Episode 233: Kelley Jarrett on Taking a Data-Driven Approach to Enablement

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs.

Today I’m excited to have Kelley Jarrett from Gainsight join us. Kelley, I would love for you to introduce yourself, your role, and your organization to our audience.

Kelley Jarrett: Hi Shawnna, it’s nice to be here. My name is Kelley Jarrett. I head up kind of a three-part team here at Gainsight. It’s sales strategy, enablement, and operations. I have been with Gainsight for just under two years now and was actually brought in to build the enablement function here at Gainsight. We had one individual who was leading that effort and as Gainsight was heading into a growth period and fast growth and scale it was important to the company to bring in a leader to build this team so that we could help the sales organization at Gainsight really scale our sales function. I’ve been with Gainsight for just under two years. If you’re not familiar with what Gainsight does, essentially we help companies build deep and lasting relationships with their customers through customer success and product adoption and community solution platform. It’s been a great couple of years.

SS: We’re really excited to have you here Kelley. As you said in your intro, you recently added sales ops to your team. Can you share how this has changed the way that you think about enablement as a function within Gainsight?

KJ: It really has been an interesting evolution of this function since I joined. A lot of people think of enablement as enabling or training sellers on what they need to know to sell but I think of it a little bit differently. I think our job is to ensure that all of our team’s time, energy, effort, and resources really go to four key objectives. One is to give sellers the tools, skills, and knowledge they need. Two is to sell more to increase selling time. Three is to keep them happy and engaged in the territory and then finally to future-proof the sales organization for consistency and scale the last one is really important to be able to leverage metrics and data in order to find the right areas of focus for the sales team.

SS: What are some of the key points of intersection between enablement and sales ops? How would you say the two complement each other and how can they best collaborate for shared success?

KJ: Yeah, it’s a great question because I know not all enablement functions really have these two teams aligned super closely. I truly believe that when these groups are aligned it is a game changer for Gainsight and could be a game changer for other companies. It really kind of completes the full circle in my opinion. You have a strategy that is really all about sales methodology and sales processes and combining that with the data and tools component, which is, you know, everything from account scoring to run-of-business data tracking, to optimizing the tech stack. Then finally sort of the last piece of this circle is enablement and that’s getting the right message at the right time to the field.

I feel like these three components really can function together so that we can ensure that our time and resources are ruthless, and prioritized and make sure that we are getting the right message to the right sellers that are also going to move the needle for the key business objectives for the company. It’s important to kind of have all of those working together and in tandem on common objectives and goals. If they’re separate, it makes it a little bit harder to ensure that we are all working towards the same objectives and the same goals. There are a couple of key points of intersection. I can give a couple of examples if it would be useful to kind of explain how we leverage the operations group alongside the enablement team.

SS: Yes, I’d love for you to dig more into that.

KJ: One of those is we can look at our operations group and ask for some metrics that we know are meaningful to our business. We, of course, are part of the vista family at Gainsight and there are some core metrics that we need to track and watch to make sure that we are not only performing in accordance with what they hope and expect from our company but also to ensure that we’re set up for the future of what Gainsight really needs to grow into. One example of this is, you know, we run a prospecting program within our enablement team. Essentially that prospecting program allows us to focus on what’s important to be prospecting into at any certain time within the business. In Q3, SAAS companies everywhere started to see a slowdown in buyers. We started to see that deal progression was a little bit slower than normal and that was in large part due to uncertainty and fear in the market. With the prospecting program that we had, we knew that cold outreach might not be the best place to start, so we shifted our enablement focus using the data that was telling us that we were starting to see a slowdown and deals and opportunities and we shift that program to focus on deal progression rather than cold outreach to new prospects.

What that did for us that we saw in the data was that it actually ended up giving us a better mix of late-stage opportunities heading into Q4 than we thought was going to be there. It was pretty exciting for us to be able to take a look at the data, see some things that were happening within the business and then use our great enablement engine to really get after the areas of greatest need for the company and help those buyers overcome some of those market fears that they were seeing.

SS: I love the synergy there. You touched on it a little bit but I’d love it if you could drill in a little further. How do you then take that data-driven approach to your enablement strategy?

KJ: There are a lot of ways that you can incorporate data into an enablement strategy and it always comes back to me to where do we need to focus right now? Different sales teams have different needs at any given time and so your resources can really be strapped. What we’ve learned to do is leverage the data to understand where there are common needs across all of the sales teams and that really allows us to use our resources most effectively where we can move the needle most. So that’s super important. One of the other collaborations, in addition to simple data, is how we’ve incorporated optimizing tools. I know this is something that a lot of enablement teams struggle with how do we make sure that our sales team is leveraging tools most effectively? Now that we have that operations group within our team, we’re able to leverage these tools more effectively.

For example, we use the sales methodology that incorporates MEDDIC, and what we’ve done in our conversation analytics tool is we’ve set up trackers so that we can see when the MEDDIC concepts are being used in conversations and how that affects the progression of those deals and even the win rates for those teams. Even just a little tweak like that, using some of the technology a little more effectively that we weren’t necessarily doing prior to having these teams together has really allowed us to see where there are some opportunities for improvement and give real examples to sales and how they can just do a better job and what they’re already doing well.

SS: I think that’s fantastic. For sales enablement teams that may be less first in leveraging data, what advice do you have for them to embrace a data-driven mindset, and what is the importance of having that type of mindset?

KJ: I think with data you can make the data basically say what you wanted to say at any given time, which is a common mistake and or a common issue that a lot of operations teams face. For those that are new to leveraging data in the enablement team, I would suggest starting small. There’s so much out there, don’t try to do too much at the outset. Start with the basics and there’s an acronym that we use at Gainsight to really try to get tight on what we’re trying to accomplish from a data perspective that allows us to orient our programs according to where the areas of greatest needs are. That acronym is AIR: activities, indicators, and results. The way we look at it and if you’re just getting started with leveraging data and your enablement programs, one way you can look at it is what are the key activities or behaviors that you need your sellers to perform to ensure you hit your goals.

For us, these are things like outbound activities and meetings. Like I said before, we are doing some conversation tracking to make sure the behaviors are there, but that’s a little more advanced. You can simply look at the number of emails or outbound calls as an example. For indicators, indicators are typically pieces of data that are indicating whether or not you’re going to hit your results, so the pipeline is a great one. If you’re new to checking data to enable your efforts, you can look at pipeline coverage and pipeline products and that will help you understand if you’re on the right track for hitting your numbers. Then, of course, results can be as simple as bookings, but it can also incorporate other results that you should track, like win rate, average sales price, and those types of metrics. One key kind of underlying principle that we follow within this AIR concept is we track trending data which actually gives us a better understanding, not necessarily of actuals because sometimes those are less meaningful, but rather what’s happening over time and is your sales organization as a whole and teams getting better or getting worse or staying the same. If you can sort of keep the AIR concept in mind and look at it from a trend perspective, it will give you a pretty good understanding of where your sales enablement team needs to focus their efforts to build skills and knowledge within your team.

SS: Fantastic. To drill into this a little bit more, what are some of the core metrics that you and your team track to measure enablement impact?

KJ: For us, we typically use the AIR concept as well, but we’re just taking it a little bit further than what I mentioned before with getting started with AIR. We’re looking at emails, calls, and the percentage of our sales team that is driving the pipeline for different products that we think should be in a higher growth category for our company. We’re just keeping an eye on slightly more detailed metrics that follow the same AIR concepts that I mentioned before.

SS: That’s phenomenal. The last question for you is, how does this data help you better influence business priorities?

KJ: It comes full circle to why we brought these teams together in the first place, which was we’re all SaaS professionals trying to be better at ruthless prioritization, especially in today’s economy. We have to do more with the same amount of people and we really need to focus our efforts on what are those critical skills and critical knowledge that our sales team needs to know and needs to have in order to optimize their days and data really help us ruthless prioritize. It helps us to give sales managers access and an understanding of where they’re spending their time and where they may need to shift their priorities to ensure they’re supporting their teammates in the way that’s going to get the best results and support them in a way that they need to be supported in today’s environment. It also puts information in the hands of sellers who really want to own their territory. We have a really great sales team at Gainsight. They care about their customers, they care about what we do for our customers, and at the end of the day, while they’re in sales and they want to sell, they also want to help customers become successful. Our job as an operations team is really to give them the right resources and the right understanding of their own personal data so that they know that not only are they hitting their metrics to sell but that we’re also providing them with an understanding of how that will impact the results of the customers that they’re serving, which is a huge part of why I think we’re different here at Gainsight.

We have a methodology at Gainsight called the human-first selling methodology and the difference between a typical sales process that is very inward-focused and a checklist focused by the sellers, we are really oriented around the needs of the buyer and the way that we can help be the front line to that that change in the market is by providing our sellers with the right information they need to know if their job is actually moving the needle for their customer’s success. We talked a lot about some of the selling resources that we have and some of the data that we use in our day-to-day operations, but at the end of the day, it’s all about business outcomes for our customers. We expose those to our sellers, we provide access to information that helps them understand what their work is and what their job is actually doing for the customers that they’re serving. At the end of the day, when we think about our business priorities, it is to serve that market more effectively. We want our sellers to sing from that same sheet of music as well.

SS: Fantastic. I loved this conversation, Kelley. Thank you so much for joining us today.

KJ: No problem. It was a pleasure, Shawnna.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there is something you’d like to share or a topic you’d like to learn more about, please let us know we’d love to hear from you.

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