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Episode 8: The Evolution of Enablement Maturity

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Shawnna Sumaoang: Hi and welcome to the Win Win Podcast. I’m your host Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully.

Enablement as a business function has evolved significantly in recent years. Alongside this evolution, the push towards enablement maturity has become all the more prevalent with recent research from Sales Enablement PRO finding that 48% of enablement teams are moderately mature while just 1% are among the most mature.

So how can you improve the maturity of your enablement function as the field continues to rapidly evolve? We have invited Highspot’s very own Vice President of Revenue Strategy, Haley Katsman, to the podcast today to help us answer just that. Thanks for joining Haley, I would love for you to tell us about yourself, your background, and your role here at Highspot.

Haley Katsman: Thank you so much, Shawnna, I’m excited to be here. Hi everyone, my name is Haley Katsman and as the vice president of revenue strategy at Highspot, I lead enablement operations and analytics and planning for our global go-to-market teams. In addition, I lead our company’s account development team focused on pipeline generation. I’ve been with Highspot for almost eight years which is pretty crazy and have built and scaled our revenue strategy team including enablement from zero to about 90 people in the past four years. We have gone through our maturity journey as an organization and I’m excited to talk through that with you all today.

My background is in marketing sales from several different fortune 500 companies spanning consumer products, commercial real estate, marketing, and advertising, and my passion is really building and developing high-performing teams, empowering next-generation leaders, and really solving complex cross-functional problems with data-informed solutions.

SS: I’m extremely excited to have you here Haley. We’ve worked together for several years now and throughout your years in the enablement space, I would love for you to share with us the evolution you’ve seen in enablement and how you’ve seen the space mature over the years.

HK: Well, as you know, we were in it together but when I started at Highspot back in 2014, enablement was a relatively new discipline. That’s not to say that someone in the organization was not doing enablement activities like a manager coaching their reps or someone running an onboarding program or telling reps how to use content, but in most organizations, it certainly wasn’t a dedicated function with a seat at the table in driving strategic initiatives within the organization. We’ve even seen the title of enablement become significantly more prevalent over the past 5 to 10 years and now you see companies like Salesforce, Amazon, Siemens, Twilio, DocuSign, and Airbnb with dedicated and quite large enablement teams with very senior leaders that have a seat at the table and we just didn’t see that back in 2014.

The evolution of it in the past few years, enablement has become so much more than managing content or training reps. The best of the best, some of the companies that I just mentioned are now really aligning go-to-market teams to systematically enable their reps to execute against the behaviors and initiatives that are going to drive specific outcomes that align to revenue target and that’s a different way than thinking about it from just, you know, have my reps gone through 100% completion of a particular training course.

I kind of like to think about the sports analogy, you can pick your favorite professional sports team, and in pretty much every scenario that team not only has a coach, but they have an entire team enabling their success. They have a nutritionist, a personal trainer, a therapist, a doctor, coaching specialists, and analysts that are systematically determining what’s going to make them most successful in winning a championship and they just couldn’t do it without that team. That’s really how I’ve seen sales and revenue teams evolve you can’t just bet on a few top-performing reps that have a book of business or relationships that they’ve been depending on for many years, you have to invest in enabling the team, and have to have a strong team of people that are doing that.

SS: I love that perspective on the evolution of the enablement market. Now, from your perspective, what is enablement maturity and what does that mean for enablement success within an organization?

HK: From my perspective, enablement maturity is shifting from the foundational programs to driving strategic outcomes that are again tied to revenue. For example, foundations are critically important, so it’s not that you don’t do them, enablement must lay that foundation for reps to be successful. Think onboard, sales methodology tools, enablement content, and messaging enablement. email templates, territory planning, you name it, all of those things are foundations to the business, but for enablement to truly be successful in an organization, I think it means three things. I think it means moving the maturity to become more granular and targeted to your approach with specific internal audiences and what they need to do to hit their quota targets. Second, I think it means aligning those foundations to specific business objectives, not just an onboarding program where you learn about everything, but what the rep needs to be successful in the first 3 to 6 months of their ramp to generate the pipeline needed to hit their targets as an example. Third, giving up the maturity model means becoming more data-informed and leveraging analytics to really optimize your enablement strategy and ultimately the business strategy.

Honestly, if I think back to 2014 that probably wasn’t possible because we didn’t have the data at our fingertips or the knowledge in which to know how to use it like we do today. I think that those three things, getting more granular and targeted, aligning to specific business objectives, and becoming more analytical and data-informed in your enablement strategy make the difference between a successful enablement team that has a high ROI and impact on the business. versus one that is still in its early days and focused on laying the foundation.

An example that may bring it to life is let’s say that your business determines that to grow the business and remain competitive in the market, they need to acquire another company. Super common. In your revenue model, there’s now going to be a line item associated with the revenue expected to be brought in via that acquisition. Of course, you’re gonna spend likely millions of dollars acquiring a company and there’s an expected revenue return on that. Now, we know that most strategic initiatives fail. On average, 70% of them fail and acquisition specifically more than 80% of them fail. The question is why. When you get into the execution of it selling this new product that’s been acquired, why would a rep go out of their way to sell a new product that they don’t know about, there are new competitors, and they don’t know what good looks like and they might already be hitting their quota without selling this new product?

Typically, organizations will build a ton of content, throw it over the wall, spend our certifying reps in a siloed environment and then months later find out that they missed the number for the acquisition. Well, if you think about enablement and moving up that maturity model, what if you had a systematic way to ensure that sellers achieve mastery of the activities or the behaviors needed to sell the product from this acquisition, and what if you had leading indicators to understand if you were going to miss the revenue number before you missed it? That’s where I think enablement can have a major impact on revenue. Those leading indicators to us understand, well, if we acquire this product and the reps don’t know about the product, they haven’t gone through the training, they’re not running the plays associated with this acquisition, well, I can tell you right off the bat, you’re probably not going to hit the revenue number.

It’s that transition from enablement, thinking about completion or attendance metrics to thinking about driving consistent performance so that you have most of your reps hitting quota and that quota is associated with the outcomes that you’re trying to drive throughout the business, such as selling this new product via acquisition, as opposed to just hoping that 20% of your reps carry 80% of the revenue. Making that mindset shift and really changing how you run your programs based on that, is that shift that I think enablement really needs to make in order to truly be successful.

SS: I love that perspective and thank you for walking us through that scenario. Now, I know it’s a podcast so unfortunately, we don’t have visuals, but at a high level, can you walk us through the different stages of enablement maturity and how have you experienced these different stages throughout your own enablement career as the field has evolved?

HK: At another time I could go much deeper on the five stages of enablement maturity across different areas of the business, like training maturity and content maturity and all of that, but just to simplify it down, I think that organizations go from being relatively unstructured and reactive in their approach. They’re kind of putting out whatever the most recent fire is, just focusing on those foundational programs like I mentioned, like an onboarding program and as you move up the maturity model, it really becomes more focused on what you need the reps to be able to do in order to hit their quota and for the business to hit their revenue targets. What that transition is from that passive reactive mindset to really start with what are the outcomes that we need to drive from a business standpoint and what are the behaviors that the reps need to accomplish and flip that on its head so that enablement has a way in which to prioritize the millions of things that the business is asking them to do by focusing in on what’s most impactful for the reps to be successful.

You’ll see from an enablement maturity standpoint, going from that unstructured environment and unstructured kind of way of working to being very value-driven, and everything that enablement does need to be tied to specific business outcomes. I’ve seen this come to life in our organization as we have evolved and as the enablement discipline has evolved from just like I said, being much more reactive to whatever is going on in the business and the most recent fire reprioritization that’s needed to happen to really shift where enablement is actually driving the alignment between the go-to-market functions and we’re giving early leading indicators to the business if we’re going to hit our revenue targets or not, and giving that feedback loop to say, hey, this initiative isn’t performing the way that we thought it would or it is, but not everyone is doing it and really able to course correct before we drive off a cliff as it relates to a specific initiative that we have.

That has just really transformed how everyone in the business engages enablement because we’re all working towards one common goal as opposed to having competing priorities and having re-prioritization of everything that we’re working on on a monthly and quarterly basis. We have a long-term plan and we’re working towards that long-term plan.

SS: Now, as advice to our listeners, in your experience, what are some of the first steps enablement practitioners should take to begin to improve their organization’s enablement maturity?

HK: I think there are two things that I would say. As an enablement practitioner, a big part of what we have to do, and I talk with people about this all the time, is we have to be selling enablement internally in our organization all of the time. It’s not the case that every CEO or CRO truly understands the value that enablement can provide and to assume that they do is just not going to help you get to that next level of maturity. I think first and foremost it’s identifying who are the key stakeholders that really need to understand what the value of enablement could look like within your organization. It doesn’t mean that you need to do it tomorrow, but helping them understand that if they partner with you and they make the investments, this is where the enablement function could go within your organization, and here’s how it would positively impact them and their world.

For example, for a CRO, I can help reduce rep attrition, I can help you improve your participation rate, and make more of your reps hit quota. I can help give those leading indicators to understand if you’re going to miss your revenue targets, those are things that they’re going to care about, and again, it doesn’t mean that you’re going to do them tomorrow, but helping them understand what enablement potential looks like will help you get them on your side of the table so that you can better partner with them and begin that enablement maturity.

I’ll also say that a really important step that I always guide enablement practitioners on is really understanding your revenue model. If you want to go and have a conversation with your CMO, CRO, CEO, CFO, or whoever that is to get buy-in, if you’re not speaking their language and understanding what business outcomes you’re trying to drive, they’re not going to take you seriously. You need to understand what the reps quotas are, what your headcount model looks like, at a very high level to the information that you’re able to get, what your revenue model looks like and what are the key strategic initiatives that your organization is investing in for you to hit those revenue targets. Oftentimes it’s not the case that they’re going to come and just volunteer that information to you and so you need to go out and seek out those answers. Sometimes they’ll openly give them to you or just get as much information as you can so that you can align your strategy to those specific metrics in the organization and they’re going to be much more inclined to have a conversation with you about forming a better partnership.

SS: Absolutely. Now, as you mentioned, Haley, evolving from one stage of maturity to the next does not happen overnight. What might a roadmap to maturity look like for an organization and how can teams develop that roadmap together with their stakeholders?

HK: I think the first and most important thing is getting a baseline understanding of where you’re at today and then where you want to go, and in what time frame. I think about that again, like let’s understand the current state where we’re at, where the gaps are and where we want to be call it a year, two years from now. Based on the gap between those things, there’s a set of things that you can do to help crawl, walk, run your way to that longer-term vision. We have something at Highspot called the strategic enablement framework with a set of maturity models, whether it’s your training maturity model or your coaching maturity model that really helps you go through that kind of crawl, walk, run process, but the most important part is getting an understanding of where you are today and where you want to go longer term so that you know what you’re working with.

SS: Absolutely. Now, Haley, one of the things that I’ve always admired about you is you have an extremely proactive mindset. What is the value of having a proactive mindset as an enablement leader versus a reactive mindset, and how can this help the journey toward improved maturity?

HK: I think of having a proactive mindset as looking around corners. Taking that initiative where someone might not have delegated or asked you to go and do something. I think that when you are able to look around the corner and be more proactive, what ends up happening is the business starts to look at you as more of a consultant and a strategic partner and they pull you into conversations more than you have to push your way in. What I hear from a lot of enablement practitioners is frustration and I 100% empathize with that because they’re not sitting in the room when the strategy conversations are happening and then they get delegated something and priorities change every seemingly five seconds, but probably, 3 to 4 times a year. The way to really flip that on its head is to be more proactive and help your stakeholders look around the corners and then like I said, they will pull you into conversations and that’s when you’re doing it right when you don’t have to push your way into the room, but when you’re being pulled in, but you’ve got to show value.

I think that the more that you can be looking around the corner and be proactive, the more value you’re going to be able to provide. The beautiful part about enablement is that it’s one of the only functions in the go-to-market organization that has visibility across the entire funnel and understands what’s working and what’s not working between all the revenue-generating teams, because oftentimes it can be relatively siloed. You have this amazing and unique perspective to share that proactive looking around the corner, those insights, whether they’re analytical or whether they’re more anecdotal. I think that you can really take those insights, package them up and help people look around the corner, and then you’ll get pulled into having a seat at the table as opposed to having to push your way in there.

SS: Fantastic. Maturing and enablement functions require a lot of change management. What are some of your best practices for driving change through enablement?

HK: I would say that change management is difficult but I think that one of the things that are incredibly critical in driving change management is getting alignment on the outcomes that you’re trying to drive. That goes back to what I talked about earlier around understanding your revenue model, understanding the key initiatives that the business is prioritizing to meet those revenue targets and when you’re able to align everyone towards a common goal and a common vision, then you’re able to enlist them all as agents of change in that process.

I think it’s really critical to really understand why the business is doing something. Let’s just take that acquisition example that I gave earlier. Well, why did we acquire that company? Is it because the product that we acquired is going to make us more competitive in the market, or is it because we need to increase our price and ASP and so we need to add more value to our offering? What is the why behind it, because then what you need to do from an execution standpoint, and really what the reps need to be able to do might be incredibly different depending on the why? Let’s say it’s because of competitive reasons, well then as it relates to that acquisition and that new product they’re going to have to really understand the competitive landscape and potentially new competitors that are coming into the deal and how to do objection handling and competitive daggers and whatnot. If it’s about increasing the value of the platform, they’re going to really have to understand value messaging and how to talk about the entire solution and the ROI of your solution, which is a really different thing that you’re asking the reps to actually go and do.

Oftentimes everyone has the why in their own mind and people have different opinions on it and that’s what causes that lack of alignment. Ultimately, if you don’t have alignment, it’s really difficult to drive change and so I think that as enablement leaders our job is to drive that alignment, and the best way to do that is to align the group to those outcomes and to the why behind those initiatives so that you know exactly what you want your reps to go and do and can really get everyone behind systematically driving that change.

SS: I love that now. Not that this is a sales pitch, but how can organizations leverage Highspot to help achieve strategic business outcomes through enablement?

HK: A lot of what we do with customers is of course related to our platform, but a lot of the conversations that we have with them are actually just about how to implement best-in-class enablement discipline in their organization. I think that there are things that we can do from a technology standpoint and then there’s a whole lot of things that we can do as it relates to advising and consulting on how to move through the maturity model, how to get a seat at the table, how to get more investment, how to become more data-driven in your approach, all of those types of things. I think at the end of the day what we really help companies do from a technology standpoint is we really help connect all of the dots in one unified place in which you need to drive that systematic change in behavior.

Instead of onboarding a rep in one platform, teaching them their methodology and another giving them content in another place, and trying to piece together all the analytics in a third-party data source, which is a complete nightmare, it’s not a good rep experience and ultimately at the end of the day, it’s not going to drive any change in behavior. What we’re really focused on is how we help that all come to life in one place where it’s a seamless experience, it’s in context, in the moment of action, and where all the analytics are already stored in one place that you can connect to business outcomes in your CRM. Again, I think there are a lot of advancements that we’ve made from a technology standpoint that unlocks enablement’s ability to be more data-driven and connect better to business outcomes, but at the end of the day, I really think that we’ve helped a lot of organizations move up the maturity model through our expertise and enablement, the best practices that we’ve developed, not just from our own experiences but from the experiences that our customers have had. We work with the best enablement teams in the world and have learned a lot from them and so that’s what really excites me about partnering with companies is really helping enablement get a seat at the table and help enablement make the biggest impact on the business as possible.

SS: I love that, Haley. Last question for you. To close, how do you think enablement will continue to evolve in the next year and beyond?

HK: I think some exciting things are coming. One, I think enablement already is but will continue to evolve beyond just enabling sales. I think it’s going to be about enabling all customer-facing and revenue-generating teams, pre, and post-sale, customer success, partner, marketing, and even evolving into enabling customers. It’s all about starting with the customer experience and with the outcomes that you’re trying to drive around revenue, and customer satisfaction, an enablement really should be taking an aligned approach to enabling anyone that touches the customer. I think that’s one piece, you’ll see revenue enablement as a new title that’s popped up over the past couple of years, whereas it used to just be sales enablement.

Another trend or evolution that I’m starting to see and really hope to see more of is manager enablement. I think historically enablement teams have been focused on enabling individual contributors, like reps, and if you have the business and an enablement team telling a rep to do one thing, but their managers coaching them on something different, who do you think they’re going to listen to? They’re going to listen to their boss. I think that we need to do a better job at really setting the frontline managers and even the managers of managers up for success and understanding exactly what their reps need to be able to successfully do to meet their targets. Manager enablement and coaching is a huge evolution that we’ve made ourselves and has really unlocked a lot of potential for us.

Then, I think this is kind of a specific one, but I really hope and I’m starting to see that enablement becomes model driven from a headcount standpoint. You get what you pay for back to that sports analogy and if you want a winning sales team, you need to invest in setting your revenue teams up for success. I hope to never see any more of these one to two-person enablement teams expected to enable thousands of people because I can just tell you it’s near impossible to move that far up the maturity model if you are not investing in setting your revenue teams up for success. I think the best way to justify that in the business is to make it model-driven just as you would with a sales engineering-type team, whereas in most organizations it’s very model driven based on how many reps you have. I hope to see the same thing from an enablement standpoint because that then is what truly will unlock enablement and thus the revenue team’s ability to perform at the highest level.

SS: That’s fantastic, Haley. Thank you so much for sharing your expertise and your experience in enablement with us over the years. I really appreciate your perspective.

HK: Absolutely! Thank you so much, Shawnna.

SS: Thank you to our audience for listening to this episode of the Win Win podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot.

Authors

Shawnna is Director of Marketing at Highspot Her background is in strategic development and execution of marketing and communications programs in the technology industry…

Haley leads growth enablement and growth operations for Highspots gotomarket teams…

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