Shifting Enablement Strategies to Optimize Rep Engagement

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

Here to discuss this topic is Heather Green, the Director of Enablement at Jellyvision. Thanks for joining us, Heather. I would love for you to tell us about yourself, your background, and your role.

Heather Green: Hi, thank you so much for having me, and absolutely. I started my career in an individual contributor role in sales and worked my way up through sales leadership, but quickly found my passion for enablement early on.

I’ve worked for small startups to multi-billion dollar consulting firms and through it all, I consider myself to be a bridge for the sales organization. In my current role here at Jellyvision, my goal is to provide our revenue team with really everything that they need to be successful, from net new business to retention, and that’s through our direct channel and partnership business. So my team works to bridge the gap for our revenue teams. Marketing, product, and operations and support our sales team in any way we can.

SS: You mentioned you have an extensive amount of enablement experience. What are some best practices you have when aligning your enablement strategy with the strategic initiatives of the business?

HG: Yeah, it can be a challenging one sometimes. I would say hands down building internal relationships with our business stakeholders is incredibly key to bridging those two gaps. Everyone has the ultimate goal of providing revenue at the end of the day and making us profitable, but each team has their own goals that might not overlap with each other.

I found that it’s really important to have consistent transparency and ongoing communication to make sure that I’m working with these teams in tandem which causes minimum confusion at the end of the day with our revenue teams. So a strategic initiative could be launching a new product or feature, but then that could be in peril with another initiative that RevOps is perhaps launching something new with this system, so it’s too much at once. It’s really important that we get that buy-in from our leadership teams across the organization to make sure that everything from a product launch to new rep tech, to a marketing campaign, that it’s all working cohesively together.

SS: That is amazing. And you did mention though, that it’s not always easy. What are some of the major challenges that you’ve come across in your career when it comes to effectively really bringing your enablement strategy to life?

HG: It can be tough sometimes. There are definitely challenges associated with it, but where would the fun be if it was so simple all of the time?

So, especially when it comes to enablement initiatives, it’s so very important for me to make sure that our leaders understand the value of the why behind the initiative and the what’s in it for me for the individual contributors and ultimately what our goals are going to be at the end and what everyone’s going to get back.

By getting that leadership buy-in, we can get everyone on the same page. It’s oftentimes an uphill battle but I’m a big fan of throwing on my hiking boots and climbing, right? So each step when we’re rolling out a strategic initiative it’s a long-term play. It’s not a short tactical thing. Each step is learning more about what’s important to each leader and then how we can pivot and adjust to best meet their needs to make sure that we push it forward.

SS: I love that analogy, too. Now, when you first joined Jellyvision, you noticed some key challenges with the team’s previous enablement platform. What were some of those challenges and what was really the impetus behind deciding to make a change?

HG: Other than me adoring Highspot, right? I’ve been such a fan for many years and I was lucky enough to use it at other organizations. But coming to Jellyvision for me a few years ago, I was thrilled to see how extensively our team had invested in the tech stack.

A lot of times you don’t think many organizations. So as an enablement leader, it was just music to my ears, but with our previous content management system and engagement platform, the first thing I did when I came in was I looked at it and I did an audit. I’m looking at the backend analytics, but then really seeing

Who’s using it, who’s not, what the top performers were doing, what our lower performers in that middle ground were doing. The spoiler was that not a lot of people were using the platform, which, also hurts because as an organization, you’re making that investment and you need to see that return to keep it.

And so by digging in, I started doing many different conversations with our revenue team and individual contributors to determine. What was the reason behind not using it? And the key feedback that we received is that it was just difficult to use. It was hard to find content. It was even harder to edit content.

And so it was like, why would I do that when I can just go into my Google Drive and find what I need and then edit and send it that way? It was just resounding results that it was difficult and no one wanted to engage with it. But knowing the value of a platform like that, I was able to then start putting the seeds down for making a change.

I knew we were coming up on a renewal in the upcoming six months. And so I started asking additional questions on if it did this with this work and kind of planting the seeds. And then finally got to a pilot point of taking it with our key top sales reps and showing them what Highspot could do. And then from there, we were able to move the conversation forward in making the change once they saw some of the key things that Highspot was able to offer us.

SS: I think that is fantastic. And, in addition, I know that you did a lot of work to ensure that you had buy-in from leadership to prove why the change was needed. What were some of the things that you did to ensure that you were able to secure that buy-in?

HG: Buy-in is imperative, right? Especially when budgets are tight and they’re getting tighter and tighter every single day. So for me, it was gathering all of that data from our reps. So not only the analytics in the platform that we currently had and how rough it was from an adoption standpoint but then the verbatims from our reps of saying, “Yes, if we could have a Digital Sales Room, it would mean the world because then I would be able to track with our broker clients or if I were able to be able to easily find something and edit it in the platform, I would use it.”

So I pulled together a lot of the verbatims and then I put together the ROI breakdown of what we could see in the platform. We were lucky enough in the business case I put together to start Highspot three months before our previous contract ended.

That way we could load everything into Highspot, and do a full content audit, so we were starting clean. That’s so very important too, because what you put in ultimately will drive what comes out. But that allowed us time to do that audit, load, and tag everything appropriately in Highspot. And so that way we had a really, and do enablement ahead of that as well, to start again planting the seeds that change was coming. And these are the cool things that you’ll be able to see with it for us to have that smooth transition once we ended our previous agreement. 

SS: And since you guys have implemented Highspot, how have you overcome some of the challenges that the teams were previously facing?

HG: Adoption can be difficult across the board, but with Highspot, luckily, our adoption has been significantly higher than what we received with our old platform.

For us, I think it was consistently highlighting what was working, what top performers were using, and what they were seeing off of it, being able to track it back to specific deal conversations, and how they were able to move those opportunities forward through the content they were sharing. We also hold bi-weekly office hours where we share our best practices.

And in those best practices, peer learning is incredibly important for us. Making sure that we’re sharing what’s working with our tools and oftentimes when you have one person see what someone else is doing and how it’s helping them, that also helps to drive it forward. We also offered consistent training from video courses to one-to-few to one-to-one sessions. Luckily we’re in a smaller organization where we can offer that level of support, but to make sure we’re overcoming any obstacles, if someone wasn’t using the platform, myself or one of my team members would reach out and say, “What’s the problem, what’s going on?”

Oftentimes, it was just that they were uncomfortable trying something new, but after we showed them or they spoke to a peer and we had that connection, we’ve been able to get a much higher adoption rate.

SS: Fantastic. And you guys do have incredible adoption. I think you guys are at about 89% recurring usage. What are some tips that you have for building trust with reps and helping them understand the value of the enablement programs that you’re delivering?

HG: It’s really due to my team. Shout out to Max Costello, she’s hands on our Highspot champion, and we call her our enablement queen. She has done an amazing job with building trust within our teams. She’s the one who does many of those one-to-one and one-to-few sessions. We did many virtual sessions before the launch, Zoom training where we would walk them through the tool, show them the benefits show them how we could customize things. And then we were very lucky with our professional services agreement.

We launched this in January right ahead of our revenue kickoff last year, and so we were able to have one of our Highspot reps actually come on site, and I think that was instrumental for us to be in person as a revenue group, and then have a Highspot person from the team there along with us as a leadership team and an enablement team all together in the room to be able to together walk through it, not just over Zoom.

I know that’s not something everyone can do and we were so lucky for it. But then post revenue kickoff, holding those consistent office hours and again, sharing best practices and just staying close with our team I think has been huge for us in getting people into the platform.

SS: You’ve mentioned a few times now during this conversation the importance of using data.

And we’ve seen in our customer base that having data is key to building trust and improving value. And I know that you are very much a data-driven enablement leader. How do you measure the impact of your enablement efforts and how do you leverage Highspot to help?

HG: Great question. Gone are the days of using our gut to make decisions and to determine what’s working and what’s not working. Although I’ve worked with many people who still feel comfortable in that way. For me, data is imperative. It tells us what’s working, and what’s not working, and it helps us craft a story.

And to quote, Real Housewives of Salt Lake City, right? I need proof, timeline, and screenshots. That’s really where I come in when I’m speaking with my teams and I’m speaking with leadership on what’s working or where we should make adjustments. And that’s with every tool that we have, especially in the economy that we’re in today, every dollar invested needs to have a return.

And if we’re not getting it, we need to figure out why. And a lot of that comes enablement team. So what are we doing to make sure that the teams are utilizing it properly? So for Highspot specifically, we report back monthly to marketing and to rev leadership. We have two separate meetings for marketing.

We report back on what content resonates the most with our clients. So not only what our reps are sending, but what’s really being viewed. If we have a PowerPoint presentation that has. 30 slides. Gosh, I hope no one’s sending one that’s that large. But if a client’s only looking at, three to five of them, those are the slides that we want to focus our attention on moving forward.

That’s what really resonates. And so for our marketing team, it’s been really helpful. Especially since we’ve just done this huge brand audit. And so we’ve really prioritized what pieces of collateral we’re going to adjust to the new brand outlines based on what’s been sent and what’s been engaged with.

But then for our rev leadership, we’re able to then see, we’re able to tie the analytics back with how conversations are actually progressing from prospecting to opportunities, closed won or closed lost. And I think that shows a lot of value back into the platform. And again, we’re able to do a lot more one-to-one, one to few, given how small of an organization we are.

We have about 60 sellers across our entire team. But telling that story with the data has been really helpful for us to show what’s working and then who we need to spend more time with to maximize their effectiveness as well.

SS: What are maybe also some of the key results you’ve achieved since switching to Highspot? Do you have any wins you can share?

HG: Our organization is a little different based on the technology that we sell. We offer a tool that helps individuals choose and use their benefits. And appreciate their benefits too. My marketing team would kill me if I didn’t throw that part in there. But we do, because of what we offer, we do 90% of all of our revenue right before the traditional open enrollment season.

So truly 90% of all of the deals that our sales team is going to sign are signed between August through October each year, which then leaves many months where we’re not closing deals. We can create opportunities, but we don’t know how fully they’re progressing. So we were really excited this year to actually have that full end-to-end deal cycle from prospecting to opportunities closed won.

We were able to pull some really awesome win stories in Q3 last year that we’re able to show what content was shared throughout the journey from prospecting before an opportunity was even created, and then from an opportunity being created to closed won, sometimes it’s a couple of weeks, a couple of months, but for a lot of time we’re doing prospecting, this time of year. So we’re looking for opportunities in February that are going to close and hopefully, August through October, and having that content to be able to show the journey has been able for us to streamline specifically with our master sales decks and our one-pagers and really when case studies are most relevant in being shared in the journey.

And so I think that’s helped us a lot with bringing that to the masses and scaling what content is best to share when and we’ve tagged it appropriately in Salesforce now. So it makes it really easy when your opportunity is progressing the content that’s being shown to you. So it’s taking the thinking out of it at this point and made it really easy. So they know exactly what to share and when.

SS: Heather, last question for you. What are some goals that you have for Jellyvision in the coming year and how do you plan to continue to evolve your enablement strategy to support key initiatives of the business? 

HG: Key initiatives are always changing. So we are going to continue to be nimble and pivot as needed.

But this year we’re super excited to lean into the recent updates that Highspot has had. We’ve been very AI-forward at Jellyvision. Our CEO has really leaned in and encouraged us to lean in. So, I’m excited about the new updates to the platform. We’re actually doing a relaunch next month to our teams to roll out what that looks like.

And then one of our major goals this year is to really maximize the usage of the digital sales rooms. Here we call them client microsites. That’s our internal language, but really maximizing what that looks like. That’s what it looks like for our reps to get more out of the platform as well.

SS: Heather, thank you so much for joining us. I really appreciate it. 

HG: Yeah. Thank you.

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