How do you build a top-performing sales team? Short answer: Skills. Confidence. Coaching.
Every sales team has a few all-star reps. The ones who just get it and crush it. The question is, how do you clone that kind of success?
Here’s the truth: some people are born with drive, curiosity, and that inner fire to win. But top-performing sellers aren’t just born, they’re developed. They learn the skills, build the confidence, and have managers who coach them along the way. The good news? Every bit of that can be taught.
If your reps are struggling to find the right contacts, freezing up when someone actually answers the phone, or taking forever to ramp, it’s not a talent problem. It’s a skills and confidence problem.
So, whether you’re building a team from scratch or helping seasoned sellers hit the next level, here’s how to turn potential into performance.
Getting Started: What’s Holding Sellers Back?
Before you can grow a high-performing sales team, you have to figure out what’s slowing reps down. For most, it starts with confidence. New sellers don’t know the language yet, feel unsure about the tools, and get stuck just trying to figure out who to call.
Here’s what sales leaders say are the top challenges:
Fear of the phone
Low business acumen
Poor time management
Struggling to find the right contacts
Stalled or ghosted deals
And even when they do reach the right people, getting them to engage (and knowing what to say next) isn’t always natural.
Confidence doesn’t just appear. It’s built, one conversation, one small win at a time.
Build Confidence from Day 1 by Training These Skills
New hire sales training often tries to do too much. But what sellers need most in their first few weeks is confidence, the kind that comes from actually knowing what to do and say in real situations.
Skip the deep dives into quoting systems or pricing battles. In the beginning, focus on the basics that make up 90% of their day:
Leaving voicemails that get a callback
Knowing what to say when someone actually answers
Keeping prospects on the line
Handling “Who the heck are you with?”
Finding the right people and getting them to engage
Delivering your value prop with confidence
Capturing key contacts on the call
That’s the heart of just-in-time sales training. Teach what reps need for their first 30 days, not their first 300.
Tip: When new reps leave training feeling confident, they come back hungry for more. That’s how you build a learning culture and ramp faster.
One of the most effective coaching tools out there is the Pause Game. It’s simple and powerful:
Play any recorded call (it doesn’t even have to be their own)
Pause every 10 seconds
Ask two questions:
What’s the customer thinking right now?
What would you do next?
This exercise pulls reps out of their own heads and into the customer’s world. It builds active recall, which science shows is five times more effective than passive learning.
The game teaches reps when to apply knowledge, not just what to say. That small shift in awareness can shave weeks off ramp time.
Tip: It’s not just about knowledge. It’s about retrieval. Helping reps recognize when to use the right skill is what separates good from great.
Create call libraries and show reels of top reps in action
Run timed CRM drills during training to build speed and multitasking skills
Digital Sales Rooms (DSRs) are must-have sales tools. These microsites let sellers organize resources, track buyer engagement, and keep deals moving with mutual action plans and real-time visibility.
Tip: Tools like DSRs don’t just help reps. They make it easier for buyers to stay informed and move deals forward. That’s a win-win.
Retention, Career Paths, and Coaching the Coaches
If you want to keep your top reps, you have to do more than teach them how to sell. You have to show them what’s next.
Reps are motivated by success stories, recognition, and growth. So give them that:
Share real win stories across the team to celebrate success and boost morale
Create safe spaces for loss stories to promote learning and vulnerability
Build clear career paths from BDR to AE to manager, with skills mapped at every level
Coaching plays a massive role here. Too many managers run 1:1s, review pipeline, and put out fires, but never actually coach.
That’s why developing your managers matters. Coaching certifications give them a repeatable system to build skills, boost confidence, and grow their people.
Tip: If managers don’t know how to coach, reps don’t improve. Equip your frontline leaders to develop people, not just push deals.
Just-In-Time Training, Simplified Tech, and Manager Reinforcement
Let’s be real. Most reps are buried under too many tools and use none of them well. The average tech stack is a juggling act, not a system.
Keep it simple. Your learning, content, and call-intelligence tools should actually talk to each other so managers can move fast, coach smarter, and see what’s working.
Manager dashboards should show trends, not snapshots; who’s improving, who’s stuck, and where to step in.
And here’s the kicker: about 90% of what managers say in a 1:1 is forgotten within a week. Real learning sticks when it’s reinforced, coached, and repeated until it becomes a habit.
This article is based on insights shared during a Sales Shot webinar featuring Lauren Bailey and Devyn Blume, Sr. AE at Allego. Watch the full session here.
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In the past decade, inside sales has been out-pacing field sales by a 10-15x ratio. Scalability is a challenge inside sales leaders will continue to face for years to come.
While I normally focus on building your process, today my job is to talk about the people angle. Although, a good half of my people’s suggestions are process suggestions! Allow me to highlight the top 3 common pitfalls we have all faced when trying to scale your inside sales team and a few outside resources that can help.
Pitfall #1: The success of a massive growth number will live or die in a rep’s ramp time.
Ramp time means something different to each company. It could be time to quota, paying for their overhead, or something unique to you. Whatever your ramp goal, you’ll be creating projections to hit a 1.5x, 3x, or even 5x number and you’ll be doing it with a new headcount.
That means your success hinges on the ability of your headcount to:
Be hired on time
Be trained on time
Hit goal on time
Really dig into your new hire training program, and start doing it six months before your first hiring wave. If you haven’t onboarded recently, check out our sales rep onboarding best practices. And if your offices are still remote, brush up on virtually onboarding new sales reps
Pro Tip: Hire a sales-focused training leader NOW. Most new hire training programs need a LOT of work, and the good ones can cut your ramp time by HALF.
Pitfall #2: We don’t change our hiring process.
Even if you previously onboarded an awesome team that is still with you today, your process likely needs a few tweaks before being pressure-tested during scaling. We usually see breakdowns in two key places:
The pool isn’t as deep any longer. We are in a hiring crisis, folks. Many companies stole great talent when they were new on the scene, but now they’re competing for headcount like everyone else. So even if the number of candidates and job postings are similar, you may find the depth of talent more shallow.
The hiring and onboarding process wasn’t built for volume and is probably too dependent on your managers (but the slew of new hires on the floor will need them more too!) At launch, these managers had all kinds of time to hire. If you triple your model (then double it for the shallow talent pool), think of how many hours per day they will be in interviews. Ouch!
Pro Tip: Pull hiring out of HR and to a recruiter – even if you need to re-appropriate a sales headcount. You need someone doing passive recruiting on the front end, AND who can handle a phone screen for sales. It’s the only way to free up your managers’ time. Make sure you tie the recruiter’s compensation to the RIGHT hires that align with your goals, instead of fighting a recruiting company’s goal of straight-up bodies. I’ve seen way too many new hire classes filled with “live bodies” by recruiters only to have to rehire a replacement class a month later. Sales leaders make no mistake, the need to retrain or rehire is how your hiring goals will be perceived in a culture of scale.
Also, check your hiring process. It should look like your pipeline, with your managers involved only toward the final stages. Oh, and let them hire their own team, OK? (Managers, you can send your cash directly to the Factor 8 HQ for that tip).
Pitfall #3:Develop your managers, NOW.
I’m watching a friend’s floor triple in size right now. They’re super successful and swimming in leads. They need a headcount to maximize the revenue. What they’re missing is strong leadership, definitions of what ‘good’ looks like, and consistency among the management team. And folks, it’s being held together with duct tape and rainbows right now. These managers are SO (say it like a teenage girl) green. Everyone runs different reports, they all manage a different sales process, there are seven disparate call methodologies, no one can forecast because pipelines are atrocious, teams are mixed and matched constantly (because managers are leaving the chaos!) and no two are managed the same. I’d say they’re all marching to a different beat, but no one remembered to hire the drummer.
Pro Tip:Hire a drummer…as long as that drummer is a series of documented processes (management cadence, performance improvement, sales handoffs, sales process to name a few). Then, TEACH your managers how to execute against them. You and I both know these people were reps five minutes ago. They need training. They need help being better leaders (or you’ll quickly wind up back at #1 hiring even more bodies). Reps join companies and quit bosses, right? New managers are going to FLAIL in a rapid-growth environment, and your reps will be confused, frustrated, and complain about a lack of development (which also happens to be the number one reason reps leave).
So, save yourself some time and a headache by updating your training program, and getting the professionals to help you with hiring, and developing those managers! I promise, the work now will be worth it once your sales floor is full (and stays that way!).
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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.
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.”
When I became the Global Head of Enablement at SAP, I was given one monumental task: launch outbound virtual sales training FAST.
I had no team. No curriculum. And a deadline that did not care.
In four weeks, 37 reps were scheduled to sit in a classroom in Barcelona. And I had nothing. No content. No internal resources. No time to build it all from scratch.
So I did what most enablement leaders in that situation do. I started shopping for sales training.
What I found was the same thing you still see everywhere today. A standard two day workshop. One version for Sales 101. One for Sales 201. One for managers. One for leaders. A little pre-work, maybe a little post-work, but essentially a one-size-fits all experience that was not designed for our motion or our customers.
When I asked vendors for customized sales training, I paid an extra ten thousand dollars and got two role plays printed on paper and shoved into the back of the workbook.
That was the “customization.”
It was not just frustrating. It was unusable. I did not want a vendor. I needed a partner. I needed content that actually fit our inside sales training reality and that my team could reuse, adapt, and build on, not a one time event.
That experience stuck with me. It shaped how I think about sales training, and it is a big reason I am on a mission to make customizable sales training the norm instead of the exception.
If you have ever sat through generic sales training, you already know why it fails.
Most programs are built for delivery efficiency, not real world application. They are designed so a trainer can fly in, deliver the same deck to a different audience, and fly out again.
On paper, it looks like this:
One standard curriculum
One format, often a two day workshop
One path, regardless of role or segment
One moment in time, then it is over
In reality, this creates three big problems.
#1 Engagement
Reps and managers are busy and overloaded. The human brain is always scanning for reasons not to change. The second they hear an example that does not match their buyers or their sales cycle, they check out. “This is for field sellers.” “Our buyers are nothing like that.” “This feels like theory, not inside sales training.”
#2 Application
Even great ideas die if the rep has to translate them alone. When training is generic, you are asking each seller to figure out how to apply it to their role, their accounts, and their conversations. A few high performers will do it. Most will not.
#3 Retention and ROI
We know from learning science that people forget the majority of what they hear in class within days if they are not actively recalling and using it. If there are no real calls, no role specific activities, and no coaching built around the new skills, the investment evaporates fast.
That is why truly customizable sales training matters. Not because it sounds fancy, but because relevance is what keeps reps engaged long enough to try something new, and trying is the first step toward results.
The Real Build vs. Buy Dilemma For Enablement Leaders
If you run enablement or revenue, you are caught in a familiar trap.
Option 1: Build your own sales training
You control the message and the motion
You align to your process, customers, and tech stack
You can design role specific paths for BDRs, AEs, AMs, and managers
But you also run into the reality:
It takes months, sometimes years
Your team already has a full time job
Internal credibility can be uneven
Content gets outdated faster than you can update it
Option 2: Buy external sales training
You get outside expertise
You get something faster
You get a facilitator with instant credibility
You get structure you did not have to build
But the tradeoffs are real:
Content is often generic and one size fits all
It is hard to plug into onboarding and ongoing development
You often do not own the materials
Two years later the playbook and slides are still sitting where you left them
Enablement leaders live in that tension. You want the speed and quality that comes from buying, but you also need the control and customization that comes from building.
Revenue leaders feel it from a different angle. They see the price tag and ask if this sales training will move pipeline, conversion, and quota attainment. The answer depends almost entirely on whether the content feels relevant enough to use and simple enough to apply quickly.
That is the heart of the build vs. buy dilemma. It’s not about training for training’s sake. It’s about behavior change, time to impact, and whether the organization will actually adopt what you invest in.
Why Customizable Sales Training Matters For Both Enablement And Revenue
This is where customized sales training and modular sales training become a strategic lever, not a “nice to have.”
For enablement leaders, customizable sales training means:
You can align content to your stages, roles, and motions
You can plug modules into onboarding, everboarding, and refreshers
You can keep building on the same foundation instead of starting from zero every year
You get a shared language for managers to coach to
For revenue leaders, inside sales training that is truly customized means:
Faster ramp and shorter time to first meeting and first deal
Higher adoption because reps recognize themselves in the examples
Less rework and less “shadow curriculum” created by individual teams
Better visibility into what “good” looks like on actual calls
At its best, sales training is not a one time event. It is a system that combines short, tactical learning, manager coaching, live call practice, and reinforcement activities over time.
Generic content cannot support that system. Customizable sales training can.
What Customized Sales Training Actually Looks Like At Factor 8
This is exactly the gap we’re filling at Factor 8.
Instead of a single, fixed workshop, our inside sales training is built from more than 40 mini modules that we mix and match based on real data about your team. We start with an assessment. We listen to calls, review metrics, talk with leaders and reps, and identify where deals stall and where confidence breaks down.
From there, we design a custom enablement plan that often includes different paths for different roles. A BDR, an AE, and a manager should not all sit through the same day and hope to extract what they need. Each role gets the skills and scenarios that match their reality.
Customization shows up in the delivery too. The decks do not talk about “selling ice to Eskimos.” They use your buyers, your stories, your competitive landscape. Activities, role plays, and even customer logos are built around your sales motion. Reps often bring real calls into the room. We give feedback on actual conversations, not hypotheticals.
We also use a blended learning model that puts application at the center. Reps take short eLearning first to learn the core concepts. Then they complete customized homework that applies those concepts to their world, for example writing their own intros or value statements. When they come to the live workshop, they are already working from their own talk tracks and we coach them up from there.
After class, we keep going. Reps and managers come back together for accountability sessions where we review recorded calls, give next level feedback, and layer in more advanced tips. Managers then meet with us separately so we can calibrate what “good” sounds like and make sure they are reinforcing the skills in one on ones, huddles, and team meetings.
That is customized sales training in practice. It is inside sales training that is specific to your world, built to be used, and supported by your managers, not just a trainer.
Now here is where the model really shifts for enablement.
We heard the same thing from leaders again and again. They loved the training. They loved the outcomes. And they wanted more control. They wanted to keep building on the content with their own voice, their own products, and their own expertise.
With All Access, you still get the full Factor 8 experience, including the assessment, the modular curriculum, and our trainers. But you also get the editable soft copies of our workshops and materials, along with train-the-trainer support and LMS ready files.
That means:
You can license customizable sales training content that already works
You can brand it, adapt it, and plug it into your own LMS or run it in ours
You can build role-based paths for reps and managers without starting from scratch
You can keep content evergreen by updating it as your motion evolves
In plain terms, we help you solve the build vs. buy dilemma.
You get the speed, expertise, and credibility of buying outside sales training. You get the control, flexibility, and ownership of building your own. And your reps get inside sales training that finally feels like it was made for them.
If you are tired of choosing between generic workshops and year long build outs, this is the middle ground. Customized sales training that is modular, practical, and actually yours to keep.
Are you looking for customizable sales training?
Contact us today to learn about our customizable virtual sales training programs available for reps (and managers).
What’s the most overlooked factor in sales growth? Your frontline sales managers.
They influence every deal, every rep, every forecast, and yet about 60% of new managers report they never received training when they stepped into leadership.
Let’s stop looking past the obvious. Your frontline managers are the secret to scaling sales growth.
If you want more reps hitting quota, more deals converting, stronger forecasts, and less burnout across the board, it starts with your managers. Not your tech stack. Not your latest AI tool. Not another rep enablement platform (though these are important and we love them, check out our friends at Allego).
I’ve worked with thousands of sales teams and here’s the hard truth. Most companies are investing in everything except the role that has the biggest impact on team performance and revenue growth.
And when we flip that, the results are massive. We’re talking 20 to 47% increases in rep conversion rates. And we didn’t even touch the rep. Just by developing their manager.
So if you’re planning for growth, keep reading. Because managers aren’t a bottleneck. They’re your biggest growth engine.
1. Managers Bring Consistency (and That’s What Scales)
Change is part of growth. Reps switch teams. Territories shift. Comp plans evolve. But in the middle of it all, your frontline managers keep the team focused, engaged, and aligned.
That only works when they’re supported.
Too often, every manager ends up running their own playbook. Not because they want to, but because they’ve never been shown what “good” looks like. And even when you have playbooks, they don’t get translated into everyday actions and team rhythms.
Here’s where the cracks usually show up:
Hiring: Everyone’s looking for different things. Even with a profile in place, managers need support identifying what good sounds like in an interview.
Performance management: Breaking down a big quota into measurable KPIs isn’t intuitive. And very few new managers have been trained to do it.
Rep engagement: Some managers meet weekly. Some meet monthly. Some skip 1:1s entirely. Most spend time reviewing pipeline, not developing skills or coaching.
Pipeline hygiene: Definitions for deal stages vary across teams. That makes forecasts unreliable and coaching hard to scale.
Consistency is what turns momentum into real, scalable growth. And it starts at the manager level.
Give them the tools to:
Hire with confidence using a shared rubric
Set goals and track KPIs that actually drive performance
Run a standard meeting cadence that blends coaching, performance, and career conversations
Clean up pipeline processes so everyone’s speaking the same language
Even tenured managers benefit from this kind of clarity. One enterprise team we worked with had over 10 years of management experience and still walked away from this training saying, “I wish I’d had this years ago.”
2. Great Managers Build People, Not Just Pipelines
Most sales managers were promoted from rep roles. And as reps, their entire world revolved around winning. So when things get tough, what do they fall back on?
Closing the deal.
They hop on the call. They take over the demo. They second-voice the close. It’s not bad intentions, they’re just doing what worked for them. But when a manager becomes the deal hero, the team stops learning.
And that’s when reps leave.
They leave when they don’t feel developed
They leave when they’re not hitting quota
They leave when they don’t have a strong relationship with their manager
The revolving door hurts growth. Every open seat is lost pipeline. Every green rep takes months to ramp. Every exit chips away at morale.
What helps? Redefining the manager role and giving your leaders a new toolkit.
Help them shift from deal-doer to rep-developer
Give them interaction frameworks like COACHNso coaching doesn’t feel like guesswork
Recognize managers for building people, not just saving quarters
Because a manager who builds skill, confidence, and trust is someone who retains reps, not replaces them.
We all love to say coaching is the silver bullet. And it is. But only when it’s done well.
Real coaching moves the needle on performance, confidence, and retention. But too often, what we call “coaching” is just a pipeline review in disguise.
If you’ve ever listened in and heard:
The manager doing all the talking
A rep leaving with three disjointed to-dos
A session that feels more like a performance review than a development convo
Then chances are, your managers need support here.
The most common trap? The Mini-me. That’s the manager who coaches every rep to be a version of themselves. It works for the one or two reps with the same style. Everyone else gets frustrated, disengaged, or overlooked.
Good coaching is consistent, rep-centered, and rooted in skill development, not deal rescue.
That’s why we don’t treat coaching like a one-hour workshop. It’s now a six-hour, three-part course here at Factor 8. Because shifting behavior and building confidence takes time. And when it clicks, reps perform. They stay. And they grow.
If You’re Skipping Manager Development, You’re Skipping the Scale
Let’s be honest. The biggest miss isn’t the manager. It’s us.
We’ve skipped the basics. We assume managers will figure it out because we did. We prioritize tech over training. We fix people problems with process or platform investments.
But if you want more reps to hit quota, you don’t need a new tool (yet). You need stronger conversations first.
That comes from skilled, supported, confident managers.
Most reps today get a sliver of what they need in onboarding. Then they’re tossed five tools and a quota. They’re still learning the basics. And the person who owns the rest?
Their manager.
So let’s invest in them. Train them. Coach them. Give them a framework, a cadence, and a community. Make development part of the rhythm, not a one-time event.
Because your reps aren’t going to grow if your managers aren’t growing too.
Managers are the secret to scalable revenue growth. Let’s stop hoping they figure it out, and start helping them knock it out of the park.
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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.
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 andOvercoming 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 Proto 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 Closeto 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.
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.
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.”
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.
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.
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.
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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.
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.
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.
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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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.
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After you’ve hired a sales training vendor, there are a series of questions you need to answer in order to ensure you’re getting the most out of your sales training investment, like:
How do I maximize sales training ROI?
How do I measure training success?
How do I get results FAST?
Having been both the vendor and the buyer in this equation, I definitely have some insight to share. I’ve made mistakes as the Training Director hiring a sales/sales leadership training vendor, and I’ve had clients do some really smart (and less than smart) things.
Although I could write about this topic forever, I’ve narrowed it down to my top 5 tips to maximize your sales training investment.
1. Customize the Customization. Then customize that. Twenty years ago, I paid a vendor $15,000 extra to customize the training for my company. I spent countless hours sending them examples, marketing data, and websites. I forwarded redacted emails and unpublished case studies. I just KNEW they would get the “real feel” for how special our snowflake was. The result?
The vendor added one half-page sheet to the back of the workbook with two custom role plays. TWO! The pages weren’t even numbered with the rest of the workbook. Total afterthought! Literally, nothing else was custom.
Ready for the vendor flipside? Six years ago we up-leveled all our workbooks for Factor 8. This meant I couldn’t build custom workbooks from scratch anymore for clients (the downside of totally custom is a less professional look – even a few errors). Now each of our course workbooks of about 10 pages has around 15 sections in bold red font that our Advisors tailor prior to delivery. It might be the customer’s language, an industry example, a customer voice example, specific sales objections, etc. During the live interactions, our coaches play their sales calls, coach actual delivery, and will give custom samples/scripts of every skill. That’s customization!
Tip: Get an actual list of what is tailored to your organization, its format, and when/how it is delivered.
2. Require Manager Involvement. Note: I didn’t say attendance. You need attendance AND involvement! Back when I was delivering training in an enablement organization, we were afraid to invite all the sales managers to our training. They were so busy and important (and let’s be honest, a little rude). As I gained more confidence, I would meet with them 1:1 after the training with tips on what we trained and what to look for. As I got busier, I would schedule a 15-minute meeting so I could do this all at once. When I was put in charge, I required them to come AND met with them for 30 minutes afterward.
Guess what? They still couldn’t coach the skills. Sure, they attended the training, but they didn’t participate. They didn’t come and play to win as if they, too, would be graded on their adaption of the skills. They half-listened, did some email, smiled and nodded, and stole the stage as often as possible to give sage advice.
Vendor Flipside: At Factor 8, we meet with managers before the training, require attendance at the training, train the managers on how to coach the skills after the training, give managers 3+ tools to make it easy to support and coach the training, then do a follow-up meeting with the managers on how skills went, AND certify the managers to certify the reps on the skills. It may seem like overkill, but trust me, it works.
Your ROI will be cut in half if your managers aren’t underlying the importance of using the new skills and coaching their execution. Go overboard making sure they are trained, incentivized, and supported by your vendor to do this!
3. Measure Your Heart Out! If you aren’t crystal clear on the results, KPIs, and metrics that should be impacted by the training, then you’re not ready to outsource sales training. (Really, a vendor just said that!) In fact, ask the vendor what numbers they expect to move with this engagement (and don’t hire them if they don’t know!) At some point, you’ll have to show your sales training ROI, so define during the interview stage what success looks like and then go get a 3-6 month baseline on these metrics. As a training manager, I was nervous early in my career to do this. It only took one sales leader saying, “You are not solely responsible for the 35% uptick in XYZ…!” for me to start backing down and measuring success anecdotally or with smile sheets. As I grew in my career, all I did was add two words: “contribute to.” If we measure pre and post, we can all SHARE the credit!
Vendor Flipside: I love a case study. Number one reason I don’t have one on every client? They don’t provide us with their reporting. The leader pulls the trigger on the contract and then sales managers or the enablement team are left to execute and the ask never bubbles to the top. In fact, I’d love to take contracts based on the up-side (we get paid when you improve) and have offered it many times in the past, but the baseline metrics and results weren’t available from the client.
4. Get Leadership Involved (more than they are). How do I know they aren’t very involved? I’ve had about 3 clients out of 300 who were. As a training leader, I had about none. Why is this critical? Because your attendees determine how important the training is based on what the leader says, does, and spends money on. Even if you have to write the script for the VP to kick off the meeting and send over the questions they need to ask in their 1:1 meeting afterward, take the time and do it. Otherwise, you may be the flavor of the month.
Vendor Flipside: They’re my favorite three clients ever. And when they ask for anything extra, they get it. I’ve helped them get jobs 10 years later, spoken free at their conferences, and featured them on our blogs. When a leader lends their time, voice, and stature to training, it will literally change the organization’s culture. Help convince them they’ll get more ROI by being involved. Make it easier on them with cheat sheets and reminders. These clients get double their money’s worth.
5. Focus on Long Term. Ever met with an internal client who wants you to train 5 things in 20 minutes? Me too. Try every single sales leader ever. Here’s why: Most people don’t know the difference between telling and training. That’s why their people don’t change their behavior after being told. Folks, if you want people to change what they’re doing, the training will take 5x longer than you want it to AND the support “tail” for the training will be months, maybe even years. Don’t make training an event – studies show they’ll remember about 30% of what is taught. The best leaders get this fact:
Training isn’t something you did, it’s something you do.
Vendor Flipside: Events are fun. They’re low risk and high reward. We often would have better selling days during training than normal days (live calling during training). Lots of energy, buzz, and results. But if that’s all your vendor is doing, reconsider. What about keeping skills alive? Pulling the buzz forward? Seeing skills move from the classroom to the sales floor? 15 years ago we offered a 1-day post-training follow-up. Then 90 days virtual. Now we do one-year contracts. It’s the right thing to do and the right way to do it. Doesn’t fit the SKO? Hire a speaker instead.
If you’re evaluating sales training, we’re here to help. Fill out the form or email info@factor8.com and let us know how we can help.
Want more information on how to maximize your sales training investment?
Contact us today to request information on our customizable virtual sales training programs available for reps (and managers).
Whether you’re shopping around for external inside sales training vendors or working with your internal training department, knowing what good inside sales rep training looks like is the first step to ensuring your training is checking all the key boxes.
We’ve outlined a few of the most important considerations to keep in mind when choosing an inside sales training partner.
Decide What Good Inside Sales Training Looks Like
This shouldn’t be a surprise to any sales leaders out there — but what makes good inside sales training is results. You’ll be able to know whether or not sales training worked simply because it moved the needle.
These “results” look different depending on your company, team, and goals. It’s important to go into the sales training and decide on what those goals are to you — whether it’s sales units sold or market share gained.
This is even more important when partnering with an external sales training vendor. The vendor should understand your goals as well as your sales process, product, customers, industry, and competitors. There is so much specialization in the market today, don’t let a vendor bring SDR training to your team of AEs.
In order for sales training to be considered “good”, it must achieve your goals. Outlining what these goals are, and what success looks like, beforehand is a surefire way to get what your team needs out of their training.
We recommend identifying metrics, behaviors, KPIs, and overall results that you expect to shift during and after the training. Metrics and behaviors should lift immediately showing you’re on the right track, and KPIs are early indicators that the results are on the way. Identifying metrics or results only can lead to a miss.
Really great sales training is customized to your industry and product/service.
This ensures your reps aren’t left trying to figure out how to take a broad theory and apply it to their job, customer, or service.
While it’s true that customized sales training is more expensive, the ROI is up to twenty-fold when you consider how much your reps are actually retaining, and how much they can apply immediately to their practices.
Use public seminars and events to help someone get a tip or two. Use custom live training to move the needle on results.
2. Get a Professional Sales Trainer
Aberdeen reported that 85% of the sales teams that are considered “best-in-class” utilize professional sales trainers or resources.
Don’t try and turn your managers or reps into trainers. Let’s face it, they’ve got enough on their plates. Plus, even really good managers and reps have no idea how to train — it’s just not their job! They might be excellent at sales, but they have no expertise in training.
Even worse, don’t let your HR department teach sales. They’re great at training and professional facilitation in many areas of your business, but their bailiwick is in company orientation and sexual harassment training — not sales and selling. They may be excellent at training but have no expertise in sales.
See where we’re going with this?
Make sure to bring in someone who is an expert at both training and sales. That’s the secret to good inside sales training, and it’s what the best in class are doing.
3. Make Sure the Training Has the Right Focus
If you’re training your inside sales reps, make sure they’re attending an inside sales training. It sounds simple, but oftentimes well-meaning sales team leaders are duped into thinking “sales training” is enough. Shoe-horning your company’s existing field training for your inside team may actually do more damage than good.
Most popular sales books and training curricula deal with a very narrow view of selling: The conversation between Person A and Person B. Anyone who has been working in inside sales for a while can agree that the true issue lies in getting that interaction in the first place.
If your reps are struggling with connecting with decision-makers, getting callbacks, finding the right people, figuring out who to call, and capturing attention at the top of the funnel, then conversation selling and overcoming objections will miss the mark.
Make sure that your inside sales reps are being coached on topics like:
Leaving compelling voicemails that will be returned
Capturing a prospect’s attention in the first 30 seconds
Leading with value
Creating engaging conversations vs. script reading
How to get a callback or bridge to the next call
Finding more decision-makers in the company
Dealing with gatekeepers
It’s important to make sure other aspects of the strategy are covered as well, so the reps can rely on their managers less for questions such as:
Who should I call first?
How often should I call?
Should I leave a voicemail message?
How often?
Now, what do I do?
4. Sales Training NEEDS to Be Hands-On
Theory stinks.
During the training, make sure reps are getting on the phones. There’s no reason that training shouldn’t be stopped so that the reps can go try out the skills they’re learning, and role-plays don’t really tell the whole story, do they?
Live calls to live customers using the training guarantees that these training methods are going to be applied. Live calling in a safe space leads to more rep buy-in and builds confidence. When reps see the tactics work in real-time they adopt, apply, and try more often. Training fall-off (the forgetting curve) has the odds stacked against it now!
Make the training stick by actually making calls and building pipeline during training.
5. Make Sure Your Managers Get Involved in Sales Training
Put managers in the reps’ training, and when possible make sure they have their own version of the training class tailored for their needs. Managers need to learn how to recognize the new skills in action, when to coach, how to coach the new skill, when to celebrate it working, and how to keep the momentum alive when the trainers leave. Behavior change lives and dies with the management team, and their buy-in, involvement, and use of the new skills are critical to success.
Ask your vendor how the managers will be involved in retaining the new skills.
You got it, training is a process, not an event. Reps reported a “Lack of Development” as a top 5 challenge every year for the past five years as reported by the American Association of Inside Sales Professionals. Aberdeen also reported missing development opportunities as the number one rep-reported reason for leaving companies.
Deciding to invest in rep development is a smart choice, but be sure you don’t assume that it is “one and done.” Your teams want ongoing opportunities to learn, grow, and advance their careers.
Training Magazine reported an average number of development hours/year/employee at about 48 hours – or four hours/month. Is your internal training team ready to provide this? Most corporate training teams get quickly maxed by providing new hire orientation and onboarding. Manager coaching can fill some of the gaps, but if you’re talking with learning vendors, check their ongoing offerings as well.
Ongoing training will often nurture and advance skills taught onsite – helping check the box of retaining new skills and providing the ongoing development reps crave.
The easiest way to accomplish this is with vendor-provided online skills training or inside sales training courses after their session to brush up on their skills, hone in on their weak spots, and keep skills in practice.
When evaluating sales training software, look for interactive resources such as:
Reps want skills on-demand. Learning should be easy, fun, interactive, and flexible. The old days of long-form narrated slides and sales training videos are over. Anyone who has clicked their way through to the final test (or let it run in the background while doing email) can attest to the fact this isn’t engaging or effective.
Again, look for sales training software to engage your management team as well as the learners. New skills and a culture of development live and die on your front lines. Does the software provide manager resources?
How about fast-reference cheat sheets, coaching guides, or contest ideas? Is it nimble enough to allow quick reference before a big call or team meeting?
Get your sales managers involved in testing your top choices.
Are you looking for the best inside sales training programs?
Contact us today to learn about our customizable virtual sales training programs available for reps and managers.
