Raising Your Sales Enablement Game

Jessica Ly: I'm here with Kyle Abel, who is the sales enablement leader at Guidewire. Welcome to the show, Kyle.

Kyle Abel: Thanks, Jessica. It's an honor to be here.

Jessica Ly: I know about Guidewire a little bit. You guys provide technology for the insurance companies having the tools that they can then allow their consumers to go in and make changes, and also just managing the relationship with partners and all that. It's been you guys have been doing really well been growing really well. And I wanted to hear more about the innovation taking place and then go into sales enablement because I know you have a lot of tips to share with us. How has it been going?

Kyle Abel: Yeah, it's been, it's been amazing. I started in the industry in the mid-aughts. So 2005 2006, and until about, I want to say 2010 2011, it was kind of slow, as far as innovation and the iPhone effects definitely took in too cold. And all of the customer expectations or consumer expectations of all of us of just expecting personalized experience and instant information on your phone. And you know, Amazon with predicting what you might be interested in. All of those expectations hit a lot of different industries, as I'm sure you know, and property and casualty insurance are absolutely one of those. I'd be hard-pressed to find anyone at this point that would not like a very easy one-click, you know, experienced buying insurance. So it's been pretty exciting the last 10 years, I would say in property and casualty, just trying to meet those consumer demands. And a lot of old systems running 30-year-old codes that just weren't built with those kinds of demands on them. So it's been great. And we've been really fortunate to have over 400 customers now worldwide, and we are just honored to serve them.

Jessica Ly: Yeah, I know. You also have shifted your product from the traditional on-prem kind to now completely cloud technology. You have to rewrite all of that. So it's been a big change for you to take advantage of the cloud transformation here. Your clients are very big clients. So these are multi-million dollar deals. He’s a long sales cycle. You have over 225 sellers that you're supporting on the sales enablement front. So let's talk about that. You know, one of the challenges sales enablement has is being able to look at how your effort, your content, your training programs, and all of that truly make a difference. But tell us about that. How do you measure? What are some of the KPIs?

Kyle Abel: Sure, so we follow a Patrick model loosely, and this is something we've gotten better at. I’ve been at Guidewire in sales enablement for eight years. And every year, we try to get a little bit better. But it all starts we have a consistent survey we do at the end of any workshop or session that we do. And it's just as simple. How useful was this very useful to not useful. And so that gives us some instant feedback. And we've used that scale. We converted from zero to 100. So it has a little more context. But we use that for. I think the entire eight years that I've been there. So that gives us some level to compare our programs from one to another. Another thing we do is is an impact score. So this gets a little farther from just was it useful to how useful was it? So we may ask a question relevant to the content before the session or at the beginning of the session? Like how confident are you doing X selling X, Y, and Z? Or if A, B and C happened? How would you respond and have some multiple choice? And then we'll do the session? And then we'll ask the exact same question at the end. And that meant that it allowed us to measure the actual impact. Where are we moving the needle? By what percent, right? And then some of the other things that we've started incorporating over the last couple of years is quizzes, so having active recall of the training, so sometimes we'll do it as it's happening, because we feel like that may be needed for certain aspects. But increasingly, we are trying to provide a little bit of space a week, two weeks before we have that quiz. So again, it kind of keeps it somewhat top of mind, right if you tried to extend out that timeframe a little bit to keep it top of mind. And then one of the things we're trying to do really the last year or two is after a period of time, call it three months after a training event. We may go back to the attendees and say, okay, it's been three months. Have you used this out in the field? If so, What has been the feedback? If not, Why? What else would have been helpful during the training, right? So you're getting a little further away from the actual event or the training or the coaching or whatever, whatever the enablement is. And then the last piece, which is the hardest, but I think ultimately is going to be the piece that allows you to complete the whole view of an enablement event, is tying attendance and participation in a training event to actual revenue influencing revenue. So we're starting to get some tools in place that makes us a little bit easier where we can say, let me see all of the people that attended this workshop and their percentage of quota attainment, and can we correlate, there won't be, it's impossible to make causation of it. But can we correlate an attendance of this training with higher quota attainment, for example? So there's not any one of those is more important than the other. There’s no silver bullet. Unfortunately, enablement, believe me, we've been looking for eight years. But if you take all of that together, you can paint a pretty good picture of how effective your enablement sessions are.

Jessica Ly: Yeah, I think that with the use of digital content and digital assets, you can see the conversion of a prospect looking at certain content you're sharing to whether they then get more engaged in this interaction as they're moving down that pipeline to actually take on a conversation, getting a demo signing up for PLC and all that, and I think so, you know, I think that the analytics are there, and the data will allow you to track it more accurately as you use more digital assets.

Kyle Abel: Yeah. And what we're finding is a lot of the tools now will not only show you, customer XYZ accessed this presentation or this video, it will show you how much time they spent on a particular slide or a page if it's a PDF or, you know, did they watch the entire video, or did they drop off after two minutes or something? So those deeper analytics give you great insight into what they're most interested in, obviously, and you can tailor the rest of your touchpoints with the customer that way, some of the systems that we're looking at will, based on the attributes of the deal of the product type, or the geography or something like that stage of the deal, it will actually suggest training to the seller, or other relevant content. So we're super excited about just the possibilities that really didn't exist five years ago. So it's pretty exciting.

Jessica Ly: The one thing that I find fascinating is how much personalize specific deal content you in the enablement team is actually helping the sales reps to close deals, because often you're creating content as well to be scalable for a lot of people, right. But here, you're talking about a specific company you're targeting and the content you need to help close that deal.

Kyle Abel: Yeah, and I give credit to the team members and the leaders that started sales enablement at Guidewire, that they always impressed upon us the need to carve out some time, in our week or month, even just buffer in case something comes up that we can help out in a deal. And we've always done that. We found it's incredibly helpful for us to just continue the relationship with the sellers. And so when we are rolling out the scalable programs that they're buying in, and we can get the feedback and so forth, but it really helps us keep connected to the field and what the customers are actually asking for. And what the sellers think is most useful out in the field. So it's, I think of it as kind of a virtuous cycle that we learn about what they want on the deal. Specifically, we help them create that and then we can back it up and say, okay, now how can we scale this knowledge or scale this practice to the rest of the world? So yeah, it's something we've always done. And I highly recommend that further enablement teams.

Jessica Ly: And you have all in-house talent, right for actually strategizing and creating the content you're so in a way, it's like, I feel your team must be very thrilled to actually have the responsibility and also given a chance to make creative assets.

Kyle Abel: Yeah, I think so. It's a bit of credibility building that you have to do. It's interesting when you see someone new come on the team. You can almost chart the point in their tenure when they start being pulled into deals. There's some credibility building that you have to do just because a sales rep Or any seller is going to be hesitant to bring in someone that they don't really know, to really work on deals that they're working on assets are going to send out. So it's a good kind of test, a little litmus test of how you're doing how you're being perceived. But yeah, it's a chance to try new things to put into practice all the things that we actually teach. So to put our money where our mouth is, so to speak, and, and show that what we teach, we actually believe in and that we, we can execute.

Jessica Ly: Now there are a couple of best practices that I'd like to ask you to share. Cuz you've been doing it for a while, and certain things you have found to be highly recommended, right? Tell us about the consistent programs? And what else do you want to share?

Kyle Abel: Sure. So I make it my own personal mission at Guidewire to really protect the sellers’ time and attention. Because by definition, when you ask them to consume training of any kind, you're asking them to not spend time selling, and instead to focus your time on the training. So we're very deliberate and putting ourselves in the seller’s shoes, and what would they expect? What would make their lives easiest, and we've come to the conclusion that as far as training goes, internal focus training, consistency, and the where to find training when do they expect the training, what that training should look like. That consistency is really important because you don't want the sellers guessing. Where do I go to find this training versus this other training, right that I just time that they don't need to spend, if you can avoid it, right, it should be a single spot? And they should know, every Friday, we have a webinar or every month, we have a newsletter, that's going to come. And those are two things that, specifically that we have done for eight years, we actually don't do a weekly webinar. It’s usually every other week. Sometimes it is weekly, depending on if we have a product launch or something like that. But it's the same time, Friday 10 am in Dallas time, which is where I am, it's 45 minutes long, it has a very familiar flow to it, we know there's going to be questions at the end, we know the following Monday, you're going to get a recording if you didn't see it, right. So all that consistency, I think, is very important. And then on the monthly newsletter, we just recognize that if a seller has an active deal, they are going to head down, they're not they're really not going to be looking out for training this coming or new assets. So we put into place a monthly newsletter that just spans the previous month. And it's kind of in case you missed it. So will bubble up the training, the new assets, the new customer stories, or when stories write anything that they if they were heads down on a deal that they should know about, we'll put it in that newsletter and it comes to the second Thursday of every month at the same time in the same format, which we've tweaked the format a little bit here and there. But by and large, it's the same. So we really feel strongly that consistency is predictability are really important.

Jessica Ly: Yes, I agree with you. You don't want them to be wasting their time looking for an asset or training that they miss. So yes, absolutely. These are great tips. Okay, Kyle, the years ending. It's been a challenging year, but there must be some changes that you probably think it's good to keep next year, even once we're allowed to get back together. Right? Tell us when you're thinking.

Kyle Abel: Yeah, I would suggest that every team take the opportunity to do a year-long retrospect, not a year-long, but a retrospective over the past year. We'll be doing this, and my team will be doing this when we get together here in a couple of weeks. But everyone is rightfully so ready to turn the page on 2020. But I think it would be a missed opportunity not to take a look back and see what some of the things that we had to do that maybe we would like to keep doing were. So, for example, for us, one of the things that we're looking at doing is we were forced to do a virtual sales kickoff. Our fiscal year ends at the end of July. So in August, we've normally brought everyone together, all 200 plus sellers, very time-consuming, obviously very expensive. And we did that virtually, Of course, and we actually got a lot of positive feedback and a lot of efficiencies that we gained not only in the preparation, but having speakers read it more readily available and then people obviously not having to travel from different parts of the world. So we're looking at, we've normally had two of those, we're looking at doing one probably at the beginning of the year because it's more of a celebration, a kickoff kind of feels. So having everyone together makes sense. But maybe the mid-year one, doing that virtually. So again, we can not have to have everyone travel, you know, both times for just a couple of days. So that's one of the things we're doing, as well as just some of the lessons learned about facilitating workshops, virtually it's just different, right? Having not trying to do this, a meeting the exact same way that you would do. Suppose you're all in the same room and trying to do that. Over zoom, that doesn't work. So we've actually learned a lot about that. But yeah, that'd be my suggestion. And what we're looking forward to is pulling out the things that we were forced to do that actually might be good things to keep doing, and just try to get some kind of positive out of this terrible COVID experience.

Jessica Ly: Great idea. I think we're gonna be doing that too. Because, you know, working remotely and being able to reach out to so many speakers outside of Silicon Valley has been a big plus. So that's also an example or on my side where I think we're going to be keeping on doing that.

Kyle Abel: Yep, I think for the sellers, I don't know how readily the customers will be opening their doors for people just getting off the plane and so forth. There might be a long tail on that or maybe an indefinite that the access you have the in-person access is probably going to be a little more limited. So just taking another look at what are the activities and deal cycle that really must be done in person or should be done in person and what things might actually be better. Virtually, I think, going through that analysis, we're going to be doing that a lot this year and making recommendations along with the sales managers.

Jessica Ly: That's right, the best of both worlds, right. Thank you for being on the show, Kyle. It’s been a pleasure talking with you.

Kyle Abel: Thank you, Jessica.