Evolution of Sales Enablement

Jessica Ly: I'm here with Glenn Clark, who is the director of sales enablement at Smartsheet. Hi, Glen.

Glenn Clark: Hi there.

Jessica Ly: I'm so glad you're here to talk about sales enablement because I think that Smartsheet is a hugely successful company. And you've got a large team supporting 400 sales reps. These are direct sales reps. So wanted to get your thoughts on the evolution of sales enablement and the journey and make some of the best practices that you'd like to share. But first, let's just say a little bit about what does Smartsheet do? I noticed the enterprise platform but tell us a little bit about the use case.

Glenn Clark: Sure. Absolutely. So Smartsheet is a platform that empowers everyone to improve how they work. And what do I mean by that? Today, a lot of businesses struggle with this problem of unstructured work, and what Smartsheet can do on any level, whether it's the enterprise level, it's on the leadership level, or it's on the user level, can help those individuals navigate that unstructured work problem that they have to go ahead and add more structure and then ultimately get more execution done.

Jessica Ly: And you've got what 75% of the Fortune 500 companies using, right?

Glenn Clark: Yes, I think it is a little higher than that now, but yes, we do.

Jessica Ly: That's great. Let's hear about sales enablement. You know, I mean, 400 people to empower and help them to be successful. What have you done? That's work well?

Glenn Clark: Sure. So the first thing that when you think about 400 and 400 may be a large number to some and a very small number to others. But as I think about what it meant to me, when I first started at Smartsheet, there were 35 salespeople. And so now there's 400. And so along the way, the biggest thing that I've had to incorporate is how do I scale? Because as most of the fellow sales enablement folks out there know, oftentimes, we don't have the opportunity to scale at the same pace as the field does or the sales team. And so we have to think about scale in all we do. And to me, that's one of the fun things about my role is I get to solve problems in a way that is doing things more with less and in a scalable way. And I think as we continue to grow, part of what will help continue the success we have here is just that, that continued perception of or continued focus on, how do we ensure that any efforts that we embark on are addressing the larger audience because it there's no way for us to do it in a one on one basis.

Jessica Ly: Okay. Now, I think that a lot of companies face the challenge of having silos. You know, someone needs this content for one particular audience. Someone else creates a different content. And over time, there's just so much content, and it's hard for the sales rep to know which content to use just spending time searching is an issue. You already addressed that.

Glenn Clark: So that's a good question. The main thing that we try and do is we try to number one, let the business know the role of enablement because in some cases, those silos are created because the business is not aware of the value that enablement can bring. The other thing that we do is we do offer some moderation of the content and so being able to kind of be the funnel, that content goes through that, then the enablement team is able to kind of get out to the field is a huge benefit to the field. And I want to talk a moment about kind of what that means, in terms of how sales enablement does that, number one. Sales enablement should, if they have not already done so, create a relationship where the field feels as though they are a trusted partner. Those things that come from sales enablement camp have been vetted, it's trusted, it's relevant, and how do you gain that relationship? It's through the experience and the expertise that sales enablement offers many sales enablement folks have been salespeople before. And so they understand the world of a salesperson, but they also understand the world of enabling salespeople as well. And that long time ago Dark Ages, it used to be that sales enablement was sales training and in those times, you had to be the subject matter expert. So if you were going to train someone on a sales skill, you had to be the expert who has experienced doing that and then design and deliver that content. But today, there's so much great content out there. There are a lot of experts out there. Some that are don't want to be in sales enablement but have a point of view on how to be an effective salesperson. So I believe that the role of sales enablement has adjusted to being one of yes, we have some expertise. But we also have the ability to curate content. And what I mean by that is, we, through our experience, through our understanding of our business, and through knowing what great information is out there, we can kind of create this convergence, that when we surface this information to salespeople, and you've got that relationship of trust, we're actually helping salespeople catch a pass in stride with regards to valuable information. Without that, salespeople who want to learn more or want to leverage best practices might be out there looking for things that they can incorporate into their tool bag. And the challenge with that is that it can be wasted cycles. It's the wild west out there with lots of information around how to prospect and how to manage your territory and manage your accounts. And if a salesperson doesn't have a trusted source out there, then they can spend a lot of time looking for that. Whereas sales enablement can actually help filter that and translate and add a wrapper on that content so that the reps feel as though it's valuable because it came from a trusted internal resource.

Jessica Ly: Right? So more selling, less researching for content.

Glenn Clark: Of course, I don't know any salespeople that would have a problem with the opportunity to sell more and not spend as much time researching.

Jessica Ly: I want to ask about your actual blended training partner. It sounds like it's a pretty thorough and long process of training. And then there's ongoing afterward.

Glenn Clark: Oh, yes. Well, you know, when I think about enablement, I don't think it's a moment in time effort. I think it's when you own enablement. You own the development and the success of salespeople for their entire tenure at the company. It's a joint effort. So I don't want to pretend that it's only a sales enablement job. But one area where sales enablement gets to be involved early is definitely during the onboarding piece. And so my program, one of the things that I try to practice as a sales enablement professional is the experience that salespeople go through. Because more and more that's important, it can actually color and create the tone for what the first six months or nine months of our sales reps’ tenure as a company. And so, from my vantage point, part of our ability to set the tone and generate excitement has been the way in which we've structured our onboarding. So when we have folks that go through our onboarding, we're fortunate in that we have enablement in our various sales offices that actually onboard folks within the sales office. So now you have an audience that is with you for at least 30 days when and if they're an inside sales team, and longer. And what we do with that time is we actually blend it so that it's not your traditional boot camp style eight hours a day in a classroom for two weeks. We actually take that classroom time have spread it out over an entire month. So in between, you have opportunities to shadow to meet with folks you're going to be working with, work on, do workshops, get certified, do self-paced learning, save all of those opportunities, and it's mixed in. And the reason why we find that valuable is it a lot of times, what happens if you have just straight boot camp is fatigue sets in later on in the boot camp. Because the reps know it's eight hours of being in the classroom, and they're kind of getting tired. Whereas they were, we're adjusting how you take in your information. So you never really kind of settle into a pattern, which is exciting. The other thing that we do with the onboarding is we actually time the content to when they'll need it. So when you do boot camp style trainings, you have a certain amount of time, so you've got a lot of information that you have to cover within that set amount of time. Whereas for us, because we've got an audience for 30 days, we'll hold off on doing things like Salesforce training until you actually get your leads turned on. Or we'll hold off on getting into the deeper aspects of our product until you have a chance to understand and get your hands dirty on the basics. But the other thing to your point around the length, once you're done with the first 30 days, we don't consider you're done with onboarding. We actually consider onboarding to be the first 180 days and that's not brand new information. It’s probably won't be a surprise to most. What we do though that might be a little bit different is once you exit onboarding, we actually have a dedicated coach on our team, that person's single role is to focus on ensuring rep, productivity throughout their ramp, not just hitting that, but exceeding that now, and that can be in any number of ways whether you exceed your ramp in a shorter timeframe or you exceed your ramp by more than what is anticipated. But the other thing that's equally important is now that you've maybe you've crushed your ramp, which is amazing. Now, what do you do? We, that coach's job for the next five months is to make sure that you're strengthening your ability to get as close to if not exceed your attainment on a regular basis so that when they exit their first 180 days, the managers who get those reps feel very confident that rep is on a path to hit club their first year. And so the reason we did that was that we noticed and the researchers out there that in a lot of cases, once it gets real ramp is done, reps can fall off a cliff. And trying to recover from that fall-off is really difficult. And so what we did is we want to get ahead of that clip, we want to provide a safety net so so that coaches working with them for five months. And then, once they're done with their first 180 days, they transition to what we would call our ongoing phase. And that's where I'm able to managers are doing Ad Hoc trainings, they're doing coaching spot coaching, they're doing new skills or new product training that comes out that on an ongoing basis. And it's working well for us. We still have lots of opportunities in front of us. And I would say until you everybody in the company is hitting 100% attainment, we've got a lot of opportunities, but it is working. And the feedback that we get from the folks that go through it is really positive.

Jessica Ly: That's wonderful. And I'm impressed that you have this dedicated coaching service for five months. I mean, that's unheard of, actually. I’ve not heard any sales enablement team talk about that kind of dedication for that long.

Glenn Clark: Well, we landed on that for a couple of different reasons. Number one, prior to that role, folks were nominated as mentors on the respective team. So if I'm a manager, I've got eight people I got a new headcount, I'm gonna nominate a mentor on my team to work with that new hire for X amount of months to try and get that person up to speed. And that's great because you have that one-on-one connection for an extended period of time, but that mentor is also trying to close business and hit their number. And you're also, in a lot of cases, only getting that mentor’s perspective on how to be a successful salesperson. And so what the learning coach does on my team, is there a direct line into our larger enablement efforts, and so they can kind of help champion that as they're approaching. But second of all, that person is not a quota-carrying person. So they can spend all of their time working with reps at scale and one on one as needed, driving a consistent message that is born through enablement and sales, leadership alignment. And you get to do that at scale. So now you have an army of salespeople that have the same information, the same technique, and I think it is. It’s the way to go. I think that what really has helped this role gain traction here at Smartsheet is the fact that it actually helps reps exceed their ramp. So it helps managers get unrecognized revenue. It’s not revenue they anticipated. And that's meaningful to sales leadership. The other thing that this does, and this is kind of a topic for another day, is on the coaching side of things, this person is coaching, they're not managing these folks, they're coaching them so that if this learning coach has aspirations of becoming a sales leader, they will have already checked the box on being able to be an effective coach, which a lot of times salespeople that are promoted because they are amazing salespeople haven't had a lot of time to coach and so they're trying to replicate amongst their team themselves without the skill set around being a good coach, whereas now you anybody in this role has had months of being able to coach directly so that then if they do want to move into a sales leadership role, they've already kind of got that tool in their tool bag.

Jessica Ly: Oh, that's interesting, but good point. You're right. Just because you're a phenomenal sales rep doesn't mean you're automatically an excellent manager. Yeah. I want to ask about the role. The best practices as far as like the career tips, right? Gaining visibility, gaining respect, gaining the funding for sales enablement. Talk about that.

Glenn Clark: Sure. Um, you know, it's one of the more exciting aspects of my role, but also one of the more challenging, I mean, when you boil it down, enablement and a lot of cases, is a money spender. And but we are influencing the money makers. And so there is a balance of how do you help sales leaders understand that through enablement and investing in enablement, it actually is going to read a ton of dividends with the sales team. Most sales leadership understands the value that sales enablement brings on a certain level. But it is that level of understanding and appreciation that determines how much investment they're going to make in the sales enablement team. Unfortunately, here, I have an amazing sales leadership team that totally gets the value that sales enablement brains. And so part of that even as we've grown came from when I came on board, one of the things that I wanted to ensure early on is that you've got somebody that has sales experience, you've got somebody that has a ton of expertise, take advantage of that, by having sales enablement at the table. When sales leadership is determining to go to market strategies when they're determining how they're going to structure the team, take advantage of sales enablement and their expert expertise to be an additional perspective that helps shapes that thinking. And through that, there became this trust that happens with I do see sales enablement as an extension of the sales leadership team. And so once you've kind of got that going, and you started to build that relationship, and then brand, you have to keep that up and save to keep adding value in terms of the programs that you're offering, your understanding in the business, your ability to align with what sales leadership feels is necessary. And so that's one of the things that I think is really important is outside of building your brand. It's around aligning with leadership and making sure that you're gaining their buy-in. Because if you don't have sales leadership buy-in it, your idea could be the most amazing idea, but it will die on the vine because you won't have the support. And so why I've learned sometimes through some hard knocks that get leadership involved early, get their buy-in, put your in some case, you'd like to put your pride your ego to the side, and know that if you can support the sales leadership team on their vision, then that benefits you as well. Because when you are looking for programs, you're looking for additional money to offer some consulting or to invest in the sales leadership from a training point of view or to buy a new tool. Leadership thinks about that. Like, how easy is it to do business with the enablement team? How aligned are they with what we're trying to accomplish? And do I trust them to be able to execute and deliver and make a difference if I make these investments in them, and so I'm fortunate to say that we have a really good relationship with sales leadership, and sales leadership consistently makes investments in enablement, which makes my job more exciting.

Jessica Ly: Now, looking ahead, 2020, I know you only do the 400 direct sales reps, but what about partner reps, you know, and are leveraging enablement content to help the partner succeed or to customer success people to upsell or cross-sell.

Glenn Clark: So I think in a perfect world, at least as it pertains to where I am, there are advantages to a centralized enablement organization. And that centralized enablement organization is supporting the customer success team supporting the channel team supporting the direct sales rep supporting the inside sales team. But that's one of those things where you have to kind of grow into that because, as I mentioned earlier, we have a lot of things that we're doing to be successful in the marketplace. And we're doing it rapidly. And so when in that type of environment, folks are may come to a conclusion, I mean, not one person, so I'm just going to build a headcount for them and get the headcount of them and I'm just going to have that person start enabling this team. But what happens in that environment is kind of what we talked about earlier on the siloing is that you might end up with some duplicative efforts, particularly if you're trying to align your Customer Success folks with your sales folks, or you're trying to align your selling motion that sales leverage with how channel partners sell. And so what my proposal is, is to really have this centralized enablement group because although they'll still support those individual lines of business, it's done through a connected strategy. And by doing that, these folks that are enablement can actually do more with less because now you're not creating duplicate work. You're actually taking advantage of some of the work that's been done some of the expertise as you ultimately look to drive that closer connection between customer success and sales, or sales and the channel partner team.

Jessica Ly: I totally agree with that. And looking forward to seeing how you do that. We actually, you know, agree that there shouldn't be silos in content enablement, whether that enablement is for your direct sales team, your partner's customer success, even prospects who are looking for contact, right. So Absolutely. Well, this has been a great conversation, Glenn. I appreciate you being on the show and sharing your thoughts and best practices.

Glenn Clark: Absolutely. It's my pleasure.