Top Sales Enablement Challenges: Leaders’ Perspectives

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Quick answer

The biggest sales enablement challenges are usually not about content, tools, or company size. They tend to come from the same deeper issue: enablement is a complex function that has to drive change across multiple teams, levels, and priorities at once.

That is why the most common challenges often cluster around seller engagement, leadership buy-in, strategic positioning, change management, cross-functional alignment, and proving ROI with limited resources. They are connected. For example, if leadership does not see enablement as strategic, it usually stays under-resourced. If it stays under-resourced, it struggles to prove impact. And if it cannot prove impact, it stays reactive.

One useful insight is that these challenges seem remarkably consistent across company sizes and industries. The details vary, but the underlying mechanisms are often the same.

If you are trying to solve enablement challenges, start by looking beyond isolated symptoms. Look at where alignment is weak, where change is not being reinforced, and whether enablement has the authority, clarity, and support to operate strategically.

If you want the full breakdown, the rest of this guide goes deeper.

Introduction

Everyone enjoys a well-conducted sales enablement survey or other forms of research, myself included.

We all appreciate the numbers and graphs that reveal the latest trends, opinions, and statistics. Yet, when you think about it, these often remain just numbers and graphs, making it challenging to uncover the human aspect behind them.

That is why I wanted to do something different for our research into the most common sales enablement challenges across a wide range of industries. 

I wanted to hear real perspectives from leaders in the field.

I was fortunate to get various perspectives from sales enablement VPs, directors and managers (myself included) who run very talented enablement teams at some of the most successful companies in their fields:

• George Campbell – VP of Global Sales Training & Enablement

• Nate Vogel – Vice President, Global Sales Enablement

• Woody Walker – Head of NA Sales Enablement and Digital Sales

• Christian Arrigo – Director of Sales Enablement

• Elena Giunta – Sales Enablement Manager

• Aaron Spencer – Revenue Enablement Director

• Ashton Williams – Director, Strategic Programs (Enablement)

• Ellie Salicetti – Sr Global Revenue Enablement Manager

• Matthew Brown – Sr Sales Enablement Manager

• Chris MacDonald – Director, Sales Optimization

• James Swift – Director of Talent Development

• Jon Foreman – Sales Enablement Manager

• Anish Rajput – Sales Enablement Manager

• Erin Ellsworth – Sr Sales Enablement Manager

• Michelle Curtis – Director, Revenue Enablement

They were willing to share their top challenges, collectively unearthing very fascinating insights – some expected, some less so. 

I believe that, through this approach, I have successfully justified the value of qualitative research and, hopefully, you’ll agree.

Specifically, even when two or three stories from our respondents might be classified as similar (as they often are in large, quantitative surveys), there are countless nuances that render each challenge unique.

Naturally, the responses illuminated specific “themes” that structured this article into distinct sections, each offering a chance to explore the current challenges faced by sales enablement leaders in more detail. 

By the way, make sure to check out my similar, collaborative dissection of sales enablement best practices!

These insights also allowed me to pinpoint a fundamental trait of sales enablement, identifiable as the root cause of most challenges I will explore today: the intricate nature of enablement as a discipline.

What makes sales enablement very complex?

As highlighted in the introduction, the bulk of challenges shared by my respondents can ultimately be linked, upon closer examination, to one of its defining features: its inherent complexity. 

This complexity stems from two primary factors: sales enablement’s status as a relatively new discipline and the demanding nature of enabling sales, which is further intensified by the need for intricate interdepartmental collaboration. 

Relatively recent nascence 

Sales enablement is arguably the most recent discipline to enter the go-to-market ecosystem and show its worth both quantitatively and qualitatively. 

Yet, like any emerging field, it experiences common growing pains: widespread misconceptions, resistance to adoption (both overt and subtle), dismissal as just another fleeting trend, a lack of industry standards, and more. 

These issues seldom occur in isolation, and their interrelated nature complicates their resolution.

For instance, common misunderstandings about sales enablement can lead to it being dismissed as little more than a buzzword by senior business leaders.

This perception can create a significant barrier to its adoption, stemming from resistance at the highest levels.

Navigating vertical alignment and horizontal collaboration 

That being said, even if sales enablement had been around since the Iron Age, it would still have to entail the need to move effortlessly and effectively both along the company’s vertical hierarchy and horizontal diversity. 

When discussing the hierarchy vertical, without true leadership (often C-level) support, enablement efforts will most often end up being fractional, too narrowly focused, temporary, and reactive.

At the lower rungs of the hierarchy, enablement professionals need to understand what the sales reps on the front lines are experiencing and how they can be supported most impactfully.

In the middle, there are the often-neglected sales managers whose involvement is actually essential. 

Shifting the focus to the horizontal dimension, enablement professionals, and leaders in particular, need to be the primary motivators in bringing together the go-to-market departments such as marketing, product, customer success, and , of course, sales. 

All of these departments come with their own goals, agendas, targets, deadlines, problems, and internal politics that form an organisation-wide layer of eggshells that enablement professionals need to walk on and avoid making costly sales enablement mistakes. 

On top of all that, all of these units have their individual, departmental verticals that also have to be taken into consideration, making stakeholder management in enablement a profusely complex matter. 

A million little reasons

It’s important to keep in mind that these two main reasons for complexity are just the tip of the iceberg.

There are many smaller factors at play, each adding to the complexity. 

Moreover, when these smaller factors interact with one another, they amplify the complexity even further.

The unexpectedly low impact of certain factors

The previous section may have felt too theoretical to some, but from this point forward, it will become clear why I investigated this innate complexity of sales enablement.

Namely, as I was going through the responses sent by these incredible sales enablement leaders, certain “themes”, or types, arose.

Upon closer analysis, I came to the conclusion that the underlying causes for most types of challenges could be categorised under one of the two factors above (often both). 

Moreover, some of the factors I expected to be absolutely vital turned out not to be.

This challenged many of my preconceptions.

For example, I discovered that the size of the company played a surprisingly minor role when it came to the types of sales enablement challenges my respondents encountered.

A head of enablement and digital sales at a consultancy behemoth of over 10,000 people shared very similar challenges as a senior global revenue enablement manager at a company of 100 and a revenue enablement director at a company of 2,500. 

Of course, the ways in which these challenges manifest themselves are different, but the underlying mechanism is the same. 

This trend is evident across the board, with challenges being strikingly similar in large companies that have thousands of employees and well-established enablement teams to those in much smaller companies with tiny sales enablement teams. 

And I really tried to cover companies of different sizes:

• Small – up to 250 employees

• Medium – between 250 and 2,500 employees

• Large – 2,500 employees and above

Similarly, the industry in which the respondents worked also seemed to play a relatively minor role.

Admittedly, they all mostly worked in the digital arena, but still, the exact fields and the nature of their products/services varied greatly:

• Digital, cloud and advisory services

• Health and security risk services

• Business software 

• Media & events 

• Cybersecurity

• AI-based products and services

Despite this, I couldn’t identify any industry-specific patterns or trends that would be noteworthy, which, paradoxically, made it noteworthy.

Having said that, it’s also important to highlight that the challenges gathered in this study are only the 3 most pressing ones for each of my respondents, and there is always a possibility that certain size-dependent or industry-specific trends would have emerged in more in-depth conversations and with a larger volume of responses.

Right now, however, the only common-sense conclusion is that the majority of challenges that sales enablement leaders encounter are significantly influenced by the function’s complex nature.

Let’s now get deeper into the core of this work, exploring the various themes and what the sales enablement leaders had to say.

Investigating the sales enablement challenges

As I start this deep dive into the challenges, I should inform you that I included the perspectives of 16 sales enablement leaders who shared the three most pressing obstacles they are facing. Two respondents shared 4, which neatly brought the number to 50 in total.

I categorised these 50 challenges into 8 different themes, as illustrated in the image below. 

Let’s go through each one of them.

Sales team empowerment and alignment 

The initial theme identified among the diverse sales enablement challenges centres on “sales team empowerment and alignment.”

This encompasses key areas such as engaging sales reps, securing their buy-in, providing effective sales training, and standardising sales processes and methodologies

A number of the respondents mentioned the lack of or inconsistent training, sales processes, and sales methodologies as one of their top challenges. 

For example,  Christian Arrigo, the director of sales enablement at a US-based cybersecurity company, mentioned the following as one of his top challenges:

“There isn’t any standard methodology, so it’s important we lay that foundation so we can speak a common language and measure what good looks like.

I am in the process of bringing in an outside vendor to help train and accelerate the process.” 

Elena Giunta, a sales enablement manager at a large Canadian media company, mentioned inconsistent processes as one of her main challenges:

“Inconsistency in the sales process can lead to confusion among sales reps and impact the overall customer experience.

Standardizing and documenting processes can help maintain consistency.”

She pinpointed the lack of sales training as another challenge she was facing:

“Inadequate training can hinder the sales team’s ability to use new tools and technologies effectively. A lack of understanding about products, services, or sales techniques can also impact their performance.”

Nate Vogel, the VP of global sales enablement at one of the world’s largest data and AI companies, shared his unique challenge where their sales enablement initiatives need to be extended to partner enablement too:

“One of the most important key areas to hit is having your partners enabled just as much as the field is internally. At our company we believe in a philosophy of +Partners to make sure that if we roll out something key to our sales team, we should also train our partners.”

Aaron Spencer, the revenue enablement director at a 2,500-person business software and services company, was almost laconic about her top salespeople-related challenge:

“Identifying & prioritising the skill needs of sellers to ensure they achieve quota.”

Ashton Williams, the director of strategic enablement programs at the company behind a popular messaging platform, mentioned one very specific area of sellers’ skills development that she finds challenging – selling in competitive scenarios:

“Nailing competitive with sellers.

Companies usually focus on intel when we think of competitive but the skillset of having thoughtful conversations with target audience that involve competitors is one that most sellers struggle with.

The mention of a competitor can create fear and erode seller confidence, and it requires constant practice to manage these interactions in a way that builds trust, demonstrates domain expertise, and collects critical information to close the deal.”

Ellie Salicetti, a senior global revenue enablement manager at a UK-based cybersecurity company, emphasised the importance of good communication within the sales organisation:

“In the fast-evolving startup and SaaS landscape, aligning diverse stakeholders is a pivotal challenge.

The key lies in bridging different visions and strategies, ensuring everyone from top management to the sales floor is moving in unison.

Clear, transparent communication and setting common goals are essential to turn these varied perspectives into a cohesive sales enablement strategy.”

The most common salesperson-related challenge, however, turned out to be sales personnel engagement and buy-in. 

Chris MacDonald, the director of sales optimisation at a large UK-based events company, provided crucial insight by taking the viewpoint of an average salesperson:

“Identifying how operational procedures impact revenue for sales reps can be a challenge.

As an individual sales contributor, you have your methods that work for you. Changing these methods based on organizational procedures and company goals can be a difficult hurdle to overcome. 

Why should I make this change? Why should I do more admin work (perceived)? How is it going to help me sell more?

These are common, and justifiable reactions from salespeople when flipping the script on operational procedure.

It is especially difficult to ‘sell’ a salesperson on doing something new or challenging for the greater good of the organization when there may not be, or easily seen, direct benefit in the short term.”

Matthew Brown, a senior sales enablement manager at a leading global health and security risk services company, also mentioned this as one of the challenges:

“Having sellers understand the improvement (value) that the activity/change will make to their every day”.

Woody Walker, the head of NA sales enablement and digital sales at one of the world’s premier digital, cloud and advisory services companies, shared the following:

“Ensuring we are supporting our sellers to keep them engaged.

I’m seeing a lot of burnout because it’s been so hard to sell the last two years, so I’ve been thinking about what I can do to lift them up and provide them with more fun activities and training time to make them feel more appreciated and reduce the drag that I’ve been seeing in sellers over the last two years.”

George Campbell, the VP of global sales training & enablement at a US-based cybersecurity company, elaborated on salespeople’s engagement in the following manner:

“Seller engagement.

This is especially tough, given how many parameter departments are demanding time from sellers, and expecting them to behold a plethora of knowledge across many disciplines.

Over the last 25 years, I’ve actually come full circle and recently observed the massive benefit of very early on, conducting in-person workshops that focus on personal development habits. 

Avoid the promise of bulletproof playbooks or value props, and instead get everyone in a room for good old-fashioned time together, flipcharts & sticky notes, and most importantly, to hear from individual sales reps… the actual people who have to grind their way through the quarter.

This relationship-building is mutually beneficial.

It allows sellers to ‘vent’ a little, but allows the enablement leader to position all future initiatives as genuine care & well-being, as opposed to a routine, stick-beating activity.  

Recently, I’ve found incredible results in connecting the person to the process by facilitating team building, team discussion, debate, and ultimately, establishing realism in the art of the possible.

Furthermore, establishing a fair expectation that teaching best practices should not make them feel like they must gain mastery overnight…help sellers to understand that you defend their permission to get good at a reasonable pace.”

George also mentioned pride and ego as one of the impediments in this area:

“To be clear, this rarely comes from a bad place.

It’s a human symptom of self-preservation, quite often because of poor support from management to create a safe environment that includes permission to fail (caveat: whilst trying one’s best). 

It can significantly impede progress because sellers will hide behind what they are comfortable with, and saturate the enablement leader with a plethora of reasons – usually with confusing tech-talk – why they cannot learn or apply best practices. 

I’ve found success in being incredibly sincere in offering that safe space… making it clear that poor effort is absolutely something that should be managed accordingly, but that lack of knowledge or skill should be supported, and that all sellers should feel confident that they will be greeted with support should they put their hand in the air and say ‘I don’t know’.

I’ve found myself going further by candidly advising that if there is an authentic ask for support (coupled with a commitment to improvement), then any environment that does not allow this should be revised as to whether or not it’s a place to develop one’s career. 

Personally, I’ve found that reinforcement of the message ‘it’s OK not to have all the answers, especially as a seasoned seller’, and that embracing development opportunities will reap rewards accordingly.”

Leadership alignment and buy-in

In the preceding section, I highlighted how crucial engagement and buy-in are from the sales team. Yet, these elements are possibly even more critical at the senior levels of a company. 

Leadership endorsement, especially from C-level and VP-level executives, often emerges as a pivotal factor in an organisation’s genuine commitment to sales enablement initiatives. 

Typically, the push for adopting and executing certain sales enablement strategies is initiated by someone in a leadership role.

However, having a high-level advocate doesn’t necessarily ensure unanimous support from the rest of the leadership team.

Often, due to the inherent pressures associated with their roles, they might view sales enablement as an inconvenience or even as a financial drain.

George Campbell, who provided the perfect segue into this section, added this on the subject of genuine leadership buy-in:

“It is common to gain easy agreement with the broader GTM leadership team members, but when it comes time to execute the “embedment” phase, that’s when all the questions arise – including objections to the process. 

I’ve found that it helps to agree on a very comfortable timeline for embedment.

This means avoiding commitment to significant result changes, but being clear that the value of enablement is to get the sales team “in the zone” for continuous learning.

Pushing too hard will result in disenfranchisement and impact future projects.”

Ashton Williams referred to it as executive alignment:

“Executive Alignment – with the shifts in the economy and buying behaviour, we’re seeing many changes across our executive teams and energy around all the things the field needs to know.

Getting execs aligned to what we can do well while changes are happening can be challenging.”

A critical yet frequently overlooked tier in sales enablement is the managerial level, particularly sales managers and front-line leaders.

For various reasons, many enablement programmes concentrate exclusively on sales representatives, their skills, knowledge, and processes, without adequately recognising the essential role of sales management support and buy-in. 

Matthew Brown explicitly mentioned, “Getting buy-in from front-line sales leadership to drive the change with their teams”, as a crucial challenge to overcome.

I go in-depth about this in my article on sales training best practices, where I explore the reasons behind its critical importance.

Positioning sales enablement as a strategic function

Without steady leadership support, establishing sales enablement as a strategic discipline proves challenging.

Although enablement operates on both tactical and strategic levels, its effectiveness is maximised when recognised as a strategic partner within the organisation, functioning as an independent business unit.

Jon Foreman, a sales enablement manager at a Canada-based HR and management software company, puts this very succinctly:

“Enablement as a relatively new function typically grows out of Marketing, Sales, Operations, or some other established part of the revenue organization. 

Depending on where that is, Enablement gets pulled in different directions which doesn’t necessarily set it up to succeed. 

Enablement needs its own place where it can function independently of, but in closer partnership with, Marketing, Sales and Operations.”

Jon also mentioned how the sales enablement’s lack of strategic status impedes the crucial collaboration – the one between enablement and sales leadership:

“I believe that Enablement has a critical position as a strategic partner to sales leadership, and not just as a support team that helps to execute plans.

Sales Leadership is intentionally focused on their current reality, and truth be told, don’t get a lot of time to focus on process improvement, future-proofing, large-scale upskilling, etc. 

Enablement can be the progressive leader in those areas, so sales can focus on last-mile implementation and revenue generation.

In reality, sales leadership and enablement are working in parallel to the detriment of both sides’ plans.”

James Swift, the UK director of talent development at an international consultancy company, states that becoming strategic also means setting limits to what sales enablement is supposed to do:

“Knowing where to draw the line.

Defining what sales enablement won’t do is just as important as defining what it will do.

How will you support learners, how will you support their managers, how will you support their senior stakeholders?”

Michelle Curtis, the director of revenue enablement at a digital credential management software company, shared a similar sentiment about sales enablement having to establish itself as a unique business function:

“The requirement for enablement to conform to the needs of the business they serve.

Enablement’s roles and responsibilities shift depending upon the business- at one company, you can be mainly focused on training; at another, content and positioning; at another, data analysis and reporting. 

This can be really difficult for those in enablement, especially those who know good enablement is comprised of all of those things under a single strategy. 

However, if you don’t have a leader who understands that, or has experienced poor enablement, you are destined for reactive enablement.”

Michelle’s emphasis on shifting from reactive to strategic, proactive enablement mirrors a major challenge identified by Aaron Spencer as one of her top three:

“Transitioning from being a reactive revenue enablement team to becoming a more strategic partner.” 

Achieving a balance between tactical, short-term goals and strategic, long-term objectives in sales enablement presents a significant challenge for smaller companies and their compact enablement teams. 

Christian Arrigo, as a one-man sales enablement team, told me what one of his biggest challenges is:

“Trying to prioritize where I spend my time as a single revenue enabler, how to make the biggest impact but not spread myself too thin.

Balancing tactical and strategic enablement; this is a new concept for my company, and we also have a new CRO, so it’s about aligning with his plan and strategy”.

I myself have experienced similar situations, trying to balance short-term impact with long-term enablement for sustainable revenue growth.

This challenge is mostly prominent when you find yourself joining an organisation with no sales enablement function, where your task is building the function from scratch. 

In such a scenario, you have to come in and demonstrate the impact of some enablement initiatives in the short term to help gather resources to scale programmes and fulfil a long-term plan. 

Sales is inherently a field with a constant short-term need to hit quota and add revenue, so if you aren’t careful, you can easily lose track of the long-term vision and find yourself reacting rather than working towards building a strategic function. 

Enabling and managing change in the sales organisation 

Once a sales enablement team finally earns its rightful place at the strategy table, one of the first things they notice is that change is easier to instigate and maintain.

However, even then, the sheer amount of change can make managing it the biggest challenge of them all. 

As Matthew Brown puts it:

“For me, the key challenges are all grounded in change management. 

Almost everything we seek to do is about change, whether that be about helping a buyer, a seller, a sales leader, or others change something…their opinion, their desire to implement change, their process, their actions, whatever!”

He goes on to say:

“In spite of our organisation forever changing, it requires an enormous amount of effort to trigger it! (generating a need for change within senior management, and other relevant departments…finance, etc.)”

Michelle Curtis also mentioned change management as one of her top challenges:

“Now more than ever, we’re seeing reductions in force, leadership changes, and tightening of pursestrings. 

Managing this can be very difficult for enablement, especially when there is a push from leadership to make many changes at once. 

Sales can’t handle that much change at a time, especially now that more and more sellers are missing their quotas.”

Anish Rajput, a sales enablement manager at a UK-based AI video generation platform, conveyed this challenge from a more mindset-related angle:

“Enablement is about changing a seller’s mindset, which is one of the most difficult things to do, not just for sellers but for everyone. But those who adopt a customer mindset, a value-driven mindset, and even a learning mindset, will be incredibly successful.”

On the other hand, James Swift was more detail-oriented when talking about his change-related challenges:

“Cutting through complexity:

• Continuous improvement means constantly reviewing processes to improve performance. Being brave enough to tear down something you’ve built with sweat and tears, and starting again rather than just adding on top of existing infrastructure is difficult but necessary. Too often, I see people trying to cling to things they’ve built, which just leads to overcomplication.

• Road test everything – Just because you’ve built it doesn’t mean it’s useful.”

Erin Ellsworth, a senior manager of sales enablement at a leading global data & AI company, addressed the constant need for change as a significant challenge:

“Like many businesses, perpetual changes are the norm at my company. Navigating this fluid environment poses a challenge for sales enablement as we strive to ensure that all sales material remains not just current but highly relevant.”

Ellie Salicetti even introduced change fatigue as a challenge she has to keep her eye on:

”Rapid product updates and market shifts are common in this sector, making change management crucial yet challenging.

The sales teams must be agile, adapting to these changes without losing momentum.

This requires not just training but also a culture of continuous learning and flexibility, where change is seen as an opportunity rather than a hurdle.


In an environment where change is constant, change fatigue becomes a real concern.

Sales teams might struggle to keep up, leading to decreased morale and productivity.

Addressing this involves balancing the pace of change with adequate support and recognition, ensuring the team remains motivated and engaged amidst the flux.

Regular check-ins and feedback sessions can be instrumental in mitigating this fatigue.”

Cross-functional collaboration and alignment 

Initiated changes within sales and marketing departments extend beyond their own scope, impacting other go-to-market (GTM) teams as well.

Ensuring that all departments are aligned and their input is considered presents a challenge, as highlighted by some of the contributors.

Elena Giunta painted a clear picture of what happens when this challenge isn’t tackled head-on:

“Communication breakdowns between different departments, such as sales, marketing, and customer support, can lead to misunderstandings, conflicting strategies, and a lack of cohesion in the overall sales enablement process.”

Erin Ellsworth emphasised the importance of a sales-centric outcome of interdepartmental collaboration:

“Sales enablement must collaborate with diverse cross-functional partners to support our sales team. However, this collaborative motion often involves juggling competing priorities. Striking the right balance between managing the expectations of various teams and maintaining a sales-centric outcome proves to be a demanding task for sales enablement.”

Jon Foreman illustrated what the result is when the enablement team is not brought into the loop as soon as possible:

“New processes, programs, and projects that ultimately will involve enablement efforts don’t include enablement from the start. 

Marketing builds new marketing materials to serve as lead generation, and sales builds a new process for handling those leads, but only after those pieces are put into place do they involve enablement to bring the teams up to speed.

This creates a huge lag in terms of process readiness and team readiness that can break seller confidence in the sales org.”

I have to admit that enabling cross-functional collaboration across GTM is one of the biggest challenges for me as well.

True sales acceleration happens only when sales enablement is able to leverage the collective knowledge and expertise of the GTM organisation.  

In a remote environment, this challenge intensifies due to the need for extensive communication across different departments, along with the establishment of shared goals and expectations.

Managing these components alongside any programme becomes particularly taxing when enablement operates with limited resources.

If you want to read more on this subject, I’d recommend my articles (done in collaboration with enablement leaders from around the world) on stakeholder management mistakes and best practices.

Limited resources and demonstrating ROI

Initially, I planned to treat the themes of limited resources and demonstrating sales enablement’s value as distinct topics.

However, upon reflection, I recognised they’re intertwined in a classic “chicken or the egg” dilemma. 

Demonstrating the tangible ROI of enablement is essential for securing additional resources, or sometimes even the most basic ones.

Yet, the question arises: “How can a department prove its worth without having the necessary resources to operate effectively?”

George Campbell had a similar thought when he shared underinvestment as one of the top challenges:

“This is a big one.

In recent years I’ve seen a pattern of behaviours from GTM leaders who have become ‘awakened’ to the stats around enablement, fundamentally showing a clear & direct ROI on sales performance. 

The upside is that there is a firm commitment to an enablement investment.

The downside is that there is a ‘silver bullet’ miscomprehension, and the investment gets limited to one (or very few) enablement personnel, meaning that enablement functions are created without the resources to be effective. 

Understandably, there can be a basic face-off of ‘I should hire an AE who actually sells, instead of investing more in enablement’. 

Of course, it doesn’t take a genius to work out that investing in more enablement is a force multiplier across ALL the sales function, and that making all sellers more effective is worth more than not, at the expense of a single patch. 

What’s the solution? 

Well, it’s very tough…short of the stars aligning to produce clear evidence of mass impact on the number, then it’s a patience game, coupled with firm education to the CRO & their team.

Of course, using nomenclature that aligns with sales/results, goes a very long way.”

Chris McDonald also noticed this chicken-or-the-egg conundrum when he told us that proving enablement works was a top challenge for him too:

“Showing the impact of enablement strategy and programs and building a case for more resources is always a challenge. 

We are, in many respects, the unsung heroes of sales and operations.

Our role is to support and align teams to drive more and retain revenue.

There are so many aspects that go into that last sentence, identifying the pre- and post-metrics that your enablement program has improved is so critical. 

I would encourage any enablement professional starting a new role to identify the baseline metrics they plan to impact within the first 30 days of starting their new role.

This will help you move mountains when proving how impactful your program has been with hard data.”

Nate Vogel was also very explicit about how important demonstrating the ROI of sales enablement is for him.

Moreover, he was kind enough to provide a lot of advice on the issue:

“First and most important challenge is: How do you measure with valuable data to showcase to your C-suite or board the effectiveness (or ineffectiveness) of Enablement?

This is one of the hardest things to do in our job, but also something we are getting closer to showcasing.

Even if the training was rated highly but you see the adoption metrics are not picking up – key executives appreciate that you lead with data (good or bad). 

How do you start?

a. You can, of course, do standard leading indicators like CSAT (how well did your sales team rate after the training session). 

b. How much content was shared after the training, where standard CMS (Content Management System like Highspot or Seismic) will show the data of what was shared with customers, usually in a micro-site. 

c. The most important is to show adoption metrics using a conversational intelligence tool like Gong, where you can set up in advance Smart Trackers for key training words or slides that sellers use, like rolling out a new messaging playbook where you can see an increase in win rates or decrease in churn.

Or, to my earlier point, if the data is not showing adoption, you can at least know and either reinforce another training or change direction. 

This is one of the key light bulbs that I am making sure we are using here at our company; it’s  about being data-driven to not only show training scores but training results.”

Anish Rajput also acknowledged some improvement on this matter, but still picked showcasing value as one of his top three challenges:

“It has been difficult to attribute revenue to enablement programs; this is slowly improving with more data and tools, but is still a challenge at times to attribute the dollar value to enablement.”

Michelle Curtis adeptly added that the typically delayed indicators of sales enablement’s effectiveness play a significant role:

“Proving value – this is always a challenge in enablement, as most of our indicators are lagging.

There is no way for us to show that our specific actions directly impacted a specific metric.

For example, our training initiative directly caused conversion rates to increase.

This is definitely a handicap for us, as our value is often determined by those types of metrics, especially if enablement reports to sales.“

Others zoomed in on the resource-related challenges. 

Erin Ellsworth, for example, shared the following as one of her top challenges:

“Advocating for essential resources: the core of our role is to enable the sales team to capture more revenue.

Yet, the uphill battle of securing necessary resources is a common struggle for sales enablement professionals.

Whether it’s securing additional headcount, acquiring essential tools, or negotiating internal bandwidth, the challenge of being under-resourced makes gaining approval for a business case a common struggle.” 

Ashton Williams agreed:

“Resourcing – most teams are still learning to work lean and wear many hats, even at the biggest organizations.

Retaining top talent and resourcing accordingly when the demand for enablement is skyrocketing internally is critical this year.”

Evolving and scaling sales enablement 

Some sales enablement teams are fortunate enough to have solved, one way or another, the whole chicken or the egg situation. For them, the challenges include taking their efforts to the next level. 

Nate Vogel, for example, is encountering the challenge of scaling enablement at his company:

“Another main challenge is how to do you scale enablement? 

a. Manager Enablement is the next big thing in our space. What I have done in the past is too much enablement-to-rep.

What I (and our Enablement team) should do more is enablement-to-manager and then manager-to-rep to showcase reinforcement and modelling the right behaviour. 

b. When you roll out a new methodology or competitive training, one of the best ways I have seen adoption increase (usually at least ~25%) is when the senior sales leader or CRO models the training themselves first in front of the entire sales team.

When the leaders show this by modelling then you show the importance to the field; when your most senior sales leaders have taken the time to master the content, you know it’s important.”

For Woody Walker, it’s about moving from sales to buyer enablement:

“Focusing on buyer enablement and not just sales enablement.

Differentiating from the competition by creating unique and compelling content, leveraging data and analytics to personalize the customer journey as they do in retail and ensuring my sellers are trained on buyer empathy and how to help target audience buy.”

For me, one of the biggest challenges with scaling sales enablement teams has been finding the best talent. 

Sales enablement hasn’t been around for long.

It’s a relatively new discipline, so it’s difficult to find professionals who can combine an understanding of sales with strategic thinking, project management, and learning and development skills. 

In addition, they require great interpersonal skills, including charisma and persuasiveness, to gain credibility and buy-in quickly.

This mix of strategy, communication, project management, learning and development, and technical skills isn’t easy to find.

Tools, data, and AI

Why save technology-related challenges for last?

Well, for one, only a few respondents identified technology as one of their top three challenges.

Moreover, these days, we have access to all the technology we could possibly need, so the capabilities of sales enablement software often aren’t the problem.

It’s more about getting people to adapt and embrace change.

Chris McDonald had the most to share about his technology-related challenge:

“Outreach, Gong, Salesloft, etc… Determining the best sales enablement tools for your team is critical to solving the gap in your sales strategy.

More importantly, regardless of the tool chosen, you need the team to adopt and use it.

This is a challenge from multiple perspectives, such as technological acumen, trust in execution and content, and overall change management.

A strategy I have always used in enablement is to not implement or ask my team to do anything that I’m not willing to do myself.

I lead by example and work to become an expert on every tool. Having a trusted colleague who can relate to the role of the sales rep is critical in driving adoption.”

Woody Walker, James Smith, and Anish Rajput focused more on AI in particular. 

Woody actually put it at the very top of the challenges she is experiencing:

“I think my first one is encouraging AI and managing the impact of Al on the sales process.

The implementation of Al in sales can help sales teams automate tasks, optimize workflows, personalize interactions, and generate insights from data; one of my top focus is to reduce the admin burden so they can focus on spending time with the client and not forecasting, documenting opps, and notes.“

James suggested that AI might be the sales enablement solution for standardising data:

“Data should be standard, what insights can you provide to the organisation to help stakeholders make better decisions?

This is where AI can play a key role.”

Anish voiced his concern about using AI the right way:

“AI brings as many challenges as it does solutions. How do we ensure that teams are using AI to expand on their existing skills, and automate admin, rather than asking ChatGPT to create a cold email for a certain persona?”

Differences and similarities with larger-scale research 

While reviewing the feedback from sales enablement leaders, several observations stood out to me, and likely to you as well.

Some findings aligned with my expectations, while others were quite surprising.

Specifically, for those who are seasoned enablement professionals and have been following the stream of quantitative research published in recent years, you might have recognised that the challenges our respondents mentioned don’t entirely align with the recurring statistics from those larger-sample studies.

One of the most striking inconsistencies concerns the topic of sales enablement content.

This issue tends to be a constant in most enablement surveys and research.

Take, for instance, the Sales Enablement Collective’s (SEC) 2022 Sales Enablement Landscape survey, which identified subpar content quality as the second-most cited challenge by participants.

In contrast, sales enablement assets were hardly a blip on the radar in my survey.

It was only brought up by Ashton Williams, and even then, it was in relation to a specific context.

Additionally, you might have picked up on the absence of change management as a significant challenge in the SEC’s findings, whereas it was a prevalent theme in my own research.

My results also showed a stark contrast to the figures from the Sales Enablement PRO’s 2022-2023 Sales Enablement Analytics Report.

Demonstrating the ROI of sales enablement emerged as a commonly cited challenge among our survey participants.

Conversely, the SalesEnablementPRO’s report indicated that an overwhelming 84% of their respondents felt at least somewhat confident in their ability to prove the impact of their enablement efforts.

However, my findings do converge with those of quantitative studies in several areas.

For instance, the theme of inadequate resources, both in terms of personnel and budgeting, frequently crops up.

Similarly, securing buy-in across the organisation, from various departments to the sales hierarchy (ranging from directors to individual representatives), stands as a shared challenge.

The discrepancies between my findings and those of broader quantitative studies might stem from several factors. 

Firstly, our research did not encompass as large a sample, which could influence the diversity and range of responses captured. 

Additionally, the format of many large-scale surveys, with their predefined response options, may not fully encapsulate the breadth of challenges that enablement professionals face. This limitation contrasts with open-ended queries, which can unveil a wider variety of insights.

It’s also critical to consider that some of this research might be conducted by entities with vested interests, potentially biasing outcomes to favour certain narratives or solutions.

Such sponsorship can subtly steer results, crafting perceptions that align with the sponsor’s objectives rather than the objective realities of the sales enablement field.

Given these considerations, my commitment has been to uphold the highest standards of objectivity in this research, trying to portray an undistorted view of the enablement landscape. 

These findings should serve as a reliable resource for professionals seeking to navigate the complexities of sales enablement with clarity and integrity.

Conclusion

One of the primary objectives of this research and the subsequent article was to investigate the unique complexities of sales enablement as a field through the perspectives of those leading the charge. 

Thanks to the incredible willingness and vast experience of our contributors, I have been able to provide a glimpse into the intricate world of enablement, beyond just data and statistics.

As I examined the responses more closely, it became apparent that many of the challenges faced by enablement leaders are rooted in the industry’s relative novelty within the GTM ecosystem.

This, combined with the necessity for cross-departmental collaboration and engagement across various levels, places these challenges at a strategic level.

Regardless of differences in company size or sector, the challenges outlined by leaders in the field are remarkably consistent, highlighting a common “battle” within the discipline.

Several key themes have emerged, notably the significance of empowering marketing and sales teams, obtaining leadership buy-in, and the strategic placement of sales enablement within organisations.

While the topic of this article may lean towards the pessimistic, and while it’s clear sales enablement leaders still face serious obstacles, the overarching sentiment from every response hints at an ongoing journey of progress and innovation.

Check out this article for some sales enablement ideas!

It seems that each challenge also presents an opportunity for innovation and growth, at least in the eyes of the experts who participated in this study. 

Sales enablement is a discipline that continues to evolve and strengthen with each passing day.

The responsibility falls on us, the individuals within the enablement community, to foster this development.