When and How to Build a Sales Enablement Function – Experts’ Opinions

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.

Introduction

Whenever I talk to sales or revenue leaders, company founders, or CEOs, one question almost always comes up:

When is the right time to build a sales enablement function?

That is, of course, if their company hasn’t already started building one.

I’ve also heard from many colleagues in enablement that this is a question they frequently encounter.

Closely tied to the when is the question of how to build a sales enablement function.

This question doesn’t just come from revenue leaders or founders but also from fellow enablers. Often, they’re professionals tasked with building the function for the first time in their careers – usually as they advance and are brought into startups or smaller companies to take on this challenge.

Getting it wrong – whether it’s the timing or the execution – makes it nearly impossible to create an enablement function that is strategic, effective, and impactful.

Worse, starting off on the wrong foot doesn’t just waste resources for that one company; it also damages the entire discipline. Word spreads quickly, and before long, sales enablement gets unfairly labeled as a money pit that yields no noticeable results.

In other words, the stakes are high.

Fortunately, the enablement community has been more than willing to share their expertise, experience, and insights to help me tackle these two critical questions. 

We’ll soon dive dive into the heart of the matter – understanding when and how to build a sales enablement function – but before we get started, I’d like to introduce the incredible contributors who made this exploration possible.

About the contributors

The enablement community truly stepped up, with 17 incredible individuals generously taking time out of their busy schedules to share their insights on the ever-challenging task of building an enablement function.

The contributors are all senior enablement leaders at their companies, and they have held some of their previous sales enablement roles at companies such as Amazon, Salesforce, Hewlett Packard, Dell Technologies, Slack, Oracle, LinkedIn, Sprinklr, and Gong, just to name a few. 

Nearly all of them have firsthand experience building enablement functions from the ground up or were actively involved in the early stages of doing so at their companies. Some contributors, in fact, are currently doing this at this very moment, meaning they are living and navigating the answers they shared.

Our 17 contributors are:

D’Andre Crump – VP of Revenue Enablement

Dick Dunkel – VP of Field Enablement

Gary Manalus – VP of Revenue Enablement

George Campbell – Former VP of Enablement, Managing Director & Founder

Jill Guardia – Senior VP of Revenue Enablement & Operations

Jocelle Sarenpa – Sales Leader & GTM Strategist

Kunal Pandya – VP of Global Revenue Enablement

Lisa Duncan – Senior Director of Revenue Enablement

Mark Siciliano – Former VP of Enablement, Strategic GTM Advisor

Nate Vogel – VP of Global Sales & Partner Enablement

Robert Read – Head of Revenue Enablement

Ross McLean – VP of Revenue Strategy & Enablement

Samantha Thompson – Head of Revenue Enablement & Enablement Consultant

Sheevaun Thatcher – Former VP of Enablement, Strategic GTM Advisor

Timea Bara – VP of GTM Enablement

Tom Greenwood – Sr. Sales Enablement Manager

Trafford Judd – Senior Director of Revenue Enablement & Operations

I’ve published many collaborative articles here at The Enablement Insight, but as I read through this one, I couldn’t shake the feeling that this topic held a special significance for the contributors – just as it does for me. 

When is the right time to build a sales enablement function?

Given that this entire article aims to address two main questions about building a sales enablement function – the when and the how – it’s only natural that the first question I posed to our contributors focused on timing.

I wanted to understand how enablement leaders – many of whom have built the function from the ground up (and some who are actively doing so right now) – determine the right moment to start.

Their diverse responses highlighted just how intricate the field of enablement is, revealing the countless factors that must be considered before even beginning to answer this question.

Is it just about the number of reps?

As expected, some contributors mentioned specific headcounts of customer-facing personnel in their responses, but it would be a mistake to view these numbers as automatic triggers for building an enablement function.

For example, Robert Read, the Head of Revenue Enablement at a leading business planning platform, highlights that the “need arises” for a fully dedicated enablement function at around 70-80 reps.

However, he points out that three additional factors are far more important in guiding this decision:

• Critical mass: Reaching a size where the investment in enablement makes economic sense.

• Product complexity: Simpler products or services may require less enablement support.

• Emerging silos: As silos creep into a growing business, so do disparate ideas and approaches. This can result in fragmentation across teams and hinder alignment, creating a clear need for unification.

Similarly, Kunal Pandya, the VP of Global Revenue Enablement at a leading trademark and brand & content protection solutions, suggests starting to build the function when the sales team transitions from being “a small, closely-knit group.”

He estimates this at around 8 reps, but his key point is that beyond this size, it becomes increasingly difficult to deliver consistent learning, coaching, onboarding, support, and content – regardless of the precise headcount.

Other contributors cited numbers such as 20 customer-facing roles, 40-50 reps, or even 10-15, depending on the context.

However, none of these numbers should be taken as definitive thresholds.

Instead, they reflect the contributors’ experiences and the broader conditions surrounding their companies at the time.

In other words, it’s not just about the number of sales reps but about what those numbers represent in terms of organisational complexity, growth stage, and associated needs.

Moreover, contributors may have had different types of companies in mind when referencing specific headcounts.

For instance, Kunal appears to be referring to early-stage startups, where teams are smaller and tightly knit.

In contrast, Robert and others seem to be describing companies further along in their growth trajectory. 

Mark Siciliano, former VP of Enablement at a leading unified customer experience platform and current Strategic GTM Advisor at a revenue consultancy company, explicitly addresses this distinction, offering tailored advice for companies at different stages:

• Startups: “If you’re starting to hire sales reps and can’t personally onboard and train every new person, it’s a great time to put basic enablement in place. Start small – think playbooks, clear messaging, and light coaching.” Importantly, he notes this doesn’t necessarily mean building a full-fledged enablement function, which we’ll explore in more detail later.

• Scale-ups: “When your team hits around 10-15 sellers, you’ll need to build repeatable processes for training, onboarding, and metrics tracking. Focus on aligning sales, marketing, and product teams to ensure your messaging is consistent and your team is armed with what they need.”

• Enterprises: “In larger companies, enablement should be about optimizing what’s already working, building cross-functional alignment, and helping your team make sense of the data overload.”

He humorously sums it up: “

When hitting revenue goals feels like juggling flaming swords – blindfolded – while on a conference call, it’s time to build sales enablement.”

All of this raises an important question: if it’s not just about the number of reps, what are the true triggers for building a sales enablement function?

Scaling up and rapid growth

For most contributors, the triggers have to do with the company experiencing noticeable growth, which often coincides with heavy investments in the sales organisation.

This rapid scaling both in terms of the overall company and more specifically the revenue organisation brings with it new challenges that are best met with an enablement function.

The mere fact that the sales organisation is rapidly increasing in size soon becomes a trigger for building a sales enablement function as someone needs to ensure an efficient, repeatable process for hiring, onboarding, and continuously developing new sales reps. 

But once again, it is more than just adding more people.

Added responsibilities to existing personnel

The perfect example of what can happen when the sales organisation starts to grow noticeably is that some people may find themselves overwhelmed by the additions to their responsibilities:

• The best salesperson who used to enable and train the rest of the team is no longer able to do it due to more and more sales reps being hired. 

• Managers are spending much more than a couple of hours a week training reps. 

• Others within the organisation find themselves filling the gap of enablement in addition to doing their roles (e.g., product marketing or sales managers trying to build onboarding or other key enablement programmes).

At a certain point, it becomes too much and something has to give – most often, the people who have been jumping in to help become stretched too thin to do everything properly, and the sales organisation starts adopting ad-hoc solutions that develop into standard practices that can be very harmful later down the line.

Standardisation of processes

As opposed to ad-hoc solutions and practices, building an enablement function (even a one-person one at the early stages) can help standardise processes and practices that have been shown to work and which have to be scalable as the organisation grows. 

A few areas where standardisation is the key to success and that have been identified as triggers for building the function by our contributors include:

• Wide variability in sales performance across teams or individuals, which may indicate that there is a lack of repeatable sales processes and a path to closing and renewing or scalable sales motions and systems. 

• The ARR, TAM, and ICP have been identified, which makes it even more important to establish repeatable processes.

• There is bootstrapped training, content, processes, and so forth, and someone needs to start to own these items, professionalising them and moving them into circulation. 

• The reps on different teams are getting trained inconsistently because each manager is training them differently, which means that the training and development need to be standardised. 

• There is a need to rapidly accelerate the revenue growth to hit key milestones (e.g., funding rounds, board target requests), and the company is continuing to invest in sales hires. 

By acting as soon as these triggers are observed, the sales enablement function will be built just in time to establish a stable foundation for further growth.

Change management

A number of our contributors also mentioned various strategic changes to the sales organisation’s way of selling, the target market, the product, or the organisation as a whole as the signals to start building a sales enablement function, which will help with change management.

For instance, getting into new markets can be too much for the existing sales organisation to handle. This can include new geographies, new market segments (from SMBs to Enterprise), or new industries.

This expansion of the target market usually calls for new hires, new skillsets, new knowledge, new content, and even new sales processes to be executed effectively – all of which can be successfully addressed by introducing a sales enablement function.

Another trigger mentioned by our contributors are big product changes, such as introducing a major new product or making the existing product offering more complex, either due to adding new products or evolving existing ones (e.g., moving from selling products to offering solutions or services).

In situations where the product changes rapidly and more chaotically, a company might even consider adding a product enablement function.

Yet another change that our contributors mentioned was a strategic shift in sales approach, for example, moving from transactional selling to consultative or solution-based selling, or becoming more buyer-centric and focusing on buyer experience throughout the sales process.

Sheevaun Thatcher, former VP of Enablement at the global leader in customer relationship management (CRM) software and current Strategic GTM Advisor, was very specific and mentioned the situation when the product marketing team is pushing full product vs. customer-centric sales approaches as a strong signal to build the sales enablement function.

Sheevaun also pointed out that the company needs to have certain roles in place, such as CRO/SVP Sales and CMO/SVP Marketing.

Jill Guardia, the Senior VP of Revenue Enablement & Operations at a leading enterprise learning platform, mentioned something similar as one of the factors she takes into account:

“You’ve invested in a senior sales leader (e.g., VP Sales, CSO, CRO) and they are in growth mode and have a vision for how to work hand in hand with an enablement business partner.”

Alternative perspectives – starting early 

While many contributors identified specific triggers or milestones for building a sales enablement function, some advocate for integrating enablement practices from the very beginning, regardless of organisational size or the number of sales reps.

This foundational approach emphasises that the essence of enablement is not tied solely to headcount or growth stage but to the value it brings in aligning commercial efforts and establishing effective practices from the outset.

Embedding enablement from day one

Tom Greenwood, a Senior Sales Enablement Manager at a company behind a suite of multi-cloud infrastructure automation products, succinctly states that enablement should be considered “…anytime a sales team is hired.”

Timea Bara, the VP of GTM Enablement at a leading legal ediscovery software company, reinforces the idea that it’s never too early to start an enablement function.

She notes that while the role of enablement may evolve with the team’s maturity, early investment allows for the development of scalable and repeatable models. 

By establishing foundational practices, organisations can build upon them as they grow, ensuring consistency and efficiency in sales processes. 

Timea also emphasises the importance of considering full revenue or go-to-market (GTM) enablement rather than focusing solely on sales, ensuring that functions like customer success are not overlooked.

Enablement as a maturity spectrum

Jocelle Sarenpa, a Sales Leader & GTM Strategist at a tax compliance automation software company, offers a nuanced view, suggesting that enablement maturity is a spectrum and organisations will find themselves at different points along this journey over time.

Jocelle recommends using enablement maturity models to assess the current state and set intentions for desired outcomes. 

I propose my own sales enablement maturity model in this guide.

This approach allows companies to tailor their enablement efforts to their specific needs, potentially engaging consultants or fractional enablement leads to address urgent gaps without the immediate need for a full-scale function.

Enablement as a discipline

Dick Dunkel, the VP of Field Enablement at a company behind the leading enterprise data cloud solution, presents a similar perspective by viewing sales enablement as a discipline rather than strictly a function.

He suggests that building a sales enablement function doesn’t necessarily mean hiring dedicated resources immediately. 

Instead, foundational elements can be established early on by leveraging sales leaders or external expertise.

Dick emphasises the importance of creating a common language for qualifying, advancing, and measuring sales execution, even when the founder or CEO is still actively involved in sales calls.

By focusing on these fundamental principles, companies can ensure that core enablement practices are in place, setting the groundwork for future expansion of the function.

Organisational requirements for a thriving enablement function

Having explored when to build a sales enablement function, it’s equally important to understand the organisational conditions that allow the function to truly thrive. 

The reason I posed this specific question to the leaders involved in this piece is that, while we as enablement professionals bear a responsibility to strongly contribute to performance uplift, it’s equally crucial for organisations and their leaders to ensure the right conditions are in place.

Without this foundation, even the best enablement execution risks falling flat due to inadequate organisational support.

Several of the contributors referred back to their previous answers, highlighting the interconnectedness of timing and organisational readiness.

Based on the collective insights gathered, I’ve identified key conditions that foster a thriving sales enablement function. 

Leadership support and strategic alignment

At the heart of a successful enablement function is unwavering support from leadership, coupled with a strategic alignment to the organisation’s objectives. Nearly all of the contributors at least mentioned these as major factors.

Unwavering leadership commitment

The choice of the word commitment in the subheading above is deliberate.

I didn’t use terms like support or buy-in.

Commitment signifies that building a sales enablement function must be regarded as a strategic investment by the highest levels in the company to drive real impact. 

It is, as Mark Siciliano puts it:

“If your execs view it as a ‘nice-to-have’ instead of a strategic priority, you’ll be fighting an uphill battle.”

Many contributors also highlighted the distinction between merely ceremonial support and having “…complete understanding from C-Level of the benefits and value [of enablement],” as Kunal Pandya presents it. 

Lisa Duncan, the Senior Director of Revenue Enablement at a leading data intelligence company, did a great job of explaining how this commitment should come from the entire revenue vertical but also from other departments:

“Expectations set from the top that reps are expected to invest time in enablement programs; managers are bought in and committed to engaging with the programs and coaching their reps; people outside of enablement are willing to be subject matter experts (e.g., Product Marketing, Sales Engineering, Sales reps & leaders, Rev Ops).”

Robert Read also stressed that leadership commitment should extend to managers as well, saying it’s “incumbent on middle management to drive and support initiatives.” 

In addition to the quotes above, virtually all of the contributors mentioned sales or GTM leadership commitment as being an absolute prerequisite for sales enablement to thrive. 

It is equally important to point out, however, that they don’t see it as a one-way street.

In fact, a number of our contributors said how important it is for the enablement function to be formally held accountable by leadership.

Dick Dunkel for instance, advocates for the inclusion of a “…sales enablement steering’ function that sets priorities and is sponsored by the CRO”, as well as “a cadence of accountability with the CRO”.

However, as we all know, there can be no accountability without clear expectations and goals, which were also mentioned prominently by our contributors.

Clear expectations and measurable business goals

D’Andre Crump, the VP of Revenue Enablement at a market’s leading revenue-enablement-as-a-service consulting organisation, advocates for “clearly defined and measurable goals, initiatives, and outcomes” aligned with business objectives.

This clarity enables enablement to focus on initiatives that drive tangible results and demonstrate value.

Nate Vogel, the VP of Global Sales & Partner Enablement at a leading data and AI company, points out that thriving requires “…alignment with the leaders you serve and key definitions and data of the problems you are trying to solve.” 

By understanding the specific challenges and goals of the organisation, enablement can tailor its strategies effectively to address real needs.

While identifying gaps is a key responsibility of enablement leaders, clear direction from the top remains essential. 

Understanding of enablement’s role and trust in the process

One aspect of leadership support that is often overlooked by both the leadership group and the people who take on the responsibility of building out the function is the full understanding and agreement of what enablement is and isn’t. 

Without this, we can’t talk about the organisational trust in the process, which is essential for a function whose major results can only be observed after a certain period of time. 

Trafford Judd, the Senior Director of Revenue Enablement & Operations at a company behind leading AI software for workplace safety, mentions the common misconception that enablement is nothing more than training.

He points out that while training is a component, enablement encompasses a broader strategic role in enhancing sales effectiveness, reminding us that enablement is “not a quick fix but a pillar of a high-performing GTM team.

George Campbell, former VP of Enablement and current Enablement Strategist, emphasises that key stakeholders must “truly understand what enablement is, who owns what, and what an enablement leader or function is responsible for.”

This understanding facilitates better collaboration and support, ensuring that expectations are aligned.

George also advises leaders to “trust the ROI before the proof materialises,” acknowledging that while leading indicators may appear early, consistent business impact takes time to develop. Patience allows enablement strategies and associated execution to mature and demonstrate their full value.

Adequate funding and resources

I had to think long and hard about whether to include funding and resources under the previous section since they denote a certain strategic belief in the function and the fact that the leadership is providing full support to it. 

In the end, I decided to make it a separate section to reinforce the importance of the enablement function getting the appropriate funding to properly do its job. 

Lisa Duncan asserts that successful enablement functions “have the budget to invest in tools (LMS, CMS, conversation intelligence, etc.) and outside trainers as needed.”

Access to these resources enables the enablement team to create high-quality content, facilitate training sessions, and track progress effectively. Without the proper tools, the team’s ability to execute programmes and measure their impact can be significantly hindered.

George Campbell cautions against expecting “one person to be the silver bullet,” emphasising the need for a “suitable headcount and budget” to address the scope of enablement effectively. Overloading a small team or individual can lead to burnout and reduced effectiveness.

By providing adequate staffing, the organisation ensures that each area where enablement interventions could significantly uplift performance receives the attention it requires.

Investment in people is just as important as investment in technology.

D’Andre Crump stresses the necessity of “investment in the people/resources necessary to be successful.” This includes hiring skilled professionals who bring specific, context-relevant experience and expertise to the team.

A well-resourced team is better equipped to design comprehensive programmes, engage with the sales team, and drive meaningful results.

Tom Greenwood succinctly states that the organisation must properly fund the enablement function, reinforcing its strategic importance. Adequate funding signals to the entire organisation that enablement is a priority and that leadership is committed to its success.

This financial commitment also boosts the credibility and authority of the enablement team within the organisation.

Alignment and collaboration across departments

As I’ve pointed out myself on innumerable occasions, effective enablement hinges on the ability of teams like sales, marketing, product, customer success, and human resources to work cohesively.

Mark Siciliano puts it more descriptively – if these departments “don’t play well together, your enablement efforts will crash and burn.”

The essence of this collaboration lies in open communication and shared objectives, fostering an environment where each team understands and supports the others’ roles and contributions.

By building these strategic alliances, the enablement function can leverage expertise from each area, ensuring that enablement interventions are well-rounded and address the nuanced needs of the organisation.

Access to the sales team is particularly crucial.

Jocelle Sarenpa emphasises that enablement professionals need “access to the sales teams” and must not operate in a silo. Engaging directly with sales personnel allows enablement to tailor programmes that address real-world challenges, gather immediate feedback, and adjust approaches accordingly.

Moreover, the collaboration extends beyond just communication – it involves aligning goals, sharing resources, and coordinating efforts to avoid duplication and guarantee consistency. 

Culture and mindset

Among the many factors, it’s also important to understand the impact of the organisational culture on the success of the enablement function.

A culture that embraces learning, growth, and adaptability sets the stage for enablement to flourish and for the organisation to stay competitive in a rapidly changing market.

Lisa Duncan highlights the importance of cultivating a culture characterised by “curiosity, a growth mindset, [and] a culture of learning.”

In such an environment, employees feel free to seek continuous improvement, remain open to new ideas, and embrace the changes that enablement initiatives often bring.

When team members are eager to learn and grow, they are more likely to engage with enablement programmes and apply new skills and knowledge in their roles.

Embracing adaptability is also paramount.

Mark Siciliano notes that “sales enablement is a living, breathing function” that requires an organisational willingness to adapt. Resistance to change can hinder enablement efforts and impede progress.

If a mindset that views change as an opportunity rather than a threat is cultivated, organisations can more effectively implement new strategies and, on the other side of the spectrum, feel comfortable cutting initiatives that simply don’t pan out.

Learning from mistakes is another key aspect of a supportive culture.

Trafford Judd mentions the need for a culture that “fosters learning from mistakes and iterating.”

When enablement teams fear that every little mistake might spell doom for their budget or even existence, they are highly unlikely to show ambition or try out new things.

In short, a culture that values learning (which more often than not has to come from failure) and adaptability enhances the effectiveness of the enablement function and, perhaps even more importantly, contributes to the overall resilience and agility of the GTM organisation as a whole.

Team inception: Who should be the first enablement hire?

Now that we’ve explored when the right time to build the sales enablement function is and what makes for fertile ground for the function to thrive, it is time to start hiring. 

To start off, I presented our contributors with two similar but distinct thought experiments. 

The first one revolves around what kind of person would make for the ideal first enablement hire by the organisation.

The second one imagines a scenario where they themselves have already assumed this function-founding role and they are hiring their first additional team member.

The inaugural enablement hire – what to look for

When establishing the sales enablement function, the overall consensus describes someone who embodies a blend of strategic vision, practical execution skills, and cross-functional expertise. 

In my opinion, Lisa Duncan provided the most complete, clearly structured and yet succinctly expressed vision of the first enablement hire:

“The first hire should come in with a vision for what a world-class enablement organization could look like at this company, the ability to scale down that vision to the essentials based on available resources (and understand the tradeoffs in doing so), and a framework for how to scale and build up eventually to that world class vision. 

They must be able to develop the enablement strategy (by looking at data, talking to sales leaders and stakeholders) as well as design and run enablement programs (and have presence/credibility with the field). 

They need to be excellent communicators at all levels of the organization and be able to collaborate with many departments.”

Lisa’s initial starting point of someone with a strategic vision was echoed by a number of our contributors, such as George Campbell, Timea Bara, Mark Siciliano.

Nate Vogel was more concrete, saying that the first enablement hire should be able to run one or two strategic initiatives per quarter.

Similarly to this, wealth and breadth of experience would play a defining role in making the person suitable for this first role. 

Kunal Pandya, for instance, emphasises the need for someone with solid experience in building an enablement function, capable of defining a focused, strategic approach that delivers ROI. He points out that such a person may warrant a hefty salary, but that it is a mandatory expense.

Trafford Judd is another advocate for experience, specifically in mature enablement functions.

D’Andre Crump calls for someone with extensive experience and expertise across a variety of GTM motions, technologies, and verticals.

He explains that only such a profile will be able to, “…design enablement programs that cater to different sales strategies, customer segments, and market conditions.”

Samantha Thomspon, the Head of Revenue Enablement at an infrastructure-as-code platform for developers and Enablement Consultant, describes this person as a strategic growth partner, a “senior expert that’s still willing to ‘get their hands dirty’ to build the function with the end goal of positively impacting revenue.”

Samantha even describes the consequences of failing to hire an experienced leader first:

“Many companies fall into the trap of hiring junior enablement professionals or transitioning a seller into an enablement role. This ultimately does a disservice to everyone involved because the company won’t get the results they need and the enablement professional won’t have enough work experience (enablement, project management, or otherwise) to understand how to best build a function.”

She points out that this person should have between 6-12 years of experience but emphasises (in all caps, no less) that they should still be “HUNGRY to do more, build more, and challenge themselves.”

Samantha acknowledges that this unique combination of experience and the drive to be hands-on can be unicorn-level rare, but this is also something that other contributors mention.

Gary Manalus, the VP of Revenue Enablement at a leading HR automation platform, paints a vivid picture, saying that the first hire should have the, “ability to roll up sleeves and co-create with business and revenue leadership while the “paint is still wet”.

George Campbell and Timea Bara also call for someone who is a person of action.

Mark Siciliano calls that a builder’s mentality:

“You need someone who can create systems from scratch and isn’t scared of a blank slate. Think of them as part architect, part firefighter–designing processes and putting out the inevitable fires as the function gets off the ground.”

Another point that popped up regularly – a background in sales or some other customer-facing role. 

Trafford Judd mentions customer-facing (not necessarily quota carrying) experience, Timea Bara mentions the need for a strong understanding of pre and post sales, and Tom Greenwood is very specific when suggesting to “…only hire sales enablement professionals who have a significant sales background and are professional sales trainers with certifications.”

While Robert Read also supports the view that this first hire should have sales experience, he recommends a generalist:

“Generalists understand the bigger picture and give organisations better reach in the initial stages… you need someone who can review process, create remedial training and content and deliver it. As well as manage high-level stakeholders.”

Ross McLean, the VP of Revenue Strategy & Enablement at one of the most popular open-source data platforms, agrees:

“I would argue that you would be better starting with someone who can build out the foundations for the function vs. a specialised hire.”

Another major factor for our contributors is the ability to manage stakeholders, play a conduit role within the go-to-market organisation, and facilitate communication between departments.

Mark Siciliano calls it having the cross-functional ninja skills:

“This person needs to be fluent in both sales and marketing, with a dash of product knowledge for good measure. If they can’t navigate between departments like a pro, enablement’s going to be stuck in neutral.

Your first enablement hire is essentially the translator between sales, marketing, and leadership. If they can’t turn a complex strategy into actionable steps—or worse, they use buzzwords like “synergize” unironically—keep looking.”

Jocelle Sarenpa also provides an elegant description of this aspect of the first enablement role within an organisation:

“…revenue enablement exists to bridge the gap between the initiatives of the executive team and the sales, CX, and partner teams in the field. The pioneering first enablement hire should be someone who can understand both sides of this gap and help be the conduit towards achieving the initiatives set forth by the executive team by enabling the customer-facing teams with the skills, knowledge, and understanding of their impact to achieve the initiatives in an efficient and effective way.”

Trafford Judd, George Campbell, and Timea Bara all reinforce this idea of someone who engages the stakeholders and facilitates communication across the organisation. 

The list of “requirements” for this role doesn’t end here.

Guided by their experiences and expertise, they suggest many more skills and traits that would make someone the right first enablement hire:

• Onboarding design skills

• Adaptability and agility

• Sales technology skills

• Data analytics skills to know how to collect and analyse metrics like program adoption, sales productivity, and revenue impact

• Understanding of human motivation and talent management

• Training and coaching expertise

• Culture-building abilities

• Ability to attract and hire the best enablement talent 

• Willingness to challenge and take risks

Mark Siciliano sums it up perfectly:

“Hire someone who’s part strategist, part therapist, and part drill sergeant. You need a person who can build the plane while it’s flying—because that’s exactly what they’ll be doing.”

Some of our contributors saw the first enablement hire as being (almost) exclusively determined by what the organisation needs at that moment. 

For example, Dick Dunkel provided a series of questions that have to be answered in order to identify what kind of a skillset this first hire should have:

“Do they need to build the foundation of sales process, qualification methodology, measurement plan, as the organization prepares to scale?   

Do they need to focus on leveling-up the in-field seller’s product knowledge? 

Do they need to focus on establishing internal alignments between sales leadership, product and product marketing?  

Do they need to focus on sales strategy and helping formulate and deliver sales plays to the field?”

As he puts it, “Getting the leaders aligned on these kinds of priorities will make all the difference in finding the right fit.”

A few of the contributors offer alternatives to going straight for a strictly enablement hire.

George Campbell, for example, suggests that sometimes the best approach is to hire a consultant to help establish core programmes, then to hire a full-time enablement employee(s) to sustain delivery and maintenance.

In Jill Guardia’s opinion, in the early stages, it is best to keep a strong B seller whole financially and give them a support role to help train and enable other sellers. She continues:

“As the team grows and you need more enablement support, I would look for someone who has program and project management experience and can spend time building relationships and interpreting business needs to drive thoughtful business outcomes.” 

Expanding the team: who would you hire first?

To dig even deeper, I asked our contributors to consider a scenario where they are already leading the enablement function and are now tasked with building a team. Specifically, I wanted to know what kind of profile they would hire first in this situation.

For many of our contributors, it would be a doer, someone who can own and manage programmes. 

Mark Siciliano emphasises the need for someone who, “…knows how to take a strategy and make it happen. They’re not afraid to roll up their sleeves and dive into the details, whether it’s building onboarding programs, running training sessions, or creating killer sales content. Forget fluff—this hire is all about getting things done.”

Mark calls this person the execution master.

Lisa Duncan would bring on someone strong in programme design and execution, training facilitation, project management, and communications – a real doer who can take ownership of key programmes and has experience working closely with sales teams. 

Robert Read, D’Andre Crump, Jill Guardia, Gary Manalus, and George Campbell would also go for someone who is comfortable with delivering specific programmes and “co-creating with business and revenue leadership while the “paint is still wet”, as Gary puts it.

Samantha Thompson provides a unique perspective on this matter since she is in the middle of this exact process:

“This is something I’m living now as Pulumi’s first enablement hire and hoping to hire for my first role in a few months. 

Now that I have core, foundational programs built and we’re beginning to scale the team it’s quickly becoming too much for one person to manage AND I’m still getting pulled into new strategic initiatives. 

For this first hire I’ll be looking for someone with 4+ years of enablement experience that’s a strong generalist that can take over a number of those foundational programs for the sales teams and continue to innovate and report on their effectiveness. 

This will allow me to continue to go and build out new lines of enablement for our technical teams (SE/CSA/Support/Pro Services) and then bring in more folks to support those once those next batch of programs are built. 

What’s most important is this person also has a passion for enablement, a bias for action, and is eager to own critical programs for our field teams.”

Many of the contributors also said they would bring on someone with extensive sales experience, both because they understand what their “audience” needs to excel from a practical perspective and because they can emphatise with the front-line sales personnel. 

Hiring individuals with complementary skills and diverse backgrounds is also a common theme.

Jocelle Sarenpa aims to build a well-rounded team by adding members who bring different skills and experiences to hers – teammates who understand instructional design and learner curriculum, complementing her own background in sales and facilitation. 

Dick Dunkel has the same approach:

“Given that I’m pretty good at content creation and strategic alignment, my first hire would be for reporting and analytics.”

Analytical thinkers are also highly valued for their ability to add depth and a kind of backing for the team’s strategic capabilities.

Kunal Pandya seeks an analytical enable to enhance the team’s ability to use data for decision-making and strategy development. 

D’Andre Crump would hire someone with a combination of analytical expertise and programme management who would lay the foundation for planning, measurement, and execution as the enablement function starts to achieve early-stage results.

Mark Siciliano also mentioned bringing on someone who would help set up the sales enablement process the right way:

“The first hire has to bring structure where there is none. This means someone who loves checklists, dashboards, and making things run smoothly. I need a process nerd, someone who will help turn chaos into order—and can spot inefficiencies from a mile away.”

Tailoring the hire to the organisational context

It’s important to note that the ideal profile for both making the initial hire and bringing on that extra enablement person should always be based on your company’s specific needs, maturity level, and strategic priorities. 

In short, understanding organisational priorities is a foundational element. 

Nate Vogel, Sheevaun Thatcher, and Timea Bara all recognise the importance of onboarding skills in early hires in the majority of companies building the function.

Strong project management skills are also valuable for coordinating complex enablement initiatives with a limited headcount. 

Flexibility based on maturity is also important.

Timea Bara mentions that the maturity of the company influences the type of hire needed.

Depending on where the organisation is, you might start with an onboarding enablement partner or focus on product, process, or systems enablement. 

Jill Guardia drives the point home in a few words –  there is no one-size-fits-all approach. It depends on the organisation’s current state and specific needs.

Assessing these factors will help determine the most impactful hire.

You can also consult these 67 sales enablement interview questions that will increase your chances of ma

Growing the team: adding two more members

As your sales enablement function begins to take shape with your initial hires, the next step is to strategically expand the team to address the evolving needs and expectations of your organisation.

Adding two more enablement professionals allows you to deepen your capabilities, support a broader range of initiatives, and drive greater impact.

Our contributors provided valuable insights into how they would approach this phase of growth, emphasising the importance of aligning enablement new hire choices with specific business priorities and strategic goals.

Before making additional hires, as already highlighted, it’s key to evaluate the current state of your sales organisation and identify the most pressing challenges and opportunities. 

Samantha Thompson points out that the decision “entirely depends on how successful the company is and how many folks enablement is supporting and the roles they’re in.” 

Sheevaun Thatcher shares similar advice:

“I would first inquire of sales leadership their priority hiring … segmented, geo, named account, upmarket, SMB, inside sales. If segmented, then I would look for people who have worked in those segments (small business, midmarket,enterprise).”

Dick Dunkel and Ross McLean did provide some suggestions, but both of them started off by saying that the next hires would be based on the strategic goals and priorities of the company.

Jocelle Sarenpa expands this by considering both short-term and long-term priorities of the enablement function and the organisation as a whole:

“It is equally important for to me to consider the short term priorities and struggles we need to overcome today, but also the future state of revenue and preparing the team to adapt to scale and lead initiatives that support the future state. 

This will define what is required of adding new members to the team, reflections like where are we today and how did we get here? Where do we want to go and what do we need to get there?”

Many contributors suggest bringing on specialists who can address specific needs within the sales enablement function. 

For instance, rapid growth often necessitates a robust onboarding programme to ensure new hires become productive quickly. Tom Greenwood and Gary Manalus both recommend hiring an onboarding specialist to focus on this critical area.

Developing high-quality training materials and resources is also an important component of effective enablement. 

George Campbell would hire a “training and enablement coordinator” to manage the Learning Management System (LMS), scheduling, tracking, and reporting, ensuring that enablement programmes run smoothly and efficiently. 

Nate Vogel highlights the need for someone who can “build instructionally designed courses (e.g., e-learnings, micro-learnings)”, enhancing the team’s ability to deliver impactful training content.

Mark Siciliano suggests adding a content and collateral guru who can transform complex product information into compelling messaging that sales reps can use in real conversations. Mark makes sure to emphasise that this is,

“…not just someone who knows how to slap together a deck, but someone who can turn complex product info into killer messaging that sales reps can actually use in real conversations.

This person is in charge of ensuring that every battle card, one-pager, and case study is on point, up to date, and easy to access (because let’s be real, if it’s buried in a folder somewhere, it’s dead to sales).”

Enhancing the skills of the sales team through focused training on sales methodologies is another area of focus.

Gary Manalus mentions hiring for “sales methodology and sales skill development” to elevate the team’s effectiveness.

Empowering sales leaders and enhancing their coaching capabilities can have a significant multiplier effect on sales performance.

Nate Vogel would bring on someone who can “drive enablement for leaders,” helping to scale the impact of enablement efforts through effective leadership development.

This focus on leadership enablement ensures that managers are equipped to coach and develop their teams, fostering a culture of continuous improvement and reinforcing what’s being thaught through enablement programmes. 

Jill Guardia considers investing in someone with “a true coaching background” to support leaders in becoming better coaches.

Similarly, D’Andre Crump would hire someone to “specifically work on upskilling first-line leaders.” As most leaders would agree, managers are the real multipliers and even the best enablement initiatives will fail without their coaching and support. 

As the enablement function grows, so does the need for operational support and data-driven decision-making.

Mark Siciliano recommends hiring a “metrics and operations wizard” who lives and breathes numbers.

He elaborates:

“This person will help me track what’s working and what’s not—because if we’re not measuring it, we’re guessing. They’ll make sure we’ve got the right data to prove the ROI of our enablement efforts and continuously optimize everything we’re doing. Think of them as the person who makes sure we’re not just running around being busy, but actually moving the needle.”

Timea Bara suggests adding an operations specialist who deals with sales tools and analysis, enhancing the efficiency and effectiveness of the enablement function.

By focusing on operational efficiency and analytics, it becomes easier to make informed decisions, allocate resources effectively, and demonstrate the value of enablement to stakeholders.

Tailoring enablement efforts to specific roles, market segments, or geographical regions can enhance relevance and impact.

Trafford Judd would hire specialists for roles such as Account Executives (AEs), Sales Development Representatives (SDRs), or Customer Success Managers (CSMs); or focus on segments like Enterprise, Mid-Market, or SMB, depending on the business model.

Kunal Pandya mentions the possibility of regional specialists, suggesting that as organisations expand geographically, regional enablement specialists become valuable.

In cases of significant product initiatives, Sheevaun Thatcher would consider hiring a “product enablement person” to liaise with Product Marketing and ensure sales teams are equipped to sell new offerings effectively.

Sales enablement dream team of six

In an ideal scenario, where resources are abundant and the sales enablement function is poised for significant impact, assembling a team of six or more members allows for specialised roles and a comprehensive approach to supporting the sales organisation. 

While such an investment is typically seen in larger companies, exploring this “dream team” concept provides valuable insights into how an enablement function can be structured for maximum effectiveness. 

As already touched upon in previous paragraphs, the recurring theme among the contributors is the importance of structuring the enablement team to align closely with the company’s strategic objectives, growth plans, and organisational structure.

The team should be designed to support the specific needs of the sales organisation, whether that’s by role, geography, product focus, or strategic initiatives.

For instance, Lisa Duncan suggests that for a global team, the structure might include programme managers dedicated to product training, different sales roles (such as Business Development Representatives, Account Executives, and Customer Success Managers), frontline manager enablement, and new hire onboarding. This approach ensures that each critical commercial area receives focused support.

Similarly, Mark Siciliano emphasises dividing the team based on roles that cover essential aspects of the enablement function. His proposed team includes a training and development lead, content and collateral manager, sales enablement software and technology specialist, metrics and operations analyst, regional enablement specialists, and a sales coaching expert.

This structure covers the spectrum from onboarding and training to content management, technology optimisation, data analysis, and coaching – essentially, some of the main pillars of sales enablement, as discussed in my sales enablement guide.

Specialisation allows team members to develop deep expertise in specific areas, enhancing the quality and effectiveness of enablement initiatives. Common specialised roles mentioned by the contributors include:

• Onboarding programme owner: Responsible for designing and managing the onboarding process to ensure new hires become productive quickly.

• Product training manager: Works closely with product marketing and solutions consultants to keep the sales team trained and updated on product developments.

• Sales methodology and skills development specialist: Focuses on enhancing sales techniques and methodologies across the team.

• Content and communications manager: Manages the creation and distribution of sales content, ensuring consistency and alignment with brand messaging.

• Tools and technology specialist: Optimises the sales enablement technology stack, provides training on tools, and ensures seamless integration and adoption.

• Metrics and operations analyst: Tracks performance metrics, analyses data to inform strategies, and demonstrates the ROI of enablement efforts.

• Regional or role-based enablement partners: Aligns with specific regions or sales roles to provide tailored support that considers local market nuances or role-specific challenges.

(Check out this article on sales enablement roles and responsibilities for more details.)

For organisations operating across multiple geographies, balancing global consistency with local relevance is an interesting and important undertaking.

Several contributors advocate for a structure that combines global programme managers with regional specialists.

Lisa Duncan proposes having global programme managers for key areas like product training and frontline manager enablement, complemented by programme managers aligned to each geographical region. These regional managers partner with local sales leaders to identify needs, develop strategies, and localise global sales enablement initiatives.

Similarly, Mark Siciliano includes regional enablement specialists in his team to address unique challenges in different markets. By ensuring that training, content, and strategies are adapted appropriately, this approach prevents a one-size-fits-all methodology and respects cultural and market differences.

Effective sales enablement teams function as hubs that connect various parts of the organisation.

Most leaders stress the importance of roles that facilitate communication and collaboration across departments and between leadership, management, and individual contributors.

For example, Jill Guardia includes roles focused on communications and events, incentives, and culture-building programmes. These roles help maintain alignment, promote a positive sales culture, and ensure that initiatives are effectively communicated and acted upon.

Developing the coaching capabilities of sales leaders and fostering leadership within the team amplifies the impact of enablement efforts. Roles dedicated to coaching and leadership enablement are considered valuable additions to a dream team. 

Nate Vogel suggests including someone who can “drive enablement for leaders,” enhancing the coaching skills of sales managers, and promoting effective team leadership. These positions represent the real performance multipliers because if they operate effectively, the rest of the sales teams below them will more likely do so, with higher levels of motivation and accountability. 

Some contributors, like Timea Bara, propose creating a Centre of Excellence within the enablement team. This sub-team focuses on areas such as product, systems, and tool enablement, as well as managing experience and excellence programmes like sales kick-offs, recognition events, and internal communications.

While the idea of a six-member enablement team is appealing, it’s important to consider the organisation’s size, resources, and growth stage. Samantha Thompson cautions against expanding the team unnecessarily, emphasising that “small but mighty enablement teams can move mountains.”

She advocates hiring the right people at the right seniority level, investing in the right sales enablement technology, and ensuring clear roles and responsibilities.

Jocelle Sarenpa would use this relatively large team to ensure that enablement is truly ingrained within the organisation, from the C-level to individual contributors:

“Understanding the pulse of the revenue teams, what is happening not just from a dashboard view, but from really being involved in what is working in the field and what is not to achieve the initiatives of the organization, while also being aligned to the strategic initiatives of the organization to be effective in orienting the revenue teams.“

She also mentions something that is often forgotten, and that is the fact that enablement is a field that tends not to get bogged down in prescribed, for-life roles:

“In any team model, we can’t lose sight of the evolution of enablement and the professionals within the function. 

As a character trait, enablers are adaptable and we love to learn! 

In your teams, offer opportunities to grow beyond the scope today through mentorship and networking, development opportunities like coursework or certifications to stay sharp for the revenue teams!”

Immediate priorities in terms of strategy and resources

Having explored the optimal team structures and roles for a thriving sales enablement function, it’s essential to consider the immediate priorities when building this function from the ground up.

By being thorough and setting everything up properly at the very beginning, a newly established enablement function will set itself both for short-term and long-term success.

Conversely, bad decisions made in the first days can easily have a compounding effect, turning the enablement department into a cost centre that has no to little impact on the sales success. 

Our contributors shared valuable insights on what should be the focal points in terms of strategy and resources during this critical initial phase.

Mark Siciliano was kind enough to provide something of a roadmap on how to approach this.

Since it is arguably the most complete of the contributions on this issue, we will take his step-by-step process and reinforce his insights with additional ones from other contributors. 

Mark proposes first getting the lie of the land (Assessment Phase). 

To quote him:

“Before doing anything, you’ve got to understand the current state of sales. If your reps are closing deals based on gut feelings and improvisation, you’re in the Wild West, and enablement needs to bring some order.”

He also proposes a way to do this – by conducting a needs assessment:

“Look at sales performance, tools in place, current training gaps, and how well aligned sales is with marketing and product. Get leadership’s input too—so you’re not building in a vacuum.”

Lisa Duncan advises doing a listening tour with reps and managers to uncover other needs they have, while Sheevaun Thatcher describes it somewhat differently:

“Deep analysis of what is working and what is not working, determining what is fixable, creatable, or dismissable.”

Tom Greenwood advises “understanding the sales process/stages within the CRM system”, which will subsequently guide the building of sales enablement initiatives.

Jocelle Sarenpa went into more detail about how to figure out where the GTM organisation stands. She suggests “establishing a baseline of where the sellers are today; a holistic view of the health and performance of the revenue team.”

Jocelle then goes on to identify the metrics that can help with this:

• e-NPS (employee net promoter score)

• overall tenure time

• sales performance data like sales velocity at an organization level, sales team level, and individual level. 

She also advocates performing competency mapping, a process which defines the skills, knowledge, characteristics, and behaviors that employees need to perform their jobs effectively. Defining competency should be outlined by role, and each individual can be measured.

Finally, she suggests painting up with business partners in HR, L&D, and Sales Leadership to help contribute to competency mapping. 

The importance of the competency framework is mentioned as one of the key priorities (or steps) by George Campbell and Robert Read as well.

The next priority should be alignment with leadership which goes beyond CRO putting down an endless and unrealistic list of goals that enablement has to achieve.

As Mark Siciliano describes it: 

“If leadership doesn’t know what they want from sales enablement, you’ll be playing the role of a firefighter with no water hose. Get clarity on the specific outcomes they expect. Is it ramping up new hires faster? Closing bigger deals? Scaling into new markets? Make sure you’re aligned with what actually matters to the C-suite, or you’ll end up building stuff no one cares about.”

For Mark, the immediate priority is to align enablement’s strategy with business goals – whether that’s hitting certain revenue targets, improving win rates, or shortening sales cycles.

Jill Guardia advises something very similar:

“Firstly, spend time with your leadership and executive team building the business case for the investment. Build a FY plan that includes assessing, training, communications and other lifecycle considerations and ensure that you include input from many in the organization.”

In one way or another, almost all of the contributors mention this alignment as one of the key early priorities

Creating an enablement charter can be a great tool to help you formalise this alignment.

Both Sheevaun Thatcher, George Campbell and Gary Manalus advocate for publishing and vocalising a charter that defines accountability and outlines the mission, vision, scope, goals, and measures of success for the enablement function.

This charter serves as a foundational document that sets clear expectations and prevents the team from becoming a catch-all for non-strategic tasks.

Gary warns that in newer organisations, this may involve additional work,

“… enablement leaders need to teach and coordinate with the rest of the business how to best activate the sales teams. Sales Managers and Directors need to buy-in early on their role in coaching and training their teams so this does not fall all on enablement, and that ongoing adoption is achieved.”

Once everyone agrees on what enablement is doing (and what it isn’t) and all of the stakeholders are on board, it is time to start working on highest priority initiatives, getting those quick wins that will establish the function as a true contributor.

Once again, we go to Mark Siciliano:

“Focus on one “quick win” that gives the sales team value—like revamping onboarding or creating a simple, clear messaging playbook. Small victories build momentum.”

Other contributors also advocated for laser-sharp focus in the early days, suggesting areas where enablement should go all-out initially.

As Timea Bara puts it:

“The most important is to have FOCUS and not try to do too much.”

For Sheevaun Thatcher, it starts with sales and marketing alignment:

“Work with Marketing to ensure that their relationship with Sales provides a win-win for both. Marketing gets adoption of content, Sales gets content they can use. Then ensure that there is a one-stop-shop for all assets, that those assets are aligned with GTM and there is ONE VERSION of them.”

For George Campbell, it’s two main early areas of focus:

• Training and enabling managers “…to become day-by-day enablers/coaches, as this ensures long-term reinforcement & consistency of key learning” 

• Creating a central hub of core resources – “This could be within the LMS or simply a share point so that all end users know where to find critical info.”

Robert Read has a clearly prioritised list of actions:

“First ensure that the business has understood the ICP, second link that to marketing and content. Now you can look at skill-gapping the GTM team using competency work. From there choose an appropriate methodology to pin against the competencies and ICP. Create onboarding based on the needs of the roles taking the above into account.”

Onboarding came up relatively frequently in our contributors’ answers, probably due to the fact that the enablement function is usually first built-out in order to help with a sudden increase in sales hiring.

Lisa Duncan also has a list of “table stakes” as she calls them, the foundational basics that are in most cases what has to be done first:

• New hire onboarding programmes

• A well organized CMS

• Product training

• Basic sales process

• Tech stack training

Trafford Judd sees sales enablement assets as the key area in the early days of the function,

“…making sure the right sales enablement content is available at the right time, in the flow of work. By content, I mean customer-facing as well as documentation, sales plays, battlecards, process, and job aids.”

Mark Siciliano also stressed the importance of sales enablement content:

“…start with the basics: playbooks, training materials, and the tools sales need to do their job”, while warning about overdoing it, “But don’t over-engineer it. You don’t need a 50-page document no one will read. Prioritize things that will actually get used.”

The final piece of the puzzle in the earliest days of the function, at least for our contributors, is deciding on the metrics that will be tracked as part of a data-driven enablement measurement framework.

This is key to understanding how impactful the early efforts are, is everything progressing according to the charter and the roadmap, and whether there is need to adjust what the team is doing.

Finally, a number of the contributors mentioned sales enablement tools such as content management systems, e-learning solutions, and conversational intelligence software.

Samantha Thompson shared her initial priorities in the form of a 90-day plan:

“1st week: 

• Decide on your project management tool, templates, and enablement calendar ASAP.

1st month: 

• 1. Craft your enablement charter and share on an all-hands to set expectations and build excitement. 

• 2. Deliver your first training session with the team to build credibility.

90 days: 

• 1. Build role-specific onboarding programs by 90 days. 

• 2. Audit all existing sales collateral and create a central repository. 

• 3. Work with your cross-functional teams to craft unified GTM messaging / pitches to certify the team on”.

For reference, if you wish to read about how I personally approach the early days of the enablement function (as well as the long-term focus), check out my article on building a winning sales enablement strategy.

Key metrics to focus on in the first 12-to-18 months

As you establish and develop your sales enablement function, selecting the right metrics to track is a necessary foundational steps for demonstrating value and guiding strategic decisions. 

In the early stages, focusing on metrics that align closely with business goals and directly impact revenue will help build credibility and support within the organisation. 

Our contributors highlighted several key metrics that are essential to monitor during the first 12 to 18 months: 

• Ramp time for new hires: Reducing the time it takes for new sales reps to become fully productive is a common priority. Several contributors, including Mark Siciliano and George Campbell, highlight ramp time as a critical metric. Tracking how quickly new hires reach full quota attainment or close their first deals provides insight into the effectiveness of your onboarding programmes. Improving ramp time not only accelerates revenue generation but also boosts team morale and retention.

• Quota attainment: Monitoring quota attainment is essential to assess whether enablement efforts are helping sales reps meet or exceed their targets. As Lisa Duncan notes, standard lagging indicators like quota attainment and sales productivity per representative offer a clear picture of performance improvements. 

• Win rates and conversion metrics: Improving win rates – the ratio of deals won versus the total amount of deals pursued – is a strong indicator of the effectiveness of your enablement initiatives. Contributors like Robert Read and Sheevaun Thatcher suggest focusing on metrics such as qualification rates, stage advancement rates, and conversion rates between sales stages. These metrics help you understand how well the sales team is moving opportunities through the pipeline and where they may be encountering obstacles.

• Sales cycle length and deal velocity: Shortening the sales cycle length is another important metric. A reduced sales cycle means that deals are closing faster, leading to quicker revenue recognition. Mark Siciliano points out that enabling reps to move deals through the pipeline more efficiently is a sign of impactful training and processes. Monitoring deal velocity also allows you to assess the efficiency of the sales process and make necessary adjustments.

• Pipeline generation and health: Evaluating pipeline generation and overall pipeline health provides insight into the future revenue potential and the effectiveness of prospecting efforts. Lisa Duncan recommends looking at metrics like pipeline coverage, the time deals spend in each stage, and whether the next steps are in place. Samantha Thompson tracks pipeline creation at 30, 60, and 90-day intervals to measure the ongoing impact of enablement programmes on pipeline development.

• Content usage and effectiveness: Ensuring that the sales team utilises the resources provided is essential (as long as such resources are timely and relevant). Tracking content usage helps determine whether materials like playbooks, battlecards, and case studies are being adopted. Mark Siciliano advises monitoring content adoption rates and linking them to win rates and deal velocity to assess their effectiveness. If content is not being used, it may indicate a need for better alignment or more relevant materials.

• Training completion and application: Measuring training completion rates and the application of learned skills provides insight into the effectiveness of your training programmes. Assessments, certifications, and conversational intelligence tools can help evaluate how well reps are retaining and applying knowledge. 

• Behaviour change indicators: Focusing on leading indicators of behaviour change allows you to assess the impact of enablement initiatives on day-to-day activities. Ross McLean emphasises the importance of observing evidence of behaviour change and creating cohort analyses that link these changes to outcomes. 

• Sales productivity metrics: Analysing how sales representatives allocate their time can reveal opportunities for increased efficiency. Mark Siciliano suggests measuring the proportion of time spent on selling versus non-selling activities. 

• Employee engagement and confidence: While more qualitative, tracking seller confidence and engagement can provide valuable insights. Confident, motivated sales reps are more likely to perform well. Surveys or interviews can help assess changes in confidence levels following training or new initiatives. 

• Customer success and retention metrics: If your enablement function also supports customer success teams, metrics like churn rate and customer engagement metrics become important. 

Additional advice from our contributors

I’ve made it a tradition to ask our contributors to share additional insights, advice, or even cautionary tales that didn’t surface while answering our questions.

Personally, I love this section because you never know what unexpected wisdom you might discover.

Let’s find out together!

Kunal Pandya:

“An enablement function must be built from the start with strategic vision along with a broad remit.  A tactical function focused on a narrow remit of onboarding, training and content management will only be seen as a cost center.”

Lisa Duncan:

“Focus is key. There is so much an enablement function could potentially do for a sales org, but it’s important to be able to prioritize and stay focused on a few key initiatives that will really move the needle rather than spreading resources thinly across many topics and programs without having a measurable impact.”

Robert Read:

“Be flexible. And do not focus on ‘one and done’ enablement. Enablement is a continuum and requires management support and technology investment to see real advancement.

Also, businesses need to realise enablement is not a quick fix.  It takes time.  Research shows that it takes 30 role plays to see real improvement in behaviour and skills so be patient and understand the enablement program of today will only show real delivery in 6 to 12 to 18 months.  

No program should be run without proper success criteria and reporting against bottom line metrics.”

Sheevaun Thatcher:

“The success of the function is directly related to the relationship between enablement leaders and sales leaders. They must be partners in order for programs to be successful.”

Tom Greenwood:

“AI has to be a consideration.”

Nate Vogel:

“One of my biggest mistakes made (lessons learned) was not to train and enable front-line managers first on any major enablement initiative so they can help reinforce the training but also model the right behavior. I have found when you do this first, your success of launching that enablement will have a much higher chance of success when your leaders being the change agents.”

Dick Dunkel:

“When building a sales enablement function, it’s critical to build a team culture and that team culture needs to be complementary to the sales culture.  If they are quarterly driven, then you are quarterly driven.  If sales leaders are driving a culture of sales excellence, then sales enablement must have the same kind of commitment.  Sales and sales enablement can be each other’s accountability partner in their shared commitment to sales excellence.”

Jocelle Sarenpa:

“I had an interview a few years ago where the hiring manager told me, ‘I think we are hiring for enablement WAY too late’. 

That should have made me run for the hills! Instead, I put my sales hat on and I got curious.

 Why was it too late? What has happened in the time of establishment until today? What bottlenecks has this caused? What other departments were impacted? What were the downstream effects? What was the cost of having no enablement function? What do you believe would be the state of revenue if you had an enablement function? What problems would disappear? 

The responses were eye-opening, for both parties! And the hiring process seemed far more urgent after this discussion. 

The truth is, if your company is still in good health, it is not too late to start an enablement function. Recognizing what the need will be before you actually need it, and having the ability to take action is not a luxury many companies have. 

If you are thinking about starting an enablement function at your organization, it is not too late! 

‘The future depends on what you do today’ – Mahatma Ghandi”

Samantha Thompson:

“Staying agile, constantly checking in with your stakeholders, and being open to taking on items outside of enablement’s traditional scope are essential to proving your worth and ultimately growing your impact and function. 

However, for any project you’re asked to contribute, be sure to ask “why?” Said more explicitly…Make sure you understand the business challenge you’re being asked to address, the intended impact or change in behavior, and how enablement specifically will help address that business challenge and performance improvement.

When done right and embraced for the beautiful mess it is, you’ll be hard-pressed to find a more engaging and rewarding role in enablement! It’s why I’ve sought it out 4 times over.”

George Campbell:

“Ensure that the target audience is ‘match-fit’. There are lots of enablement solutions & methods, and there is an obvious attraction to bite-sized learning… however, if organizations truly want a high-performing culture, then getting back to basics is critical, and employees need to be “training” regularly.

This does not mean traditional classroom sessions (it can), but more so that a growth mindset should be embedded with all employees, so that there is as much habitual routine on exploring improved ways of doing things, as with other disciplines.”

Conclusion

Like most things related to sales enablement, there is no one-size-fits-all approach to building the function that guarantees success.

It is far better to invest time in understanding why you need the function, what you aim to achieve, and seeking advice from experts who have successfully navigated this journey.

This ensures you can create an environment where the enablement function can thrive – allowing your sales organisation to flourish as a result – rather than rushing into setting up a passive, tactical firefighting unit with poor practices.

While course corrections are always possible, starting off in the wrong direction can hinder your sales enablement team’s ability to significantly impact your organisation’s sales performance.

Our contributors have made it clear that every decision you make – starting with the initial one to build the function – depends on context, the current state of your sales organisation, your goals, budget, and more.

I hope the insights in this article guide you towards asking the right questions and making the best decisions.

A huge thanks to D’Andre, Dick, Gary, George, Jill, Jocelle, Kunal, Lisa, Mark, Nate, Robert, Ross, Samantha, Sheevaun, Timea, Tom, and Trafford!

I am confident that your incredible contributions will guide sales leaders, founders, CEOs, and other enablement professionals in making those right decisions and taking effective action, ultimately advancing the enablement profession.

In case you are looking for a more practical advice, I’ve also written another article on setting up the right sales enablement team structure.