Episode 70: Innovating Enablement With Data and Technology

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 Sarah Gross. Thanks for joining us, Sarah. I’d love for you to tell us about yourself and your background. 

Sarah Gross: Shawnna, thank you so much for having me, I’m excited to be here today. I have spent a decade in sales and a decade in enablement, and absolutely love both spaces. I started my career as a BDR, moved into sales management and got the typical dashboard and quota, and very quickly realized there was a lot more to sales and to managing salespeople.

I ended up actually researching enablement and then got into being a practitioner myself. So, as I’ve built out teams over the years what’s been interesting is to watch how enablement went from L&D to how we think about making our team more productive, but we weren’t calling it productivity quite yet. We were like, “Oh, let’s get people from 100% to 110% of attainment” to now being the real drivers within the organization of how technology helps our team be more effective and therefore productive in what they’re doing day-to-day. 

SS: I love that and thank you again so much for joining us today. Now you and I have known each other for a while and I know that you focus deeply on a couple of core components when it comes to driving a business. That’s the people, processes, and technology. How does that approach guide the way that you build your enablement strategy? 

SG: Yeah, first things first, you have to have the right people in the right roles.

So I’m a big fan of, especially in a sales organization, right? Having that BDR, SDR structure, the account executive, the SE. And what’s important from an enablement lens is being able to make sure that everybody knows their role and function. It leads to the process side of things. So if everyone knows what role they’re playing in the sales process, then it is defining what that process is, right? Less of the upside of what are our sales stages and how we forecast, but more of what are the gates through which I need to uncover information from the customer and our internal selling team to advance, and to know that I’m in the right place of moving this opportunity forward and spending more time and resources on it.

How do we make sure that process then maps to the methodology that we’re using from a customer buying lens, as well as a selling buying lens? And then how do I make sure that we have the right technology, that I’m not asking my reps to copy and paste a Salesforce field into 15,000 different places, but rather Sales Navigator that’s layered with a Zoom info of the world and allows them to push information into that centralized repository in an easy way to build on account plans, to build on opportunity plans, and to have that structure of what good selling looks like. That’s the baseline, in my opinion, for what enablement has to have as the building blocks at the bottom of the house if you will. To then just start to do things like AI and getting into call recording and understanding what words are being used, when, where, and how.

And devising an enablement plan that is by cohorts of people that need a specific topical area. 

SS: I love that you established that baseline. What are some challenges that you’ve encountered as a leader when it comes to creating an effective enablement strategy, though? And how did you overcome those?

SG: The strategies have changed over the years. I’d say at the beginning of enablement, early 2010’s, right? It was a lot about what is it. Why is it different than L&D? Why would we invest in this different team and structure? Then we evolved into, okay, they, they run the LMS, right? They’re the people that give the training.

And they may have an action item coming out of it. And then we’ve gone into this world of, Okay, we have technologies that are supporting enablement now, which is fantastic. They’re designed for enablement, and they’re giving us the right level of analytics. But how do we, as practitioners, continue to stay that we’re elevating the value of our practice?

I still see where people are just trainers or they’re just go-to-market folks who get it out to the sales team. I hear that a lot. You’re the person who helps us communicate with the revenue team and speaks their language, which is a big win in and of itself, right? We’re not being called L and D anymore, but on the flip side of things, we’re not the seat at the table, driving the go-to-market strategy.

I do see that starting to change where more companies than ever are hiring VPs of enablement. They want to attach to the operational strategy and the go-to-market strategy and have a plan Where all three of those functions are working together there was this weird trend during COVID where everyone was down-leveling their enablement to save costs, and now I’m starting to see that flip again Where we’re hiring lots of folks that are at a senior level.

They want 10 plus, 15 plus years of enablement experience to guide them on “how do I drive that productivity lever?” “How do I be smarter in how we sell in the market?” Because we do have fewer salespeople and we have a bigger market that we have to attack.

SS: Now, as we talked about in that first question, people, process, and technology, on the people side, what are some of the key things you prioritize when you’re building a high-performing enablement team?

SG: I think the people side really matters in how you build out your enablement team so that you’re embedded enough to understand the business, right? For example, if you have a role that covers everything up to ISRs, right? Inside sales reps, where they’re both covering leads and running the sales process, you need a very different enabler to support that type of practice. And someone that’s maybe in an office with them, as an example, that’s where I think it makes sense when they’re all in the office. Or someone who has experience both in running a lead gen team, also a selling team, so that they can pull those together. 

As you think of the sales structure, that’s where I think enablement has to mirror. This is why enablement teams change from time to time because it’s normal that sales structures change,  and you have to make sure that we’re constantly evolving with them. When those two structures start to look different, like when I see enablement teams aligned by product, right? They’re seen as generalists and they’re less impactful to the overall business. 

SS: That makes sense. On the process side, how have you partnered with your key stakeholders to identify process gaps and solve those inefficiencies?

SG: That’s the question always. Having really strong ops partners and being part of the conversation that you have with your chief revenue officer is important.

I think that the way that works best is that ops gives you visibility to everything that they’re showing to the sales leader. If you have a different lens, the sales leader is looking at like, “Where do I have pockets of inefficiency that I could either reduce my head count or change that headcount around?”

You’re looking at it as, “How do I have cohorts people that maybe are at that 90% mark, that they would make a lot more money and we would make a lot more money if they were at 100% or 105%.” The way I look at the data that’s being provided to me is always, “How can I think of running cohorts of people?”

So for example, I’ve had in the past where I’ve got a discovery coach, someone that I can deploy if there are people in SDR land, AE land, and SC land that need that particular topic area. And by deploying them I’m keeping my business partners. So you’ve got that strategic person that they trust introducing the session with somebody that’s focused on that particular topical area to move the needle as it comes to productivity.

I’d expect that a lot of enablement teams are probably going to have someone who’s that AI specialist over time, where their entire job is to match that internal data set with what we are hearing from our enablement tools. And how can we deploy every call we’re looking at across the system?

Deploy, if we hear X word, one sheeter, a cheat sheet to the rep in the moment. It’s a talk track that gets deployed to our SDR organization, right? Maybe it’s even a technical validation asset that’s going to our enterprise reps as they run into X integration that they don’t run into all of the time.

So I’m starting to see where I almost think SEs are always a secret sauce to a lot of organizations. To me, it’s how we capture what’s in our SE’s minds and deploy it on every call that’s happening, not just the ones that an SE is attached to. 

SS: Absolutely. And then the last piece of the puzzle: technology. How does an enablement platform help you effectively bring your strategy to life? And in your opinion, what is the strategic value of a unified platform? 

SG: First and foremost that’s definitely evolved in the past, like five-ish years. Originally, I would say we were looking at just do you have SCORM packaging. It was very traditional instructional design technology that you needed.

Now, because we’re further away from what is traditional L&D, I’m seeing a lot of enablers really need their platform to drive, “What are we missing?” We’re running a discovery program, we’re running a negotiation program, and we’re running our new product launch. But what are people looking for in the system, whether that’s on the content side or the learning side that we’re not providing to them today? Or, what are we providing that nobody gives a shit about? And we’re wasting our time and resources? So, it’s an efficiency lever for enablers, which is what I see the platform as. The reason I think that content and learning have to be in the same place, is it’s part of the learner’s journey, right?

Humans either want to consume information in written format or video format for the most part, right? And as you take those two things, you have to meet the learner where they are. That’s something we all knew years ago. But now it’s not just meeting them where they are, it’s meeting them where they are at the right time.

And so it’s making it a self-service model that you can then look at analytics and drive what you’re putting out there to them in the most efficient way. So if you don’t have what content is someone consuming, what learning is someone consuming, and what are they sharing externally with their customers, you’re missing a piece of the puzzle.

Because they might be – another thing I’ve always been able to point out to my heads of revenue – is that we’re consuming and teaching this internally, but our customers are actually looking at this when we send it over to them. So there’s a disconnect between the two things that we really need to solve for.

SS: Now, obviously, if you make the investment in technology, you want to ensure that your reps are taking full advantage of it. What are some of your best practices for driving adoption of your enablement solution with your reps? 

SG: Ariel Lashaza, who’s someone who’s worked for me at a couple of organizations, did this extremely effectively. We brought it to the level of reps. Think of TikTok, we called it “What You Want to Know Wednesdays”. And it was a piece of information that they could try every single week. I think the way that these things work is it’s the curve, right?

That we always know. You got your earlier adopters, you got everybody in the middle, and then you have your late adopters. There are certain folks on every team, you know they’re not going to do it until we tell them they have to. Then there are people that you know are going to chomp at the bit to get anything. And then there are people in the middle that their manager has to tell them to do it. 

So I think it’s identifying who your early adopters are, especially as you do those fun, “What You Want to Know Wednesdays”. And let them drive the topics, because then they’re excited about it, they tell that middle crew, get them more excited about it, and ask them to go to shared and team meetings, and that’s how we’ve rolled things.

Having a little bit more structure around it, I think that it’s important that, one: it’s leadership-led. So you have a preview from the frontline manager level, up. What to be expected, how are we going to support you, what do we need from you? Very simply. Then as you actually roll things out to the team, it’s embedding that into your monthly learning.

However, you’re already communicating to the team and then it’s taking those early adopters, and showing them the impact on revenue, which is why I think that Highspot’s report of tracking opportunities related to Pitches is like money. Because you can go back and you can say, “Hey, you sent out 18 Pitches. Those were viewed 300 times, and you actually closed every single one of those deals. So, your rate of closure when you use the pitching functionality is 100%. What was your close rate before you did that? Maybe it’s 40%.” And so immediately to them, they see the ROI. I just think we have to, as enablers, always be selling. And the way that we sell is by using that data and analytics for our revenue team. 

SS: So on the topic of data I think that you have always been someone who has helped those around you succeed by really being inquisitive and leveraging that data, as you mentioned, to make business decisions. What are some of your best practices for, to the point you just made, measuring the business impact of enablement? 

SG: Best practice, one is, what’s your CRO measuring? if they’re being measured by ARR attainment and NRR, right? You have to know what those numbers are first and foremost. Secondly, it’s starting to break down, “Hey, CRO, if I did X, do you think that would move the needle on what you’re being measured against?”

If that’s the case, let’s put this in place, and let’s put a stop in the sand where we are today and measure it again in 6 months. So I think that alignment up front is really important and making sure you’re not just tracking to time-to-ramp if they don’t care about it, right? Super important you’re aligned.

Thing two is buddying up with the ops team and saying, “I know you’re measuring this. I want to measure how we can impact this as a team. You’re probably making some operational changes. Maybe it’s quota, maybe it’s territory alignment, et cetera. Let me build off of that. I’ll actually help you communicate that to the reps that it’s happening to. And, once we communicate that, instead of it being a 10-minute call, let’s make it a 30-minute call. Where on the last twenty minutes, let’s talk about how they can attain that number in a better and more succinct way. And maybe what Sales Plays are we running to support them in hitting those new targets that we’ve provided?”

So it shows us the unity between ops and enablement, which is such an important part. And then it’s coming back. I’ve always said, at a minimum, quarterly reviews. What was the enablement impact? And that’s where I do think we should push our vendors to support us in that, right? They should be providing us with Scorecards.

They should be providing us insight into what’s going on in our system from their CSMs. And I encourage all of my enablement peers to be requesting that. It is well within our rights to push that we need that level of data to run our businesses. Think of a CMO or CRO. They’ve been holding vendors accountable for providing them that since the beginning of time.

And it’s now our time to do that so that we can have those executive-level conversations. And we’re not just being like, “Oh, we launched the learning path.” Or, “We launched the huddle.” That’s fantastic, but we’ve all moved past that. It’s not about you putting it out there. It’s about, did it hit the mark actively, proactively sharing what did or did not, and what you’re going to do next.

SS: To that executive leader point, given kind of your wealth of experience and enablement, how have you gained buy-in and support for your enablement strategy with your executive leaders? 

SG: It’s always the fun thing that when you get a new CRO or a new C-level, right? How do you set their expectations of enablement, right? Honestly, there’s still a lot of different definitions out there of what a good enablement team looks like. I think it’s really important that up front you understand: what are their priorities and how are they being measured? I didn’t say, what are they measuring? How are they being measured? 

Every CRO has something that the board is asking them for. That’s just part of the game, and part of being in sales. And it’s usually different than what quota is being assigned out to their team, et cetera. I think the second piece of that is then saying, “How can I communicate this with you? What frequency would you like to see updates from me and in what format?” If they don’t have a proposed format, something I learned from an early CRO of mine is CAB: Conviction, Action, Benefit. Having three columns on the screen: what are we convicted to do together this quarter? Again, that’s a together statement.

What actions am I taking, right? Or do I need you to take to support that? And I always suggest there’s a two-way street there. And then what’s the benefit? What is the thing that we are measuring? And if we come back and it happens, we know that we are successful in this. Super simple, but I would go on whatever format your particular leader is looking for.

They might have a different version of that. Or propose, hey, if I did this, would that work for you? I don’t think it should ever be more than one page. It shouldn’t be a ton of charts and a ton of things. Solely because that’s your job as enablement. Our job to them is that we’re measuring those big projects together.

SS: I love that advice and that acronym. Last question for you, Sarah, where do you see the future of enablement going over the next few years? And what are you most excited about? 

SG: That’s a good one. We’ve come a long way in a very short amount of time as a profession. I definitely think that AI is a big part of our future. It’s a big part of everybody’s. It’s a big part of humans. I think as enablers the thing we do that is so critical to every business is we understand how humans work, think, and do. So it’s using AI to be more human and to help our team with those productivity levers.

So think of right now we run a pitch contest and you use your top three reps, you have them pre-recorded as an example and then you launch it to everybody and you have a grading criteria in the system. Maybe you have something like a Copilot of one of these SORMs that’s running and giving a little bit of insight. But, in the future, think about if that could simulate a customer in their territory, in their patch that they’re trying to sell to today. It could be somebody that looks and feels like their particular segment. That becomes even more impactful as we continue to grow. And I do see that’s where we’re going.

I want to level set to all CROs out there, that’s not where our technology is today. But, it is absolutely something that’s within reach in the next couple of months. I also see a lot more happening around the traditional Salesforce where we used to serve up, “Hey, have you thought about sending this white paper type of thing?” Integrated more into the call intelligence world where you’re in a call, and it says, “Hey, you just hit a roadblock right in that conversation. Consider this objection handling technique,” or, “Consider saying you want to bring your SE in to do this technical validation based on the integration they just asked for.”

There’s a lot more of that to come as we continue down the path. What am I most excited about? It is AI. I say that with a little hesitancy in my voice. I think that it’s a way for enablement to scale without having to have humans and to be able to spend time doing the things that we love doing, which is talking to reps gathering feedback, and being part of the collaboration. That is revenue.

I think we spend a lot of time right now in some cases behind the scenes in our LMS and CMS because they’re not totally optimized. So if we are in this AI lens where our CMS is sending us an email every morning of what’s good, bad, and not happening in the system, and we’re not going through hundreds of thousands of pieces of data, that gives you so much more time to be in front of the team and with the team.

Right now, I see enablers having to choose one or the other that they’re really good at. And the people who are behind the scenes sometimes aren’t part of the executive meetings because they don’t have enough face time, but they’re really good at the right programs, et cetera, to get out.

And then some people who have too much face time, and not enough behind the scenes are dinged that they’re not analytical enough, or they’re not using AI to drive their business. So it’s a push-pull today. I think that our vendors are really catching up with supporting enablement. Just like Salesforce has always supported a revenue organization in design that will get us to where we need to go in the future. So, I am excited about AI and because I think it will give us more time to be the human elements in front of our revenue organization. 

SS: I love that. And I know we are very excited about Highspot Copilot as well here and all the AI innovation we have coming. And we’re going to actually be announcing some of that at our Spring Launch Discover Webcast shortly. So thank you, Sarah, so much for taking the time to chat with us. I really appreciate it. 

SG: Absolutely. It was my pleasure. 

SS: To our audience, thank you 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.