Sales Manager Lifesavers
60+ Sales Metrics to Track: Role-by-Role Guide to Activity & Performance
Sales metrics are your early indicators, your coaching roadmap, and your proof of sales training ROI.
They show you what’s working, where your team needs help, and whether your sales training investment is actually paying off.
But not all metrics tell the full story.
Activity is easy to measure and quota attainment is easy to celebrate. But by themselves, those numbers don’t tell you if reps are building skills, progressing deals, or gaining the confidence to hold real sales conversations.
That’s why we’re breaking down the top sales metrics to track by role.
Because every sales position contributes to pipeline and revenue in different ways, and tracking the right metrics helps you spot success earlier, coach more effectively, and tie enablement wins to revenue.
Here are the roles we’ll cover:
- BDR/SDR (Business/Sales Development Rep) Metrics
- ISR (Inside Sales Rep) Metrics
- AE (Account Executive) Metrics
- Account Manager/Customer Success Manager Metrics
- Sales Manager Metrics
Let’s take the guesswork out of performance and start measuring what matters.
BDR/SDR Metrics
Confidence shows up in activity. Skill shows up in conversion. That’s why the best BDR metrics don’t just tell you how many calls they made, but what actually happened after they hit “dial.” You won’t measure all of these, but pick 2-3 that are easily reported in your world. Focus on quantity and quality.
Here’s what you can track:
- New hire ramp – How long it takes to meet quota. Measure training effectiveness against past class baselines or use a control group. Four to six months to goal is average.
- Dials – Baseline activity matters, especially with newer reps. Just don’t stop here. Outbound BDR/SDR should average 50-100 dials a day.
- Dial-to-connect rate – Are they reaching humans? If not, it’s probably a data issue. Look for a 3-10% connect rate.
- Average talk time – Measure by call or daily total by rep. Good top of funnel calls are 2.5 – 10 minutes in length and focused reps should spend at least 2.5 hours/day on the phone.
- Connect-to-conversation rate – If a call lasts more than 2 minutes, that’s a human connection worth tracking. If you’re below 25%, reps need help with skills.
- Daily conversations – An average number of quality conversations per day (over 2 minutes). Aim for 3-5 conversations/day.
- Positive outcomes – A less common stat that can add “small wins” like accounts qualified, referrals gained, or follow-up meetings scheduled – anything that’s not quite a meeting. Aim for 25% plus.
- Meetings booked – Conversion from connect to meeting booked. Cold calls convert 2-5% on average, top reps and situations closer to 33%. Always pair with the next metric.
- Meeting show rate – AKA “hold rate.” Are these meetings actually happening? 50-60% is a good starting point, top performers come in around 90%.
- Percentage of qualified meetings – AEs will help you define what “qualified” means here and they’re always pickier than the SDR team. If more than 50% are being accepted, you’re winning.
- Lead to opportunity conversion – What percent of meetings actually wind up in the pipeline. An average is 1-3% of leads being added to the sales pipeline.
- Inbound calls – SDRs should be leaving messages, and good messages get returned. Great messages plus consistency will get up to 25% of calls returned.
- Call quality scores – This is where skill execution lives. Use your coaching rubric to track growth.
- Call engagement scores – A new AI feature from your conversational intelligence tool. No industry benchmarks yet, but like call quality scores, a smart add to your balanced scorecard.
These metrics help you go beyond the mindset of “more dials = better rep.” You’ll see who’s dialing scared, who’s winging it, and who’s actually applying the skills from training.
Skills That Move Metrics (and how to track them):
- Call intros and brush-offs – A great opener gets the prospect talking within the first 10 seconds and keeps them after an initial brush-off (it’s like an objection, but not). If they’re engaged, your talk time and connect-to-conversation increase along with your positive outcomes, and meetings booked. Take SWIIFT℠ Introductions That Work and Overcoming the Brush-off.
- Voicemails and prospecting planning – If callbacks and connects spike post-training, reps are implementing new and improved voicemail messages and email/social messaging. Take Messages That Get Returned and Planning for Prospecting.
- Deal qualification – When reps find the right people and pre-qualify leads by asking the right questions, the percentage of qualified meetings and meeting show rates spike immediately with lead-to-opportunity conversion following. Take Capture Contacts and Qualify and Categorize.
- Discovery – When reps improve questioning and engagement techniques vs. script reading and survey-taking, customers engage, and results show up in connect-to-conversion rate, daily talk time, positive outcomes, and meetings booked. Take Question Like a Pro to improve sales call discovery.
- Closing – SDRs lacking confidence struggle to have real conversations and ask for meetings. Reps improving in confidence and closing will show improvement in positive outcomes and meetings booked. Take Transitioning to Close to help close every call.
- Call quality – Not sure what to track in the conversation itself? Step one is using a standard coaching form so you can track progress.
When BDR/SDR training is working, reps get more voicemails returned, keep prospects on the phone longer, and confidently set next steps. These are your first signs that sales training or coaching is making an impact.
READ: How to Keep Prospects on the Phone
Inside Sales Rep Metrics
Inside Sales Reps do it all: prospect, qualify, demo, and sometimes close. That’s why tracking ISR performance requires more than just activity. You need to know if they’re creating pipeline, overcoming early objections, and setting up seamless handoffs (or closes).
Here’s what to track:
- New hire ramp – how long it takes to meet quota. Measure training effectiveness against past class baselines or use a control group. For ISRs six months is pretty average.
- Activity rate – Like SDRs, ISRs need a healthy outbound routine. Look for fewer outbounds than SDRs as ISRs balance demos, longer conversations, and orders, but insist on at least 10 outbound calls and 3-5x total activities including email/social per day.
- Initial call/lead conversion – Good initial calls convert into leads and follow up meetings. In addition to longer calls and talk time, top reps will convert above 30% of initial calls to a discovery call. Newbies and cold calls under 10%.
- Opportunities conversion – The conversion from discovery call into actual pipeline ranges from 10-30% on average.
- Demo conversion rate – Wherever “show and tell” falls in your cycle, watch what percent of opportunities progress past this stage. Benchmarks vary from 20-60%. Use your team’s history.
- Win rate – What percent of total opportunities in pipe ultimately close? Standards vary by industry and tenure from 15 to 50%.
- Follow-up attempts – Persistence matters, especially in a full-cycle role. Leads not getting at least five attempts are wasting money. Well-qualified leads should show 10+ attempts.
- Average sales cycle length – Are those opportunities moving forward? Or stalling out? Dividing the total number of days it took to close all the deals by the number of deals gives you baseline velocity.
- Pipeline generated – What is the average dollar amount added to pipeline per rep per period?
- Revenue/Profit – Actual revenue or margin closed. Use historical data for baselines and watch out for cyclicality.
- Average deal size – ACV/AOS depending on industry (average contract value/average order size).
- Quota attainment – Percent of goal achieved.
- Number of deals – Watch for efficiency and hustle by not just measuring dollars closed.
- Call/Demo quality scores – Customer engagement and rep skills are even more critical as deals progress. Measure standard discovery, communication, objection handling, demo, and closing skills. Keep coaching forms consistent between reps and teams.
*SaaS companies will track a few additional standard metrics like Customer Acquisition Cost, Lifetime Customer Value, MRR, and Customer Churn.
These metrics show you how effectively ISRs are turning conversations into qualified opportunities and moving deals through the pipeline. They help pinpoint where in the sales process training can create the biggest lift.
Skills to watch (and how to track them):
- Discovery and qualification – Reps who listen and adapt during discovery ask better follow-ups and surface real business pain. You’ll hear it in call recordings, and you’ll see the impact in higher opportunity conversion, shorter sales cycles, and higher pipeline revenue generated. Go deeper than SDR discovery with SWIIFT℠ Discovery Dialogue.
- Customer engagement – Great ISRs can lead a conversation and follow the customers’ lead – all while driving deals forward. That means next-level rapport, listening, and acting like a consultant. Mid-funnel engagement pays off in opportunity conversion, average deal size, and overall win rate. Focus on skills found in, My Role as a Consultative Seller.
- Demo/presentation – ISRs that give the same demo multiple times a day likely have low conversion rates. Great interactive presentations will pay off in call quality, demo conversion, average sales cycle, and pipeline generated. Take Demos That Don’t Suck to see lift here.
- Proving value – If you’re getting to the close but aren’t seeing conversion, we aren’t building enough value during the sales cycle. Reps who do this well have higher win rates, larger number of deals and faster sales cycles. Take Proposing with Value to help.
- Objection handling – Seasoned ISRs hear it all, from “This isn’t a priority right now” to dead silence. Tops performers will have higher follow up numbers, win rates, and quota attainment. Take Overcoming Objections and Selling With Stories to sharpen skills.
When ISR training is working, you’ll hear better discovery calls, improved demos, stronger objection handling, and confident next steps. And you’ll see it in stage-by-stage conversions in your pipeline.
READ: Call Bridging 101: Paving the Way for a Follow-up Sales Call
Account Executive Metrics
AEs get judged by the number, but that doesn’t tell the full story. You can close a big deal and still be losing pipeline behind the scenes. That’s why it’s critical to track not just what they’re closing, but how they’re progressing deals, and where they’re getting stuck.
Here’s what to track:
- Opportunity-to-close rate – A high rate means reps are moving qualified deals across the finish line; a low rate can reveal gaps in qualification or closing skills.
- Stage conversion rates – Show where deals are moving forward and where they’re getting stuck, helping you target coaching where it’s needed most.
- Days in deal stages – Longer times in a stage can point to stalled opportunities, poor follow-up, or hidden objections.
- Win rate – Indicates overall effectiveness at closing deals compared to total opportunities worked.
- Forecast accuracy – Builds trust in the pipeline by showing whether reps are correctly predicting which deals will close.
- Deal size and margin – Reveal whether reps are consistently landing high-value business or leaning on discounts to close.
- Pipeline coverage ratio – Highlights whether reps have enough in the pipeline to stay on track for quota.
- New opportunities created – Tracks how much pipeline reps are sourcing themselves versus relying on handoffs.
- Follow-up attempts per opportunity – Shows persistence in advancing deals and staying top of mind with prospects.
- Average sales cycle length – Gives insight into deal velocity and whether reps are moving opportunities forward efficiently.
- Call/demo quality scores – Reflects the strength of rep communication, objection handling, and ability to progress deals during live interactions.
These metrics give visibility into each stage of the sales cycle so you can see where deals are progressing smoothly and where they may need coaching or additional support to move forward.
Skills to watch (and how to track them):
- Discovery and uncovering customer needs – Great AEs don’t ask generic questions. They dig until they uncover the real business pain. When this skill is sharp, you’ll hear deeper conversations in call recordings and see more accurate opp qualification, faster stage movement, and fewer stalls after demos. Take Question Like a Pro to learn advanced questioning techniques that turn scripts into real, value-driven conversations.
- Demo/presentation – A strong demo isn’t about showing every feature, it’s about telling the right story. Great AEs tailor the conversation to the prospect’s needs, show the exact value they care about, and make it easy for them to see themselves using your solution. You’ll see this reflected in higher stage conversion rates, stronger call/demo quality scores, and more stakeholders engaged after the call. Take Demos That Don’t Suck to learn how to engage, adapt, and close more deals from your presentations.
- Demonstrating customer value – It’s not about pitching, it’s about showing how your solution impacts their business. If reps are demonstrating value well, you’ll see less discounting, stronger deal size, and customers pulling in stakeholders instead of ghosting you. Take What Customers Care About to map buyer motivators to your solution and propose in a way that resonates.
- Driving deal momentum – If deals are sitting in the pipeline, it’s not because they’re bad deals, it’s because they’re not being worked. AEs who drive momentum confirm mutual next steps, secure time on the calendar, and keep the deal moving. You’ll see this in shorter days in stage, cleaner notes in the CRM, and fewer “stuck” opportunities with no recent activity. Take Getting Deals Moving to keep deals advancing and commitments in place.
- Handling objections – Objections at this stage often signal deeper unaddressed concerns. Reps who respond effectively keep deals alive and increase win rate. Take Overcoming Objections to apply a proven four-step process that addresses concerns and moves the conversation forward.
- Consultative selling – AEs who operate like business advisors uncover more opportunities and face less pricing pressure. Look for this in higher-quality CRM notes, increased stakeholder engagement, and higher ASP (average selling price). Take My Role as a Consultative Seller to sharpen your business advisory approach and build trust faster.
- Proposing with value – When done right, proposals clearly connect your solution to the customer’s goals. Look for higher proposal acceptance, fewer stalls, and improved close rates. Take Proposing with Value to create compelling proposals that drive decisions.
- Closing confidently – Reps with strong close skills don’t beg for business, they ask with clarity and confidence. You’ll hear it in recorded calls and see it reflected in win rate, number of deals, and reduced discounting. Take Closing Confidently to find your go-to close statements and build muscle memory for asking.
When account executive training is working, you’ll see cleaner pipeline stages, stronger discovery, and tighter forecasting. It’s less “I think it’s coming in” and more “Here’s where we are, here’s what’s next.”
WATCH: How to Fix the Top 5 Mistakes Made During Sales Demos
Account Manager/Customer Success Manager Metrics
Account Managers and Customer Success Managers are the face of your brand after the deal closes. But renewals and growth don’t come from check-in emails and good vibes. These reps need to earn trust, uncover new opportunities, and consistently demonstrate value. That’s how you keep customers, and grow them.
Here’s what to track:
- CSAT (customer satisfaction score) – Tracks how happy customers are with your product or service. However you measure it, monitor changes over time by rep to spot trends and coaching opportunities.
- NPS (net promoter score) – Measures customer loyalty and likelihood to refer you to others. A higher score can indicate strong relationships and a healthy base of brand advocates.
- CLTV (customer lifetime value) – Shows the total revenue a customer is expected to bring over the course of the relationship. Helps you prioritize and protect high-value accounts.
- Customer retention rate – Indicates what percentage of customers stay with you over a given period. High retention signals strong account management; declining retention may point to service gaps.
- Churn – Tracks the percentage of customers leaving. Monitor closely to flag at-risk accounts early and take action to prevent turnover.
- Renewal rate – The ultimate retention metric. Shows how often contracts are successfully renewed and can highlight patterns by rep or segment.
- Expansion revenue – Measures revenue growth within existing accounts. A rise here means reps are finding and closing new opportunities in their current book.
- MRR (monthly recurring revenue) growth – Tracks the increase in monthly recurring revenue from existing customers, indicating steady, predictable account growth.
- Average purchase value – Look at the average transaction size. Growth here often signals effective upselling and cross-selling strategies.
- New SKUs – Measures the number of purchases in new product or service categories, showing whether accounts are broadening their adoption.
- Active buyers – Counts the number of individual buyers within an account making purchases. Growth suggests successful expansion to new departments, teams, or locations.
- Customer health score – Combines product usage, engagement, and satisfaction into a single view to identify accounts at risk and those ready for expansion.
- CES (customer effort score) – Tracks how easy it is for customers to get what they need from your team. Lower effort correlates with stronger loyalty.
- Activity-to-engagement ratio – Compares how much time you spend with customers versus the quality or impact of those interactions. Reminds reps that more meetings don’t automatically mean more value.
- Time to renewal/expansion opportunity – Measures how long it takes to uncover new value and growth potential in an account, helping you assess how proactive your AMs/CSMs are.
These metrics provide a clear picture of account health and growth potential, helping you spot risks early and identify where strategic conversations can open new opportunities.
Skills to watch (and how to track them):
- Gaining referrals – Loyal customers don’t just renew, they advocate. If reps are asking the right way (and at the right time), you’ll see an uptick in warm intros and referral opportunities logged in the CRM. Take Gaining Referrals to build confidence and a proven process for turning satisfied customers into your best lead source.
- Uncovering new opportunities – Great AMs don’t wait for customers to raise their hand. They ask smart questions, connect dots, and bring proactive solutions to the table. Track this by monitoring qualified expansion opportunities created and account mapping activity. Take Uncovering Sales Opportunities to uncover needs and position solutions that drive account growth
- Increasing wallet share – If reps are building trust and delivering value, you’ll see increases in upsell, cross-sell, and product adoption across existing accounts. Take Growing Account Revenue to create targeted growth plans and confidently expand within your book of business.
- Customer engagement – Great AMs create value in every interaction, not just touch base calls. Measure follow-up rates, meeting conversion, and customer survey comments. Take Engaging Your Customers to build excitement and keep customers invested in the relationship.
- Consultative selling – Top AMs bring insights, not just checklists. Listen for strategic questions in call recordings and look for greater opportunity conversion and deal size. Take My Role as a Consultative Seller to elevate customer conversations and earn trusted advisor status.
- Business acumen – AMs who understand the customer’s industry, org structure, and goals hold better conversations. You’ll see longer calls, better engagement, and more strategic expansion plays. Take Business Acumen to speak the language of executives and lead more impactful discussions.
When account manager training is working, you’ll see AMs running stronger account reviews, finding new revenue inside existing customers, and proactively addressing risks before they become churn. They’re not just retaining customers, they’re growing wallet share, keeping renewal pipelines clean, and avoiding last-minute surprises.
READ: How to Ask Existing Customers for a Sales Referral
Sales Manager Metrics
Good managers build great reps. That’s why your manager scorecard should go beyond team quota and focus on how well they coach, develop, and retain talent. The best metrics show whether their reps are getting better, faster, and sticking around. You don’t need all of these, but pick a few that help you measure both leadership impact and team performance.
- Ramp time – How long it takes new hires to hit quota; use past averages or compare trained vs. untrained cohorts to track manager impact.
- Percentage of team to goal – The percentage of reps consistently hitting their number; a sign of strong leadership and accountability.
- Promotion rate – Tracks how many reps are promoted from the manager’s team; high rates show strong development and bench-building.
- Retention and engagement – Use surveys or attrition data to gauge whether reps are staying and thriving under their manager.
- Forecast accuracy – Compares manager forecasts to actual revenue; accuracy indicates strong deal coaching and pipeline visibility.
- Team skill improvement – Use training assessments, call scores, or certifications to track rep skill growth over time.
- Consistency of performance – Measures if the team hits quota quarter after quarter vs. riding the rollercoaster; stability = good leadership.
These metrics measure a manager’s impact on team development, consistency, and overall performance, giving you insight into both leadership effectiveness and team health.
Skills to watch (and how to track them):
- Coaching – A strong coaching culture improves rep performance and morale. You’ll see the impact in faster ramp time, higher call quality, and consistent team skill improvement. Take Call Coaching 101 to build a positive, interactive coaching style that leaves reps confident and ready to apply new skills.
- Time management – Burned out or reactive managers cancel 1:1s, skip coaching, and lose focus. Look for low coaching frequency, weak consistency of performance, and manager survey scores to identify this early. Take Own Your Day to prioritize what’s important over what’s urgent and create space for high-value management activities.
- Goal setting – Managers who translate team targets into clear daily expectations drive better accountability and percent of team to goal. You’ll also see more consistent performance over time. Take Driving Performance with Goals to break big goals into actionable milestones and behaviors that stick.
- Having tough conversations – Strong leaders don’t let poor performance slide. This skill shows up in better team retention, improved engagement, and shorter time-to-improvement for struggling reps. Take Having Difficult Conversations to gain a framework and confidence for handling the hard talks effectively.
- Developing talent – Growth-minded managers build the bench. High promotion rates, better rep retention, and higher engagement scores are clear signs this skill is in play. Take Developing Your Team to learn practical ways to inspire and grow your people between training events.
- Strategic deal planning – Managers who support reps with territory, lead, and deal strategies improve forecast accuracy and drive stronger quota attainment and rep confidence. Take Sales Strategy Meetings to guide reps through targeted, high-impact planning sessions that move deals forward.
- Hiring & onboarding – Smart hiring and strong onboarding reduce early attrition and shorten ramp time. Track first-90-day performance and how often their hires stick. Take Hire Like a Rockstar to build a best-practice interview and selection process tailored to your team.
- Meeting effectiveness – Organized managers who run purposeful meetings drive stronger consistency of performance and better engagement. Check for cadence completion and team survey feedback. Take Essential Manager Meetings to create a proactive meeting cadence that keeps your team on track and engaged.
When sales manager training is working, you’ll see faster ramp times, stronger forecast accuracy, and more reps hitting quota consistently. Team skills improve quarter over quarter, retention goes up, and promotions happen more often. Great managers coach with purpose, run effective meetings, and keep their teams performing without the burnout rollercoaster.
READ: Build Your Sales Manager Cadence (& Save Time and Stress)
Tracking the right sales metrics isn’t just about managing performance, it’s how you prove what’s working, where to coach, and when your sales training is actually paying off. Whether you’re investing in new training programs or reinforcing skills with your current team, these metrics are your clearest window into what’s driving real behavior change and revenue impact. Because when you can connect skill development to pipeline movement, you’re not just improving performance, you’re proving sales training ROI.
Subscribe to our email list to receive new content, webinar invites, and training offers.
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).
Subscribe to our email list to receive new content, webinar invites, and training offers.
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.
Subscribe to our email list to receive new content, webinar invites, and training offers.
What Type of Sales Manager Are You? (& How to Make It Your Superpower) [Webinar Recording]
What Type of Sales Manager Are You? (& How to Make It Your Superpower)
[Video Recording]
Your Sales Manager Survival Kit [Cheat Sheets]
Your Sales Manager Survival Kit
[Free Resources & Cheat Sheets]
How Tenured Sales Leaders Took Their Coaching to the Next Level
At Dun & Bradstreet, some of the most tenured sales managers, leaders with over 20 years of experience, had a breakthrough they didn’t see coming.
John Healy, one of our Sales Advisors, spent a full day with the team, leading a session on Driving Performance with Goals (a longtime manager favorite). But this wasn’t another pep talk about why goals matter. It was hands-on. Practical. Focused on building real connections between daily activities, KPIs, and long-term outcomes.
For many in the room, it was the first time the dots fully connected.
The real shift didn’t come from slides or lectures. It happened inside The Sales Bar by doing the work.
The managers rolled up their sleeves and practiced how to:
- Map goals to rep behaviors
- Build coaching cadences that actually stick
- Practice conversations before trying them live
- Lead like strategic managers, not just task supervisors
By the end of the day, those same leaders were mapping out new team strategies, role-playing coaching conversations, and sharing real-life examples of how they would start applying new approaches immediately.
They weren’t just talking about change. They were leading it.
Why did it work?
Because they didn’t just learn about managing performance. They experienced it.
The Sales Bar isn’t just another resource. It is where even the most experienced sales leaders go to sharpen their edge and lead with purpose.
Subscribe to our email list to receive new content, webinar invites, and training offers.
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.
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?”
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.”
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.”
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?”
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
Subscribe to our email list to receive new content, webinar invites, and training offers.
Building a Top-Performing Sales Team [Webinar Recording]
Building a Top-Performing Sales Team
[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.
Her mission is to change lives by supercharging people’s careers and helping them love coming to work. When we feel confident and successful at work, everything is better, right? Known on the speaker circuit for her “No B.S.” style and spunk, look for LB to make you laugh, keep things moving quickly, and help you take immediate action with her tactical tips and insights.
Devyn Blume
Sr. Account Executive
Allego
Devyn is a Sr. Account Executive at Allego with 8 years of experience in sales, specializing in consultative selling and client relationship management. Throughout her career she has excelled in driving revenue growth, building strong customer partnerships, and leveraging sales technologies to streamline processes.
At Allego, Devyn focuses on delivering innovative sales enablement solutions, helping teams optimize training, onboarding, and content sharing. With expertise spanning multiple industries, she is a trusted advisor to clients seeking to enhance sales performance through technology-driven solutions.