According to a Harvard Business Review report, about 70% of change initiatives fail. So how can enablement help sales teams navigate large-scale transformations and come out stronger on the other side of change?
Shawnna Sumaoang: Hi, and welcome to the Win-Win Podcast. I am your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully.
Here to discuss this topic is Jenna Siegel, the director of revenue enablement at InMoment. Thank you for joining us, Jenna. I would love for you to tell us about yourself, your background, and your role.
Jenna Siegel: Thank you so much for having me. I’m excited to be here. I made a large shift to land myself into enablement. So I came actually from an academia background, teaching at the University of Illinois Chicago, while I was working through some postgraduate work, and I quickly realized that academia wasn’t a place that I wanted to land for the long term. Which left me with this really kind of humbling experience of what do I want to do with my life. And I think like many people in enablement, I landed myself in sales. I was in various go-to-market roles, whether that be service, sales, or customer success, and I really quickly got frustrated with like, the lack of resources and education in the corporate space. And of course, as someone who came from an education and academia background, I was a constant advocate for we need resources to get everyone to speak the same language, to get everyone to understand the same processes. So after having worked in go-to-market roles for several years, I landed a role within enablement and I’ve been there ever since for about six years now.
SS: Jenna, we’re really excited to have you here on the podcast. So thank you so much for joining us. I know your team recently went through an acquisition, which can often bring significant change for sales teams.
What best practices did you implement to help your teams effectively navigate through this transition?
JS: Absolutely. So acquisitions are so tricky to navigate and I really feel like they’re fear-inducing for everyone involved. So with my team, I was leading revenue enablement at a company called ReviewTrackers that was acquired by my current company called InMoment.
So ReviewTrackers was a really small organization with a very small enablement org. InMoment was actually a much larger organization without any true dedicated revenue enablement. So for us, it was so easy to step into this expanded role of leading enablement across the entire organization with truly preconceived notions of what we thought would drive success, mainly because we knew what drove success at our small little scrappy company called ReviewTrackers.
So the biggest challenge for me and for my team post the acquisition was really just to be curious. Right. We constantly are preaching this to our sales reps throughout the discovery phase. Be curious, ask a lot of questions, and really learn about them and their business. And I think we often forget to do that in enablement. We come in and we’re like, I know what drove success. I know that doing this sales methodology is going to work because look at the success it drove for my prior business. So we really had to adopt the same methodology in our transition. And this didn’t just involve meeting with the stakeholders and with senior leadership and presenting our expertise and our plans and getting their feedback, but I think the most important thing that we did was really step into meeting with the frontline folks, those that are executing on the role day to day and really learn about what are their challenges, what are their enablement desires, what do they wish they had, but Had never had because they didn’t have a revenue enablement dedicated role.
So it was a new function to in the moment and we stepped in and I think it was split. Some people thought, Oh gosh, these people are going to come in and they’re going to make our lives miserable and they’re going to implement all these trainings and we’re, it’s going to pull us off the field. You know, our biggest strategy in the acquisition was driving trust and confidence across our teams before we ever were able to present a plan.
SS: Well, it sounds like you guys did a phenomenal job really driving that trust and confidence across your teams. I know unifying the go-to-market teams is essential during these types of transitions. What challenges have you encountered in aligning your go-to-market teams and how did you overcome some of these challenges?
JS: Yeah, absolutely. So I think the biggest thing is we weren’t just unifying teams, we were unifying regions. So we had three separate regions that were functioning pretty independently from each other, as well as teams, whether that be sales, success, ADRs, or our account management team that were also functioning independently from one another.
And one of the first things that we identified was that there was a vast amount of technology and go-to-market processes that differed across the org, especially because of the number of mergers and acquisitions that they had gone through even prior to acquiring review trackers. And I strongly believe that these fragmented technologies and processes Also aid in creating a fragmented go-to-market organization.
So I’m so grateful that I sit under a really brilliant revenue operations team that I could partner with and they could partner with enablement. So we could really understand how the technologies and processes were being used and where there was room for optimization. This was really our first step in trying to figure out how we were going to unify the teams and how we were going to get everyone working.
Together and in the same direction. Don’t get me wrong. All these teams were doing really brilliant work, but it was very fragmented in nature. So in doing that, we explored how can we string together the processes and the technologies to drive adoption. So for example, we’re a MEDIC shop. Post acquisition, we implemented MEDIC methodology.
And I think it’s really common to introduce selling methodologies and send everyone on their merry way and just hope that it works. You know, we can implement it for sales, we can implement it for success, we can even implement it for our account management team, and I just really hope that they put it into practice.
But we had the really unique opportunity to rework the systems and the processes alongside introducing some of these new methodologies. So we were able to layer in, here’s the new methodology, let’s practice it. Let’s get it, you know, we know it’s not new to the go-to market organization. Here’s how also your technology is going to hold you accountable.
So this kind of set the groundwork for how we implemented our CRM system. How we set up sales stages with exit criteria, how we deploy information through the LMS system, and it can be role-specific, but the same line of thinking to all these different go-to-market organizations. How we set up Highspot, and how Highspot is organized for all of our sales reps to use, and our go-to-market orgs to use. That was our biggest thing to tackle when we thought about how we were going to unify the teams.
SS: Mm. Particularly in a merger acquisition, I know sometimes employees can feel uneasy as team structures and roles and dynamics evolve. What’s your best advice on motivating teams and reps in particular to really ease them into the process of change?
JS: Yeah, I think it all goes back to communication, right? We know it’s essential to get leadership alignment first. That’s number one. If leaders are aligned and bought into the changes and brought into the processes to help define the processes, we know it’s going to trickle down to their teams. But also, we wanted our frontline people to have a voice in these changes.
Silos, like especially for InMoment, we’ve seen this happen, can only bring about further anxiety and defiance and actually adopting the process and burnout employees. So we created these group of tiger teams, where we brought together leaders and individual contributors, and into these teams to help us define the processes, and poke holes through our processes.
And that trickled down to the greater team because they were bought in. They could be, you know, the leaders of their team. They can advocate for these processes and these systems. And that’s where we see the most amount of success and hoping that people aren’t anxious or hoping that people can process these changes.
SS: Yeah, I think buy-in is absolutely critical. From your perspective, what is maybe the strategic advantage of an enablement platform when navigating change like this?
JS: Yeah, that’s a great question. And I love enablement platforms. I’m a huge believer that even the smallest go-to-market org and the smallest enablement team, it’s very hard to be effective without having a platform in place.
I like to split this out into two pillars why we think enablement platforms are important or how we really use it to our advantage. One is how we deploy enablement. So how we even go about deploying enablement? The second is how we track the efficacy of the changes. And the efficacy of the enablement that we’re putting out into the field.
So, regarding how we deploy enablement. Our enablement org, here at InMoment, although it has grown since the acquisition, is very small and very scrappy. And we as a small team, need to be able to scale. And when I hear people say scale, my first thought is always, Oh gosh, everything’s just going to be LMS courses.
Nothing’s going to be live. We’re not going to have hands-on training. And I don’t believe that to be the case. I don’t think that scaling for our team means abandoning live training or completely avoiding the face-to-face aspect of enablement. I think it’s actually quite important in this kind of blended learning environment post-COVID and post-remote teams.
Deploying enablement for us means What is going to happen after we have run the initial enablement? I quote this study to like nausea with my team that 30 days post enablement, 70 percent of the content is forgotten if we don’t do any sort of follow-up. So we really like to use our systems to give those reminders, to make the content continuously reappear post enablement.
So maybe it’s using Highspot to actually send content newsletters. We deployed enablement. We know these are the pieces of content that really coincide with the enablement. We send monthly enablement newsletters actually using Highspot digital rooms, which people love so that it’s, the content stays front and center.
Or maybe it’s deploying an activity in our LMS system. Hey, we ran this enablement session. Here’s this quick activity or challenge that we want you to engage in. Or also maybe it’s gamifying it through our systems to make learning a little bit more fun. We recently did Highspot scavenger hunts post-enablement.
We launched a new product line. We had what we call expertise exchanges where we really shared best practices amongst the team. And part of that was a Highspot scavenger hunt of like, who can find the most relevant stats related to this product and related to the value of the product and share it with the larger team.
People loved it, right? It’s different. It’s not your typical sit in hour-long live sessions where we know that. 15 minutes in we’re losing people to their email and their slack or it’s not, you know, all of a sudden we’re opening up a breakout room on Zoom and we see the attendance drop 50 percent because people just don’t maybe have anxiety around that which is also understandable, but we also need to combat.
So this way of gamifying it through our systems and through our enablement platforms is really important. So that’s our first pillar. Our second pillar is how can we use our enablement systems. To measure the efficacy of our efforts. We deploy surveys. I didn’t mention this yet, but Amoment is a customer experience technology platform.
We’re really big on how can we understand our customer’s experience. And here in enablement, we think our customers are all the internal folks that are on the receiving end. Surveys give us really great feedback. But they only tell a portion of the story. We can get survey feedback that’s like, everything was amazing.
We love this enablement session. It was fun. I learned a lot. And then a month down the road, the data is telling us a very different story. And we really try to take a holistic approach to how we understand data. So if we run an enablement session on a product launch, anytime we run a larger initiative, my enablement team, we measure various data points to really understand where it is that we need to go next.
We can look at the lagging indicators, that’s like financials and deal velocity and all of that. But I think a lot of the really good information and the juicy information lives within our enablement platforms. You know, we include attendance and completion data point. There’s quite a bit that goes into the data that we’re looking at.
Conversational intelligence data, how they’re actually speaking about it in our field, but enablement metrics like Highspot metrics are really important to us. Perhaps it’s that we’ve deployed this enablement. We’re seeing a huge uptick in how they’re using the content. And then the next month, it’s not unique to InMoment.
We see a huge dip down and all of a sudden no one’s using it. Well, that tells us we need to resurface this in some way, shape, or form. We need to figure out how we’re going to get people talking about this again. So it really is our signal for where do we need to re-engage and where do we need to re-evaluate our strategy.
SS: I love hearing that. Shifting gears a little bit, content governance has always been a big focus for you this year with 58 percent of InMoment’s content now well governed. Congratulations. How have you been able to optimize governance and what impact has this had on your team as they navigate change?
JS: Yeah, I strongly feel that we had a Bigger mountain than usual to tackle when it comes to Highspot, um, particularly because my team, again, there was an absence of a revenue enablement team at InMoment for a long time, and my team acquired Highspot, and it was a tool that was launched out to the masses without any real strategy around how it was going to be maintained.
So when we acquired Highspot as a team, we had a lot to tackle. One is that there was a lot of outdated content on there. I think I found content back from 2009. Which is problematic and also just unnecessary because Highspot provides the governance tools that you would need to make sure that content is refreshed.
So when we had initial conversations with our go-to market team, when the acquisition happened, I said, how are you all using Highspot? The number one answer is, Oh, we don’t look in there. There’s too much outdated information. So my team started by doing a content audit.
We pulled a list of all of the content that lived within Highspot, with how many views it had. We really used the data in Highspot, how many views it had, when it was last viewed, when it was last updated, when it was originally uploaded.
Unfortunately, nothing had feedback owners listed on it. So we really didn’t even know who owned the content outside of original authors or whoever uploaded it originally. So we, as an enablement org, had our product marketing teams and our marketing teams go through an exercise of marking content as.
It’s outdated, remove it. It’s still relevant content, but needs updating or it’s good to go and keep it as it is. In doing that, we got our content down to, I want to say about 400 to 500 pieces of content from thousands and thousands of pieces of content, which was really big. Our next step was actually working with our go-to-market teams and creating a tiger team to figure out how do we want this organized in the system.
People did not know the searching functionality well enough to be able to find the information they needed. And there were no logical spots set up in the system where they could just click in and say, Oh yeah, I’m looking for a pitch doc, so I’m going to click here, or I’m looking for a blog or a gated asset, I’m going to click here.
So we worked with the various different go-to-market teams, customer success, sales, ADRs, to figure out a unified way of organizing the content within a system with the relevant filters. We know our ADRs want to filter by buyer persona. That’s how they’re going to market. And that’s how they’re prospecting.
But we know that our customer success folks might not want to be only filtering by buyer persona. So we created what we think are very logical spots with the appropriate filters for the appropriate teams. And then I think the most important piece of this is that every single piece of content is required to have a content owner, a feedback owner so that people know if there is an issue with the content, it’s not a giant hole in the system where you’re just stuck with this outdated pieces of content.
You have someone that you can go directly to and say, hey, this isn’t up to speed. This isn’t landing in the form. Or this has a customer who’s no longer a customer and therefore we need to take it out. That was a big piece of the puzzle as well as putting expiration dates on everything. So everything has a six-month expiration date at the six-month period.
The feedback owners can review the content, mark it as still applicable, or say this needs to be removed off the system to make sure that we never get into the state that we had before. And also just a big shout-out to Highspot on that one. That was a massive undertaking and a huge project which the Highspot team helped us out on a weekend when we took the system down. They were just Malcolm, our customer success rep. He was really there to help provide us with industry best practices. I don’t think we could have done it alone and in a silo.
SS: Well, I love hearing about project wins like that. In a recent webinar, you actually mentioned that your team holds monthly expertise exchanges to promote peer learning.
Could you share more about this practice and how you foster a culture of ongoing learning?
JS: Yeah, our expertise exchanges were created because when we stepped into the role, there was a lot of silo work going on, and we knew that enablement was never going to be effective if we did a one-and-done approach.
So we created a series of expertise exchanges. We’re on a monthly cadence. We get together the various teams and we really take a look at, well, what enablement did we run this month? What was our focus? And it leaks over month to month. For example, if we’re running product training, And then we’re also running a methodology.
We try and blend the two together to really make it a holistic training that the enablement efforts aren’t even siloed within itself. Every month we look at what enablement we run? What data were we trying to influence? And we figure out a theme for our expertise exchanges. So, for example, one month that theme might be a product line, right, reputation management in the field.
We assign them through our LMS some pre work to do prior to these expertise exchanges so everyone comes prepared. That usually is, for example, uploading a prospecting email that you sent and then post the enablement session or providing a pitch deck or a recording of a call. We try to make it things that they’re already doing.
So it’s not seen as, Oh gosh, I have to go do a mock demo or I have to create a fake pitch deck. We want it to be things that they’re actually doing within the field and it shouldn’t be a lift for them. And it’s also not a lift for enablement. It’s an easy one for enablement. Enablement reviews. Those we come together as a go-to market org.
And we just call upon people. Hey, I know you all have been putting this into practice, would love to hear where you’re seeing wins, where you’re not seeing wins, and really just share amongst each other. People are very eager to share their wins, which is great. So very rarely do we have to call upon people, but we also have the submissions in advance so we can take a look at them.
And if we have that moment of like no one wanting to share, call out their wins for them, right? Like, hey, I saw Caroline, that you worked on this email that actually. Our outreach data shows got 40 percent reply rate to, can you talk about your email? It’s a really great way to get people to see how they’re actually putting the enablement strategy into practice in the actual field.
And also we just create a library for them in Highspot as well of like, here’s the examples of when so you can easily find them and go off and do the same. If someone else is seeing success, you should absolutely adopt that and you should absolutely put it into practice yourself.
SS: I think that’s fantastic advice that our entire audience can maybe even take and apply in their organizations. As you’ve expanded and evolved your enablement strategy, what key metrics would you recommend tracking to effectively drive change?
JS: Yeah, absolutely. I’m sure everyone preaches this, but I really do sit under the most brilliant revenue operations team and most brilliant revenue operations organization, which is great because I have access to all the data that I could ever possibly need.
And I think like many enablement leaders, I bucket our metrics into leading and lagging indicators of success. And leading and lagging indicators of influence, which I don’t think is a unique model to be using, but it’s a very effective model. So the leading is the data that myself and my enablement team, we can directly tie back to our enablement efforts.
Things like attendance and completion rates and challenge scores, and even conversational intelligence trackers within our CI system. Those are really easy metrics for us to. Be able to track to start to tell part of the story. I think the lagging indicators are so important to prove our value to the larger business and to continuously show how we are aligned with whatever it is that the business is trying to focus on.
And those lagging indicators are ones that we would also love to be like, yes, enablement. Had a direct influence on, but there’s other, you know, influences that come into play there. I often find that those lagging indicators are the hardest. Bits of data to get access to in the business. But as I mentioned, I have like the greatest revenue operations team.
And specifically, I have a colleague on my team, a coworker, Trevor, who builds out the most brilliant lagging indicator dashboards. He even does a good job of like bringing in the leading indicators to that dashboard. And this is what we really use month over month enablement strategy. So these are things like deal velocity. These are things like the financials of like, if we’re doing enablement on a specific product line, are we seeing an uptick in the revenue that’s coming in from those product lines? Our pipeline data, even outreach data and data specific to our tools. We really deep dive into this data month over month.
And we actually have like a monthly data review session where we look at our leading indicators, lagging indicators, try and drive correlation, but also. It’s not just for proving out the efficacy of our efforts. It’s really figuring out, okay, based on this data, where is it that we are going to go next?
And I think when we’re looking at data, we do it in two ways. One, we have quarterly priority sessions amongst my enablement team, where we all sit down and we figure out, okay, what are the biggest like lagging indicator data drivers that we need to have influence on this quarter? What’s data telling us?
Is it retention? Is it pipeline? Whatever that is. And then month over month we look a little bit more granular at the data to figure out are we actually having the impact that we need to have. From a business perspective.
SS: I think those are definitely some of the key metrics as change efforts. Typically, though, they kind of progress through various stages and often require time to fully implement. How do you maintain momentum as new processes become solidified in the long term?
JS: Yeah, we love to take an ever-boarding approach. So we onboarding new people. We also do it when we’re launching large-scale enablement efforts. I actually think the key to making enablement sticky is providing leaders with the resources to coach on this on an ongoing basis.
We are a small team. We can’t scale to have on one conversations with everyone and figure out where it’s falling short, and where we need to make adjustments. Perhaps Mike is better than Anthony. We don’t have those resources to be able to get really granular into the people aspect of this. But the managers do and that’s their job and they want to be doing this.
So we like to think about when we launch an enablement series, Look at the data first. We figure out why are we doing this enablement. Is it necessary? Are we doing this because we have our own agenda or does the data align with us? We then meet with the managers first and we actually run almost the same version of the enablement session with them with some caveats why are we running this?
What’s the purpose of this? What are we going to be presenting? And then the last part of that is managers, what do we need from you post enablement? Maybe it’s that we need you to listen to one call per rep per month and provide them feedback in the system so that we can gather that data and see how this is sticking.
Maybe it’s that we have created a coaching template so that you can have these conversations in your one-to-one. And by the way, upload those into one of our systems, obviously on a private basis, so that we can review those as well. We want to be able to provide the leaders with the resources that they need to help us make enablement sticky.
And then we run the enablement session for their people. And then when we’re doing the expertise exchange, we also have a one-month retro with the leaders where we talk about what are you seeing in the field. What’s working? What’s not working? A very similar exchange session that we do for our. People but with managers. We want the managers to have a voice in where we go next as well.
SS: I love that. Last question, Jenna. Looking ahead, how do you envision evolving your enablement strategy to keep pace with your business’s growth?
JS: Yeah, absolutely. We actually just had our enablement strategy meeting for 2025 and really starting to look at the data.
And actually, as of recently, my team acquired product training as well. So we now have an even better opportunity to kind of align all training across the business and make sure that we’re all working in a singular direction. Although for a lot of new teams as well too, right, we’re not just focused on revenue enablement now.
We’re also focused on the technical teams from a product training perspective. So, alignment across the org and how we approach enablement. I’m also selfishly very excited about this because I get a lot of new unique perspectives from my team considering I have new folks on my team now as well who have had a different view vantage point of enablement across the org.
But also I want my team to continuously get to a proactive state. And I think we can only get there by being brutally honest about our current progress and using data to drive decisions. I love what my team has done thus far in using data, but The data is one piece. We need to storytell with the data.
We really need to make it make sense for everyone else within the business. And we need to make it make sense for us so that we can be proactive. We have like one rule on my team and it’s, you’re not allowed to bring an ego to work and think that your way is the best way. And during our enablement strategy meeting, I started off with everyone needing to challenge us, and challenge me as a leader.
I don’t know the best way forward all the time. You all have great ideas that I have never even thought of. We all need to continue to challenge each other, use data to make data-driven decisions, and really continue to retro and think about, did this work? Was this effective? Was this not effective? All while being proactive and really, you know, scaling our team.
It’s like an impossible task that we have as enablement, but I think it’s possible with the right people and with the right strategy.
SS: I’m excited to see where you all go. Thank you, Jenna, so much for this.
JS: Yeah, thank you so much for having me. It was great.
SS: And 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.
