Jennifer Dougherty
Table of Contents

Jennifer Dougherty is the Head of Enablement - Americas at Airwallex. She has over a decade of experience in Sales, ranging from training to operations and enablement. Airwallex works to provide the global financial infrastructure and applications to empower businesses to operate anywhere, anytime.

In this interview, Jennifer delves into why and how change management needs to be at the center of enablement. She also discusses how enablers need to understand revenue impact in-depth before rolling out multiple enablement initiatives and the importance of fostering partnerships within the organization and working together towards success. 

(This conversation has been edited for length and clarity.)

Enablement and the economy

I have worked in organizations at both ends of the spectrum, where the CRO believes in the power of revenue enablement and organizations where the investment in enablement could be more substantial. This has made me keenly aware of the difference robust enablement programs can bring. 

The current macro-economy has caused several issues in sales. Many people are struggling to hit their numbers. Not just organization-wide but individually, numerous sales professionals who have always found success are struggling. 

As we are witnessing, this leads to workforce reduction and enablement getting hit. However, I also see a lot of positive signs. For example, Gartner has come out with a recent study stating that enablement in these difficult selling moments will be more critical than ever and that successful organizations will invest more heavily in enablement.

Metrics of enablement

Enablement needs to discuss the metrics and the goals they can align with their stakeholders to elevate their role. Elevating the role and goals of enablement starts with addressing specific issues throughout the sales cycle. For instance, if you're having problems converting at the start of your sales cycle, creating certification programs that address a specific issue or topic will be incredibly helpful. 

It's essential to know and understand what the baseline is and what the metrics are before the program kicks off. Subsequently, over the next six months, as an enabler, you need to ensure you are reporting back improvements on those metrics. 

If you improve a metric anywhere in the sales cycle, that improvement will have upstream and downstream effects.

Further, having a macro view of the entire cycle is essential. For instance, you're working on elevating your discovery for higher conversion to your third sales cycle, which is typically evaluating or ‘solution-ing.’ Simultaneously, you're focusing on the next sales stage to ensure that the power of what you created early on in your sales cycle continues. It's never just a single sales skill you're thinking about, even if you are rolling out a certification program on discovery. It's all about thinking of how you continue that string throughout the sales cycle.

Typically, enablers are always looking at ramp time for new employees, although companies are not hiring at that rate anymore, making it just table stakes at this point. Some metrics don’t just signify conversion early on in the sales cycle but also demonstrate revenue impact. When you roll out these programs, the revenue impact is often unclear. So, when defining your baseline, enablement needs to look at the average deal size and win rates. 

Suppose you have a 2 or 3-percent increase in your win rate; you're simultaneously focussing on reaching your average deal size. The revenue impact can be significant.

It's never just a single thing. The importance of partnerships within the organization and celebrating as a team cannot be exaggerated. For instance, if enablement is rolling out a certification program, you need content and assets that go with that. Product marketing also gets to shine when we roll out these programs. Enablement needs to remember they're a part of a puzzle to define the essential metrics.

Developing partnerships paves the road to success. 

Enablement must ensure the sales operations managers know what you are coaching and training toward. They can piggyback off that, and as they're doing deal inspections with their teams or working on forecasting, they're thinking about those training elements.

They're part of that success, and enablement is also coaching them. “Here's the metric of the baseline, and here's what we're trying to achieve. Please help us track and share any progress made each month so we can voice that up the chain as well.” 

It involves defining the metrics while ensuring many people are involved, apart from tracking and ensuring the success of those programs is being fulfilled.

The leading metrics to focus on

Something I've recently started is aligning with OKRs (Objectives and Key Results). I have specific initiatives that are part of individual sales leaders' OKRs for the quarter and the second half of this year.

For instance, our SME team was struggling. The sales leader in charge of growth for the Americas included me in their OKR setting for the second half of the year and this quarter specifically. So, I have specific goals I need to achieve for that team.  

Suppose you're tied down to a specific sales leader and are responsible for a particular initiative. This will have a direct impact, which you'll be measuring. It involves putting yourself on the line and is critical for collective success. Further, you get buy-in not just from the top level but from all the way down

If you have never done anything like this at that level before, it will be quite an experience. Maybe even a little scary because you have to rely on numerous people to make this metric come alive. But if you do it well, you'll ultimately have great success. For instance, you are redefining the buying personas in your Ideal Customer Profile (ICP). It requires a lot of testing. 

The outcome for the individual sales rep is better clarity about who they should be selling to and the specific messaging required for those new ICP buyers. Such a consequence will have an enormous impact on their lives. 

Driving an initiative

It is vital to have change management at the heart of enablement. Enablers don’t just change a sales cycle; they ask for ingrained behaviors to change. This is a difficult ask from reps, especially from experienced sellers who have had success in the past. Because today, reps are finding it difficult to say that what they did in the past isn't going to help them succeed today and that they have to do things differently. 

It’s also important to not try and change multiple elements but focus on key behaviors. Enablers sometimes make this mistake in focussing. It’s not just about spreading yourself too thin, but your focus is also getting spread too thin. This leads to not being able to give adequate attention and effort to each initiative to find success despite being constantly busy, leading to an underwhelming impact. 

Enablement’s focus needs more focus!

Everything you do should be geared toward how to get sales reps to change their behavior. Change management needs to be at the center of everything enablement does. If you're not already practicing change management, start by choosing one of the sales management philosophies. Study it in-depth and incorporate it into how you build enablement programs.

While you must be an expert, it's not enough to be an expert in only enablement. For instance, you may have a lot of certifications in several methodologies. You have to know how to roll out enablement programs. However, are you an industry expert? Are you an expert in all the different competitors in this space? Are you an expert in the product? 

Here are some of the aspects you need to be on top of to understand the revenue impact when you release a product:

  • Understand the product in-depth
  • Keep track of the calls you're listening to
  • The struggles the sales team is facing
  • The number one request they are getting from customers and prospects 

Knowing the impact of a product release and communicating it clearly to the sales audience will show a shift in the industry, the competitor, and the product. This will help arm reps with the top tracks that will be powerful to their prospects and customers. 

Often, enablers are only experts in some aspects of the business. However, moving forward, that needs to change. When you are seen as the expert, it becomes difficult for the organization to lose the expert. 

Changing the enablement narrative

It's a shame that many enablement folks are seen as trainers or simply there to onboard new employees. Several enablers today are sales experts, but they are getting pigeonholed into onboarding. With hiring not happening as much as before, enablers can now attach to specific coaching programs that elevate individuals or particular stages in the sales cycle. For instance, if an entire team is struggling in the XYZ area. Enablement needs to work towards addressing challenges that are preventing revenue growth.  

During the current economic landscape, when salespeople feel defeated due to difficult decisions and workforce reduction, maintaining a strong culture is critical. Enablement is central in telling reps, “We can do this, and this is how we are going to do this.”

If you've been in enablement and haven't played a critical role in the sales culture, that is a miss. Enablement needs to be a positive presence, helping to keep motivation high and ensure that the field is willing to go along with you to improve continually.

Enablement will fail without the buy-in of the entire sales audience. While that's complicated to put ROI on, it's highly critical. For instance, I do this by finding someone who's well respected on the team, is doing well, and they are part of my initiative. They're helping me voice and show what great looks like. 

If you're not including the top sales reps throughout the organization and sales management, then your power to be a part of that culture and to impact the sales culture is minimal.

The road ahead for enablement

Lately, there have been many signs that enablement is being leveraged strategically. Even sales leaders I've worked with who hadn't previously invested in enablement are changing their stance. 

The future of enablement requires us to possess expertise and lead projects in a way that ushers in change throughout the organization. This requires being very adept at ensuring every program you launch has change management built throughout to deliver an inspiring message.

The most pivotal element for enablement right now is to align not just to the top level but to every single sales leader within your organization. Enablement needs to be tied at the hip to their goals, their objectives, how they're being measured, and being of support.

How does AI affect salespeople today, and how will it affect salespeople in the future? Knowing how we should leverage AI and do it well is essential. That will allow us to do more with less. 

Whether AI or any other topic, the second something becomes mainstream or a buzzword, let's not just treat it as such. Enablement, instead, needs to become experts before anyone else, help institute it within the organization, and drive the adoption. This will allow sales reps to be successful in the new world of AI or whatever is next for all of us.

About the author


Jennifer Dougherty

Jennifer Dougherty is the Head of Enablement - Americas at Airwallex.

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