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Enablement Half Year Review – What are the experts saying?

As we all know by now 2024 has been a somewhat unique time for the world of B2B sales and sales enablement has become a crucial component for driving revenue and growth whilst ushering in changes.

It has been a fascinating year for enablement, marked by significant technological disruptions, particularly in AI, which is transforming traditional enablement practices. Coupled with a challenging economic landscape, these changes have prompted us to explore how experts are navigating these unique times.

To understand the current state we reached out to enablement leaders in the B2B space from prominent and innovative companies such as Expedia, Oyster, RingCentral, Pinecone, and Adobe. These experts shared their experiences and strategies for navigating the challenges that 2024 has presented from an enablement perspective.





Stephanie Middaugh is the Head of Enablement for the vector database organisation Pinecone. She also runs her own enablement consultancy called Phoenix GTM. In 2024 Stephanie released a book called Elevate and Optimize: Your Enablement Maturity Journey which is available on Amazon. Stephanie has a vast and varied experience in the world of ennoblement

How have your sales training and development programs evolved in 2024?

The market in 2024 is likely one of the hardest that many of our sellers have ever encountered. Buyers are more educated, under more scrutiny, and have less budget than ever before. In order to truly enable and train our teams to have effective conversations and run a good sales process, we can’t rest on the best practices that worked in better markets.

For me, I’m working on staying closer to my Reps and understanding what’s really working and not working. Figuring out ways to surface best practices and genuine conversation and connection over a distributed workforce. In a market that moves and changes as quickly as ours does, one of the biggest impacts I’ve been able to make is to store and surface information for my teams first.

Then move to the next step of reinforcement of the items that will actually move the needle in a positive direction instead of trying to plan too far in advance or force them through some checkbox Enablement that won’t help them.

In what ways have your strategies for engaging with customers changed in 2024? Have you incorporated any new techniques, content or channels?

Our Reps are leveraging AI tools like ChatGPT, Claude, and Perplexity in order to more efficiently understand our Customers and what they care the most about. Using public-facing information that they can find, combined with how to position our product to most effectively address and speak to the challenges and pain they are likely experiencing right now.

That tactic, while not new or groundbreaking, by leveraging AI, becomes much less manual and time-consuming, thereby allowing our reps to be more productive and personalise at a larger scale.

What have been the biggest challenges and opportunities in sales enablement for your organisation in 2024?

For us, the biggest challenge is the fast-moving and changing market. We play in the Generative AI tech stack space and there is something new and groundbreaking on a regular basis. When I joined the company 11 months ago, our reps really needed to educate most of our buyers.

Now, more buyers are educated and it’s shifted into more of a consultative sale. So for me, from an Enablement perspective, it’s working to understand what I can, and should, develop for my teams that won’t immediately go out of date. While also being insanely protective of their time from internal and external noise.

What new digital tools or technologies have you adopted for sales enablement in 2024?

I am very interested in roleplay technologies that are leveraging AI to turn traditional roleplay exercises, into something genuinely useful for the teams. I have been most impressed so far with Luster, and am actively working through how to potentially leverage their technology and platform internally.

If you’re involved in the enablement community, you’ve likely encountered Malvina and her exceptional contributions in sharing her expertise. She is at the forefront of researching and discussing the constantly evolving field of enablement. Additionally, Malvina hosts an enablement podcast called “The Enablement Brew” alongside fellow sales enablement leader Carly Lehner.

How have your sales training and development programs evolved in 2024?
Currently, we’re focused on harnessing the power of AI to enhance course and content creation. It’s an exciting trend that we’re actively working on and looking at ways in which we can make learning not only more engaging but also streamline & save time on content creation from our enablement team.

In what ways have your strategies for engaging with customers changed in 2024? Have you incorporated any new techniques, content or channels?

Digital Sales Rooms have been a game changer for us in 2024. At the end of 2023 we brought on board Trumpet which is used in every single deal that an Oyster AE works on. We streamline all information for our customers in the digital sales room, making it a collaborative space for both our sellers as well as our prospects. It has truly changed how we run our sales cycle. I recently received this feedback from our Trumpet CSM “Wanted to drop a message as just had a call with a prospect who came to us after going through the sales process with Oyster! She was singing Oysters praises and that they were blown away by the Oyster deal room and sales process and how slick, seamless and professional it is. A real testament to the process you and the team have built there”

What new metrics or analytics have you put in place to measure success?

We now track our win rates against digital sales rooms that have been created for each deal that we have open. We have seen a correlation between deals won and pods that are associated with the deal. We are also looking at : deal duration, closed lost reasons (what is in our control), conversion rates at each stage & average deal size.

What have been the biggest challenges and opportunities in sales enablement for your organisation in 2024?

OysterHR operates in a very faced paced environment with regulations and processes constantly changing. One of the biggest challenges for us is ensuring the speed of change does not overwhelm our sellers. At the same time, ensuring that content and new pieces of information are consumed in a timely manner has been challenging. There is a bit of “learning fatigue” happening at the moment where sellers in particular feel overwhelmed with the numbers of things they need to keep on top of. The biggest opportunity right now lies in streamlining and revolutionising the creation and distribution of content within the organisation. We recognise the need to enhance the learner experience, particularly in a fully remote setting. Our focus is on finding innovative ways to improve content accessibility, engagement, and relevance.

What new digital tools or technologies have you adopted for sales enablement in 2024?

We brought onboard Trumpet, Gong Forecasting & Reachdesk and we are actively re-evaluating our LMS used across Oyster.

Ernst loves building high-performing sales enablement teams that deliver compelling and modern solutions for global sales and account management functions. His mission is to provide organisations with the resources they need to close more deals. He thrives in large organisations with ambiguity and complex sales cycles. The work Ernst and his global enablement team have been doing at Expedia has been both innovative and forward-thinking.

How have your sales training and development programs evolved in 2024?

We are starting to view training and development programs as a component to the whole enablement package that will work towards a business outcome. In the past we might have looked at just one metric (views, completions or course rating etc) as a measure of success. Today, we first ask – did we achieve the intended business outcome, and what components contributed to this outcome instead.

In what ways have your strategies for engaging with customers changed in 2024? Have you incorporated any new techniques, content or channels?

Conversational intel has started to appear across the sales workflows. This is helping us to understand more about our partners but also helps us shape content for the future.

What new metrics or analytics have you put in place to measure success?

We are more looking at metrics more holistically. Enablement is not just one “thing” it’s a mindset and a discipline that involves leaders, comms, training, sales materials, and competency building across the sales organisation. So we have moved away from the “one metric” and turned it upside down. Look at business outcomes first – if we achieved what we said we wanted to do, that means it’s working.

What have been the biggest challenges and opportunities in sales enablement for your organisation in 2024?

Ai is everywhere, and it might be called the same but each Ai is different. Giving you different insights, or results. It feels like we are in the era of VHS vs Betamax and there is not yet a single standard that helps enablement professionals.

What new digital tools or technologies have you adopted for sales enablement in 2024?

Conversational Intelligence.

Ben is the Senior Director of International Enablement at RingCentral, leading a best-in-class team that supports the growth and success of the global sales force. With over 10 years of experience in sales enablement, training, and consulting, he has a proven track record of delivering impactful and measurable results for clients and partners. Ben is also a generous contributor to the enablement community, always sharing insights, trends, and opinions on all things enablement.

How have your sales training and development programs evolved in 2024?

We have had to get a lot quicker and leaner and AI has been a huge help to us. From building templates for Outreach all the way to more detailed role-play situations this has been a bit evolution in 2024. We are also told to show our value more than ever before, which has been relatively easy for my team as we heavily built that prior to 2024

In what ways have your strategies for engaging with customers changed in 2024? Have you incorporated any new techniques, content or channels?

So using deal-rooms/pitches via Enablement tools is critical now, it’s sort of expected, email and InMail is useful but the response rates compared to say sending a pitch/deal room post phone call are far less. So phone is back at number 1 (if it ever left) supported by video based content via a landing page

What new metrics or analytics have you put in place to measure success?

Tracking usage and tying it directly to opportunities. Tracking number of demos and velocity metrics tied into programs on new products especially, that has been a big one for us. We have reduced the reliance on SE’s in early stages and we have seen huge quantifiable success from that. It’s a nice program that suits the ‘narrative’ of many tech businesses in 2024

What have been the biggest challenges and opportunities in sales enablement for your organisation in 2024?

One of the biggest challenges with all businesses in 2024 is they think “Do I need the Director+ Enabler” or could I hire someone with 1 years experience or no experience and could they use AI to just replicate that function. If that is a risk to your Enablement org, then you are not showcasing the Actionable Impact to Revenue that you can achieve. That being said there is a huge opportunity to train and nurture the new era of Enablers – which is exciting, if you can showcase that you are the person to develop these entry role enablers, then you are in a great spot over the next decade.

What new digital tools or technologies have you adopted for sales enablement in 2024?

Cognism (Hopefully) – is the only real new one

With 22 years of experience in the IT industry, Pooja is passionate about helping customers achieve their transformation goals. Throughout her career, she has worked across Asia Pacific, the Middle East, and Europe, focusing on uniting people and technology to drive sustainable growth and strategic impact.

As a dedicated coach, Pooja finds immense satisfaction in helping her coachees discover and harness their true potential.

In addition to her professional pursuits, she hosts a podcast series called “Coffee Collaboration and Enablement,” where she explores her passion for fostering innovation and collaboration within the industry.

How have your sales training and development programs evolved in 2024?

We have been more customer centric and impact driven at Adobe

In what ways have your strategies for engaging with customers changed in 2024? Have you incorporated any new techniques, content or channels?

We have shifted our product enablement to be more customer centric and aligned to our sales methodology and we have done the same with our sales training programs. We use Second Nature to review and assess the skills of our teams and their ability to deliver customer value. In addition, we also have a continued improvement process in place to design for better outcomes.

What new metrics or analytics have you put in place to measure success?

This year we have put in some effort of measuring business impact of programs. Depending on the program, these impact measures are baked in sales performance data.

What have been the biggest challenges and opportunities in sales enablement for your organisation in 2024?

We have several sources of data and one of of the key priorities is to make sure we are defining what the right set of metrics are that we want to use to measure impact. As an example, for new hires, ramp to productivity is one source of data and time in role is another that we look at. For sales managers we look at behavior changes as well as performance against KPIS.

What new digital tools or technologies have you adopted for sales enablement in 2024?

Second Nature

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