low-level tasks. Anything that looks like copying, pasting, summarizing, basic research, first drafts, list building, and “good enough” outreach is getting automated fast.
So here’s the play:
- Use AI to get efficient
- Use humans to get effective
If you’re a rep, AI can help you research, organize, and prep.
If you’re a frontline manager, AI can help you spot trends, clean up pipeline signals, and prep for better coaching conversations.
If you’re a sales or revenue leader, AI can help you scale what’s working, identify risk earlier, and make better growth decisions without losing visibility into the human side of performance.
If you’re in enablement, AI can help you reinforce consistency in skills and training, but it should not define what “good” looks like.
READ: The Ultimate AI Toolkit for Sales & Enablement Leaders
3.The human side of sales just became the differentiator
As marketing and automation go further “digital,” the moment a buyer finally talks to a human matters more than ever.
Which means sales has to feel less like a pitch and more like a helpful consultation.
If your selling is still built on:
- Generic sequences
- Shallow discovery
- Long demos that say everything and solve nothing
- Follow-up that’s basically “just checking in”
You’re going to feel the shift.
The bar is rising. Thank God.
4. Prospecting is getting harder and more important at the same time
AI has made outbound louder. Not better. Louder.
So prospecting wins this year when it’s:
- More personal
- More relevant
- More direct
- Less “spray and pray”
Practical upgrades:
- Personalize to the problem, not the person. “Saw you went to Ohio State” is not value.
- Lead with a point of view. “Here’s what we’re seeing in companies like yours.”
- Have a real reason to reach out. A trigger. A change. A risk. A missed opportunity.
- Keep it short. Make it easy to respond.
And yes, pick up the phone. Calls are weirdly becoming a differentiator again because fewer people are doing them at all, or well.
READ: Best AI Tools, Tips, And Prompts For Sales Prospecting
5. Discovery and conversation skills are the new conversion rate
Buyers do not want to be pitched at. They want to feel understood quickly.
Your edge is better discovery:
- Ask sharper questions
- Listen harder
- Connect pain to impact
- Create clarity, not confusion
A simple standard: if the buyer can’t clearly explain the problem and the stakes after talking to you, your discovery wasn’t discovery. It was a tour.
READ: 4 Steps to Asking Better Sales Discovery Call Questions
6. Demos are changing: shorter, tighter, more customized
The era of the 45-minute “power demo” is fading.
Teams are moving toward:
- Micro-demos
- Self-serve exploration
- “Show me exactly what I asked for” experiences
- Recordings that help buyers sell internally
If your demo is still a feature parade, you’re doing product theater, not selling.
Make demos:
- Smaller
- More specific
- Tied to their use case and decision criteria
7. Call bridging is one of the fastest ways to prevent ghosting
Ghosting isn’t new. Buyers disappearing mid-deal is basically a sport now.
One of the simplest skills that helps is call bridging: setting up the next step while you still have them, with clarity and agreement, so follow-up isn’t chasing.
Quick example language:
- “Before we hang up, what needs to be true for you to feel good about moving forward?”
- “If we’re aligned, what’s the next best step on your side and mine?”
- “Let’s lock the next conversation now so we don’t lose momentum.”
It’s not pushy. It’s professional.
READ: Call Bridging 101: Paving the Way for a Follow-up Sales Call
8. Pipeline and forecasting are finally getting help (but your CRM can’t be garbage)
More teams are leaning on AI for forecasting. That’s a win.
But AI can’t save you from messy inputs.
If your CRM stages are fuzzy and everyone has their own definition of “qualified,” you’ll still get bad forecasts. They’ll just arrive faster.
Team move to make:
- Define clear stage gates
- Decide what must be true to move forward
- Build the habit of updating reality, not optimism
9. The skill plan matters as much as the tech plan
Most organizations spend way more on tools than training.
Tools are coming. Skills are what will separate teams.
If you’re a leader or enablement:
- Budget time and money for skill development
- Build an ongoing cadence so training isn’t a one-time event
- Make practice normal, not rare
- Don’t rely on video alone and call it “training”
People don’t change from watching. They change from doing.
READ: The Secret to Scaling Sales Team Revenue: Your Managers
Role-based game plan (so you actually use this)
If you’re a rep
Put these blocks on your calendar weekly:
- Research + personalization time
- Call time
- Follow-up time
- Skill practice time (one skill, not ten)
If you’re a manager
Protect your calendar or you’ll burn out:
- Weekly group pipeline time (group, not endless 1:1 firefighting)
- Weekly coaching block (deeper coaching, not drive-by feedback)
- Monthly strategy and career development conversations
- Quality checks (quality over quantity)
If you’re a sales or revenue leader
Scale without losing control:
- Weekly visibility into pipeline health and risk, not just totals
- Clear definitions for stages, forecasting, and “what good looks like”
- Regular inspection of skills, not just numbers
- Investment in both systems and people, not one or the other
If you’re in enablement
Speed is the name of the game:
- Build the muscle of a training cadence first
- Then swap topics in as the world changes
- Keep humans defining what “good” looks like
- Use AI tools to spot patterns, not replace coaching
READ: 8 Sales Enablement Best Practices to Partner with Revenue Leaders
This year is going to reward the people who stay current, build real skill, and show up as humans.
Use AI to get faster. Use your people to get better.
And please, for the love of all things, don’t let a robot set the standard for your customer conversations.
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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).
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How Sales & Enablement Leaders Are (and are NOT) Using AI to Work Smarter, Not Harder [Webinar]
How Sales & Enablement Leaders Are (and are NOT) Using AI to Work Smarter, Not Harder
[Video Recording]
Meet the Speakers
Lauren Bailey
Founder
Factor 8 & #GirlsClub
Lauren Bailey, known to many as “LB”, is a sales leader, enablement leader, and entrepreneur and founder of 3 successful brands: Factor 8, providing front-line job training for inside sellers and managers, The Sales Bar, a subscription-based virtual sales training platform, and #GirlsClub, a community and development program helping more women earn leadership positions in sales.
Rose Paik leads Global Sales Development Enablement at Docusign, where she’s transforming how teams learn and perform through innovative AI solutions. Rose focused on AI-enabled adaptive learning while earning her Master of Science at Johns Hopkins School of Education. She’s passionate about using AI to unlock human potential and make enablement more impactful, not just more efficient. When she’s not building the future of sales enablement, you’ll find her experimenting with new AI tools and sharing practical insights with the enablement community.
Helen Fanucci
Sales Performance Expert,
Speaker, Author
Helen Fanucci is an accomplished sales performance expert, team builder, business leader, venture investor, and trusted advisor to technology growth companies, with a track record of leading high-performing sales teams at IBM, Apple, Sun Microsystems, and Microsoft. Helen currently leads a private sales performance practice focused on empowering sales leaders and their teams to deliver predictable growth. Helen is the author of the best-selling book, Love Your Team, A Survival Guide for Sales Managers in a Hybrid World.
Helen serves on the Board of Directors of Legacy Executive Club, a membership organization focused on uplifting careers and enriching lives, as well serving on the Board of Directors at the 5th Avenue Theatre, Seattle’s leading musical theater.
Dr. Richard Conde
Assistant Professor
University of Houston-Downtown
Richard Conde is an Assistant Professor at the University of Houston-Downtown, responsible for teaching sales MBA seminars, as well as digital and international marketing courses. As the lone full-time academic inside sales researcher, Richard is recognized as an expert in inside sales performance, leadership, and operations. His research has been published in the European Journal of Marketing, the Journal of Business and Industrial Marketing, the Journal of Marketing Theory and Practice, the Journal of Marketing Intelligence & Planning, and the International Journal of Higher Education.
Before transitioning to academia and consulting, Richard led mid- to large-scale inside sales operations, managing up to 400 inside sales agents and leaders. During his tenure as a sales executive, Richard was recognized for managing a $400 million book of business and increasing sales revenue from approximately $65 million to over $100 million in three years, while employing fewer inside sales agents. He also improved employee satisfaction from 3.6 to 4.6, based on the Gallup Survey.
Casey Calkins
Founder, Executive Coach
C2it Partners
Casey Calkins is the founder of C2it Partners, an executive and sales leadership coaching firm that helps new and emerging sales leaders build high-performing teams — without burning anyone out in the process.
A SaaS sales leader with 15+ years of experience at companies like Salesforce, Casey led high-performing teams through mergers, acquisitions, and leadership transitions, while also serving as a culture builder for a rapidly growing new office location. She launched ERGs, developed enablement frameworks based on emerging team trends, and turned top-performing teams into talent pipelines — with an average of 40% of her reps promoted annually into senior AE and leadership roles.
Today, as a Professional Certified Coach (PCC, ICF) and Certified Executive Coach (CEC), Casey helps leaders apply practical frameworks, emotional intelligence, and systems thinking to drive results, motivate teams, and lead with confidence. She is passionate about making AI accessible for busy leaders, showing them how to use it as a tool to work smarter — not harder — in coaching, planning, and communication.
4 Sales Manager Types Explained: Strengths, Skill Gaps, and Growth Tips
Most sales managers never got formal training. They were great reps, promoted for crushing quota, and then… handed a team.
Sound familiar?
Managing people requires a whole new set of skills. And when you’re juggling forecasts, pipeline reviews, and never-ending fire drills all before lunch, it’s easy to default to what you think good management looks like.
That’s why I created the Sales Manager Quiz. It’ll help you identify your natural leadership style and see what’s working and where you can level up.
In this deep dive, we’re breaking down the four manager types (Powerhouse, Cheerleader, Quarterback, and BFF) and…
- What each type nails
- Where they struggle
- And exactly how to level up
This isn’t a personality quiz just for fun (though it is fun). It’s a growth tool to help you lead more effectively, feel more in control, and build the kind of team that actually hits their number.
The Powerhouse Manager
You’re the engine of the team. Powerhouses get stuff done, no excuses, no delays, no loose ends. Your standards are sky-high, your work ethic is unmatched, and your team probably describes you as intense, but fair. You’re the person people trust when they need results fast.
But here’s the tradeoff: That pressure you thrive under? It can overwhelm your team. When everything is urgent and nothing falls through the cracks, reps can struggle to keep up or feel like they’re always letting you down. You may find yourself stepping in to fix things, juggling too much, or skipping coaching because it feels slower than just doing it yourself. Sound familiar?
If you’re a Powerhouse, your next level of leadership isn’t about doing more, it’s about doing less and leading smarter.
Traits:
High achiever, results driver, flawless executer, pressure lover, chronic improver, priority juggler
Strengths:
- Creates a high-performance culture
- Work gets done on time (and done right)
- Team focuses on the right things
- Solves problems quickly
- Leads by example
- Pushes team to deliver results
Areas for Growth:
- Risks burnout — both for self and team
- Micromanages instead of developing independence
- Prioritizes task reviews over real coaching
- May miss signs of team fatigue or lack of collaboration
How to Level Up:
- Block time for dedicated skill coaching
- Use a standard coaching form: 3 wins + 1 area to improve
- Set one clear priority at a time
- Assign ownership to reps (even if you’d do it faster)
- Add team-led training sessions to build collaboration
Resources:
- Download: The Eisenhower Matrix – Use this worksheet to prioritize what actually moves the needle and stop wasting time on low-impact tasks that drain your day.
- Course to Take: Own Your Day – The go-to course for managing priorities, time, and team expectations without burning out.
The Cheerleader Manager
You’re the hype squad, heart, and hope of your team. Cheerleaders are natural motivators who lead with positivity, praise, and a deep belief in their people. Your reps feel seen, supported, and genuinely like coming to work. You’re the one reminding them they’ve got this, because they usually do.
But high morale doesn’t always equal high performance. If you’re not careful, you might avoid giving hard feedback, hesitate to push underperformers, or focus so much on celebrating strengths that you miss the growing skill gaps.
Being a Cheerleader means balancing the pep with a plan. Confidence is the fuel, but your reps still need a clear destination and a map to get there.
Traits:
Confidence builder, esteem booster, strength finder, encourager, positivity spreader, inspirer of self-directed improvement
Strengths:
- Builds confident, high-performing teams
- Creates a safe, engaging team culture
- Reinforces wins to accelerate growth
- Boosts rep loyalty and retention
Areas for Growth:
- Hesitant to give tough feedback
- May avoid holding reps accountable
- Over-focuses on strengths, under-focuses on gaps
- Team may not be improving skills or results
- Lacks systems to track progress
- Risks getting blindsided on forecasts
How to Level Up:
- Set clear, measurable skill and results goals
- Use a balanced meeting framework (coaching + accountability)
- Start peer mentoring to scale support
- Schedule recurring team trainings to improve skills (not just confidence)
Resources:
- Download: The COACHN Model – Use this framework to run more effective 1:1s, coaching sessions, and performance conversations that actually drive action.
- Course to Take: Having Difficult Conversations – helps managers deliver honest feedback with empathy and clarity.
The Quarterback Manager
You’ve been in the trenches. You’ve carried the bag. You know exactly what it takes to win a deal, because you’ve done it a hundred times. As a Quarterback, your team relies on you for play-by-play guidance, deal-saving advice, and that one perfect story that closes the deal. You’re sharp, strategic, and always ready to jump in and move things forward.
But here’s the catch: if you’re always calling the plays, your reps never learn to run them. That creates a team of highs and lows, some stars, some stragglers, and a lot of dependence. You may find yourself rescuing deals instead of coaching skills, or relying more on stories than questions.
To level up, it’s time to trade the helmet for the headset. Coach the rep, not the deal.
Traits:
Leader of deals, experienced pro, knows how to win, storyteller, answer man, saver of deals
Strengths:
- Deep sales expertise and sharp instincts
- Knows how to map the path to success
- Offers tactical, deal-specific advice
- Leads confidently from experience
- Earns quick trust from the team
Areas for Growth:
- Inconsistent team performance (highs and lows)
- Focuses too much on deals, not enough on rep development
- Struggles to let reps fail and learn
- Doesn’t block enough time for skill coaching
- Leans on telling stories instead of asking questions
- May unintentionally build a team of “mini-me” clones
How to Level Up:
- Run win-loss sessions (game tape style) to break down deals
- Take a manager coaching course to shift focus to skill-building
- Share personal failures to normalize mistakes
- Establish a regular cadence of 1:1s, team meetings, and reviews
- Appoint peer experts to foster independence and collaboration
Resources:
- Download: Tasks to Start vs. Stop Doing – Use this guide to shift out of “super rep” mode by focusing on high-impact leadership tasks and leaving the old rep responsibilities behind.
- Course to Take: The COACHN℠ Model – helps you coach reps more consistently and shift from fixer to developer.
The BFF Manager
You’re the safe space. The one your reps vent to. You know their pets’ names, their partner’s promotion status, and who’s on the verge of burnout (because they told you, not their therapist). As a BFF manager, your superpower is trust. Your team feels supported, understood, and motivated—and in today’s world, that’s no small thing.
But emotional intelligence isn’t a substitute for leadership. When you’re too close to your team, it gets harder to hold the line. Performance conversations get postponed. Boundaries blur. And the reps you care most about? They may end up stuck, because no one’s pushing them to grow.
Being a great manager isn’t about being liked. It’s about being respected and effective. You already have the heart. Now it’s time to build the structure.
Traits:
Empathetic, emotionally attuned, deeply connected, personal motivator, team nurturer
Strengths:
- Builds strong morale through personal connection
- Creates psychological safety and trust
- Reads emotional cues and team dynamics well
- Motivates with recognition and empathy
- Fosters collaboration and peer support
Areas for Growth:
- Too patient with underperformance
- Avoids hard conversations to preserve relationships
- Lacks clear performance metrics and expectations
- Risks playing favorites
- Inconsistent accountability
- Needs a more structured roadmap for team development
How to Level Up:
- Implement a standard meeting framework with clear expectations
- Get comfortable setting (and sticking to) deadlines
- Schedule recurring performance reviews with every team member
- Set (and keep) professional boundaries (save the lunch dates for Fridays)
Resources:
- Download: Coaching Frequency Guide – Use this to categorize your reps by skill vs. will, so you know who needs your time, who’s coasting, and where to focus your coaching energy.
- Course to Take: Driving Performance With Goals – gives you tools to set clear expectations and build accountability without sacrificing team trust.
Knowing your type is step one. The real magic happens when you use that insight to grow.
The best sales managers aren’t stuck in one style, they flex. They coach intentionally, delegate purposefully, and lead with both heart and structure. Whether you’re a Powerhouse learning to let go, a Cheerleader learning to lean in, a Quarterback trading the playbook for coaching time, or a BFF building boundaries, there’s always a next level.
Better managers build better teams. Let’s get to work! Take the quiz here.