Sales Team Challenges and Skill Gaps [Research Report]
Sales Team Challenges and Skill Gaps
[Research Report]
[Research Report]
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.
DOWNLOAD: Sales Training Vendor Partner Checklist
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:
In reality, this creates three big problems.
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.”
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.
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.
If you run enablement or revenue, you are caught in a familiar trap.
But you also run into the reality:
But the tradeoffs are real:
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.
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:
For revenue leaders, inside sales training that is truly customized means:
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.
DOWNLOAD: What Best-in-Class Sales Training Looks Like Checklist
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.
So we created the All Access Sales Training License.
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:
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.
Contact us today to learn about our customizable virtual sales training programs
available for reps (and managers).
[Video Recording]
[Research Report]
[Guide]
[Checklist]
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.
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:
Consistency is what turns momentum into real, scalable growth. And it starts at the manager level.
Give them the tools to:
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.”

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.
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.
Because a manager who builds skill, confidence, and trust is someone who retains reps, not replaces them.
READ: Build Your Sales Manager Cadence (& Save Time and Stress)
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:
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.
READ: The Best Sales Coaching Questions Ever
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.
[Video Recording]