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Evolution of the Sales Enablement Charter

| 49 min read


Roderick Jefferson: Good morning, everyone. How is everyone today? There we go. Now we are alive. First of all, I would like to thank Highspot for the opportunity and for putting together this incredible panel. That topic of the charter seems to come up over and over again, so it is one of those things that I have been excited for all week and emailing back and forth and all of the online social media that comes together. Our goal is to make sure, 1) we talk about this in stages – where have we been, where are we now and where are we going as sales enablement practitioners and how are we going to get there – what are the tools, what are the vehicles, what are the programs, processes, etc. to get there.

So, first of all, I am Roderick Jefferson. I am the CEO of Roderick Jefferson & Associates. We are a consulting firm focused on sales enablement. A little bit on my background – I have 25 years of doing training, enablement, effectiveness – all of the titles that I am sure everyone in the room has carried – yes, 25 years. I’m older than I look. I just don’t tan. I’ll leave it at that. It’s always a strange reaction on that one because you want to laugh, you’re like but, “should I laugh”. And so, quickly on my background – I am a salesperson first and foremost – started out carrying a bag, moved into a sales enablement role from there and I have run enablement at Siebel Systems, Network Compliance, Business Objects, eBay, HP, Oracle, Salesforce and most recently Marketo. Some of those are going to be big someday, trust me. At least I am counting on the stock to do something. So, I would like to first and foremost thank the folks that are on the panel for giving up time and sharing your best practices. And if we could start here with Haley and just go down, take a moment and introduce yourselves, your company and your responsibilities.

Haley Katsman: Yes, absolutely. Hi, I am Haley Katsman. I work at a company called Highspot and I am the vice president of account development and I also lead our enablement team internally. I am really passionate about growing – you know technology companies in that high-growth phase. I took a team of zero two years ago on the account development team up to about 45 today and doubling every year after that. So I am really excited to share some of the internal best practices from an enablement perspective and also kind of the perspective of a sales leader – sales first and foremost – as well as some of the companies that we work with and help enable their sales teams as well.

RJ: Thanks, Haley.

Steve Hallowell: So, I’m Steve Hallowell. I run sales enablement and what would probably be called sales strategy at a lot of companies at MuleSoft, now part of Salesforce, which has been a pretty exciting part of our journey. This is the second company I have done and prior to that, it was Responsis. And a lot of where I’ve focused is I’ve seen these companies scale from the tens of millions of revenue to hundreds of millions of revenue. There’s an awful lot that has to change about their go-to-market. It impacts everything from marketing, sales development, sales, and every other part of the go-to-market operation, and that’s what I have been at the heart of helping to re-architect.

Carrie Bustillos: I’m Carrie Bustillos and I lead the global sales enablement team at Autodesk. We formed it about four years ago. I have a group of about 40 sales enablement professionals who are focused on the business of people. That is really what I view my job as. It is people and helping people to be great performers. So, we focus on making sure that we instill in our sales team and our customer success people the right mindset, help them develop the right skill set, and learn how to leverage the toolset that is going to help them be really, really good at what they do.

Hang Black: Hi, my name is Hang Black. I currently work at 8×8 in running their global team there for direct and indirect sales. So, a little bit about my background – I was for many years an engineer, then many years marketing, and then many years sales, so add those all together and it’s been a career. But it is kind of where I see enablement going – you kind of need that cross-functional translator to be able to get buy-in from the C-suite and then to actually translate it and get buy-in from the sales team because, at the end of the day, we are all salespeople.

Ryan Leavitt: Everybody, I am Ryan Leavitt. I was one of the founders of LearnCore, which was recently acquired by Showpad, so now I lead growth and strategy at Showpad and one of my responsibilities is sales enablement. So, what is really interesting about that is I’ve, until the last three or four months, I‘ve actually never been a sales enablement practitioner. But I have spent the last seven or eight years working with hundreds of you folks, hundreds of sales enablement practitioners, learning from you, and now I am leading it, which is really interesting. We have a global organization, we have four people on our sales enablement team, and I am here to share some of my experiences and learn from you all as well, so this should be a really exciting day and panel.

RJ: Thanks, everyone. So, we want to do this a little differently. So, obviously we have all been to these before and I promise that we won’t talk for 58 minutes and leave two minutes for questions, as we have seen. So, what we would like to do is make this interactive. We’ve got a list of questions that we can go through. However, I would like to make this a bit more of a conversation and find out what is important to you, why you came and what you are hoping to learn out of this from this group because you’ve got an enormous amount of experience and tenure up here. So, why don’t we just dive into this thing and as questions come, we will run the mic if we can.

So, Haley, let’s start with you. We all talk about goals when we come in, and obviously, they are incredibly important. What do you consider some of your most important goals when you are thinking through sales enablement strategy?

HK: Yes, it is a really good question. I think that from working with a lot of companies and then also leading it internally, different enablement teams will have different goals. I think one of the things that we have really noticed is that, as we talk about the evolution of the function in the roles becoming much more strategic, which is great because you can be more goal-oriented and less reactive. And there are a lot of different elements that we look at. There is absolutely that element for us since we’re such a high-growth company and we are bringing on new people on a very frequent basis. We are looking at time to first sale, so we are looking at how fast we can onboard someone. We are also looking at adoption of the content, the knowledge, the training that is actually getting used. We are creating all these materials – but are they actually getting used by the team? Are they engaging our buyers? So we are always looking to increase that usage.

And then at the end of the day, we really look at our goals being the same goals as the audience that we actually go and enable, so we are enabling not just sales but also account development, our partner teams, services and they have individual goals as a function and so we are completely aligned to whatever those goals are because we are there to support them in meeting and exceeding those goals, so we are very, very tightly aligned with each team’s goals.

RJ: How do you ensure that those goals take us as sales enablement practitioners away from being the fixers of broken things to really focusing on helping to partner and drive incremental revenue?

HK: Yes, it is a really good question because you really can get stuck in this trap of being so reactive and just putting out fires, but you have to be very intentional about being strategic, so I always talk to our team internally and say how realistically we want to be strategic in about 60% of what we are doing. Forty percent is going to be reactive. There are a lot of things that just come up and we do have to be reactive in those scenarios, so a lot of, “I loved what you said”, a lot of really great project management and prioritization, and making sure that you are hearing everything that each of the teams need. But also that you are looking at the broader strategy and prioritizing effectively so that you can meet the overall goals. And that takes a lot of cross-functional communication, a lot of project management, so it is no easy task but you just want to remain strategic as well as being reactive in some scenarios.

RJ: So you’ve got to learn to be strategic and tactical then, is what you are saying? I love where you’re going.

Carrie, I’d like to move to the next question to you and stay in line with where we were with Haley, and that is, as it continues to evolve from where we have been to where we are and especially because globalization has just taken over, how do you build a charter that supports a broad and global audience? We had a chance to talk, and if you can, just kind of outline, first of all, all the areas of your responsibility, and then how do you tie all of that together globally?

CB: I first want to react to something you mentioned, Roderick, and you and I have talked about this. Sometimes people talk about sales enablement as the fixer of broken things and I really don’t like that because, again for me, it’s about people. People are not broken things. People are amazing, wonderful individuals who are contributing to the success of your company, the success of your customers. And so you shouldn’t treat them like broken things. Maybe there are broken processes, but again I’m in the business of people and if you stay focused on making sure that you think about how to make people really successful at what you do, it is hard to go wrong. Now, as your charters expand to become more global in nature, I think Haley has a really good point that you have to stay attuned to how your business is evolving and what the needs of the business are that are shifting. It is really important that you understand your leaders – the head of sales, the head of marketing, the entire C-suite – you have to understand what is really important to the business, what are the key initiatives that are being driven and how the sales enablement function can help further those initiatives, and how investing in people and helping them be high performers is important.

Now at Autodesk, one of the moves that we have made recently is to expand our sales enablement efforts to the customer success function. Now some of you that might be more born-in-the-cloud companies and subscription models, this may be part of your DNA, but Autodesk is over 30 years old and we started out as a company selling perpetual licenses of software. We have shifted that over the last couple of years and it is important to know the entire customer success cycle and how you make sure that you are driving that entire success cycle, and that includes the customer success function. So if we are only addressing the sales piece of it, it is incomplete. So we have been expanding to cover that base too. And the types of things that we do are, again, all about helping ensure that our sales team and our customer success organization have the knowledge, the skills, the capabilities, to do their jobs really well.

RJ: Great. Steve, quick question for you, and that is, as we are talking about that globalization and we are talking about building a charter, how do you build a productive charter on the front end that has a long tail of sustainability behind it?

SH: Just picking up on the dialogue here earlier, there is a saying that all politics is local – I think that ultimately all enablement is local. Then what it is, is you think about dealing with an expanding global team. If we are not very in tune with and meeting the needs of folks in whatever region, whatever part of the world people happen to be in, we are not going to be successful. But similarly, we can’t have a dozen different initiatives going on out there – it has to come back to a central thing. So, one of the things that my team is focused on is making sure that we really have close alignment with our front-line leaders that are able to really translate through the broader goals and initiatives – how does this show up for you at the ground level at the local level and how do we make what we are doing is relevant and bring that and get buy-in from the local sales leaders. So, I think that is one of the pieces in making sure that this charter is durable. I think the other element is making sure that we are always anchoring on top of the business value. What our team is quoted on, what we wake up every day thinking about is overall sales productivity. Going back to what you said, if we are helping everybody in the field get better at what they do every day, we are going to be successful, but that provides the grounding.

RJ: Thanks, Steve. And that inherently becomes what we all do and focus on which is change management and, Ryan, I have a question for you because you are living this now. So, as you are going through that change management process, how does that impact the goals that were in place previously because we are watching landscapes just collapse across the board in multiple spaces, and because you are living it, I would love to find out from you, how is that transformation now impacting what your world was, where it is going to, and how much more important is the change management component now?

RL: Good question. So, we are currently going through an acquisition – we are being acquired – so we are going through a reorganization right now, so there is a lot of change happening in our organization and that is what RJ is referring to. You guys have all kind of hit the nail on the head with this. I really start with prioritization. You need to make sure that everybody at the C-level, the heads of each department, the head of sales, the head of marketing, head of customer success, everybody is aligned on what we are trying to do and why we are trying to do it. And then communication is really, really critical, so you need to get buy-in from every level down. So before we roll anything out to the field, anything that is going to be changed, any new processes, any new messaging, any sales motions or anything like that, we need to make sure that the leaders are also bought in on this. The leaders have to understand it, you have to train the trainer, you have to make sure they are certified and everybody understands why. If everybody ultimately understands why, you can then drive it down to the front line teams and then their managers are bought in and the leaders are bought in and everybody is aligned on the same goals and try to attack it together. Without that buy-in, without that communication, it falls, because everybody is trying to run really quickly and there are a lot of different initiatives happening.

And actually I learned, it was probably four or five years ago, I was talking to Doug Landis – he ran sales productivity at Box and he was telling me about how they prioritized. They did three certifications every quarter, and they would sit down before the quarter with the whole C-level team and they would say, “this is what we are doing, is everybody aligned with this?” And when everybody was bought in, then they would go out and execute, because if that changed too quickly, then you are rolling out eight or 10 things and nobody can actually execute on it. So, it really is that prioritization and the communication, I think, to drive really solid change management across the organization. And then the last thing is that there is a lot happening at our organization. I’m sure there is with all of you and everybody out here, as well. So enablement, and Jake, you mentioned this in your introduction, it is not just the enablement team and the sales reps; it is everybody in the organization. Everybody is responsible for making sure it is successful and then that goes back to the communication into why to then make sure everybody is involved, and we really, really try to drive that through.

RJ: Good job. So then, in line with that – and before I go on, I want to make sure I do a pulse check – are there any questions in the audience?

Audience 1: So whether internal or external as a consultant, let’s say you are chartered by VP of sales or chief sales officer or chief marketing officer, and you start talking to the regional sales leaders, and they say, “oh no, no, no, I hire professionals, they need to be out there selling, I really don’t have time for this stuff – they need to be doing real work.” How do you address that issue? And I assume no one else has seen this except me, right?

RJ: Maybe once or twice.

HB: Enablement has moved really – we have talked about enablement 1.0, 2.0, 3.0 – and it is absolutely appropriate for where the company is in its journey, but when you talk about seasoned sellers, our goal really is – I want to borrow a friend of mine’s phrase, Renee Capovilla from Palo Alto Networks – our goal is to move the middle. So, we have moved enablement from producing content to delivering content and measuring consumption to measuring application, so what I tell my people is that we have to have ways to measure leading indicators. Now, if you are at the bottom of the leader board but you are killing your quota, awesome. But if you are struggling and you need to make up for your consumption, that is a very difficult conversation. And in most employment situations outside of sales, you have that first conversation, a second conversation that says you’re going to have a third one and you don’t want to get to the third one. In sales, you have one conversation, so I tell my people that up front. We are here to make you better. Why would you not spend that 12-15 minutes a week investing in your own career? And if you have the backing of your C-suite and constant check-ins from your C-suite, then you will get the buy-in. I see a lot of head nodding here.

CB: Well, I have a point of view on this one too. I think you have to earn the right to have that conversation and to provide that solution to a sales leader in the field. And as we sit up here and talk about focusing on the priorities, that is great, but you probably have more things you are being asked to do than you have time to do, so you have to make a bet. And you have to be strategic about the move and where you are going to focus your organization because you can’t do it all. One of the ways that we did this to earn the right to engage with some of the field leaders is to focus on programs that we thought were really going to make a difference.

For us four years ago, that was onboarding, because we were doing a lot of hiring in the organization and the onboarding was not really updated over about a five-year period. And so, we made a strategic investment to bring in somebody with a very strong sales background to redesign and re-architect that entire onboarding experience for new hires and it was really good. And guess what? The sales team and sales managers saw how people who were coming through the program were high performers. They were doing better than people who didn’t go through that program. So that earned us a right to go and work with leaders in the field and talk to them about other things that we could do to help them be successful.

HB: It is also helpful – I don’t know if any of you run an enablement council where it is really led by sales leaders. How many of you have something like that?

CB: An advisory group.

HB: Yes, an advisory group.

RJ: If you don’t, I highly recommend it.

HB: That’s the best way to get buy-in, but essentially you’ve got your sales VPs globally and you’ve got some top sellers in there, so any new program that comes in – and then we invite other groups. We invite marketing, we invite training, we invite services to come in to present – “hey, we are going to roll out this campaign” – and they almost do a focus group with the top sales leaders and so we massage the program and then we say, “okay, why don’t you come back to us next month.” They come back to us and we say, “that sounds like an awesome program.” Then we go live to the field, and when the field sees it, they say, “okay, this has been blessed by the council. These guys have made club every year, I want to look like that.” And it is very helpful. That is one way you can get buy-in.

RJ: And as a consultant, coming back to your question, we are perpetually “earning that right. And so, there are a couple of things that my company does differently and that is: first of all, we start with an assessment and we come in with a set of fresh eyes and we say, “look, we’re not here to poke holes, we are not here to find out what’s wrong and fix everything. We are really here to give you a fresh set of eyes and we have some very specific strategic questions.” Fortunately, everyone on the team comes from sales and has carried the bag, so we speak that language.

I think that’s the other piece that I want to stress is, as enablement folks, obviously we’ve got our own lingo. Stop using it. Start talking in your customers’. And please, if I can say anything, I implore you, stop calling them stakeholders because they are not; they are your customers, they are your business partners, and as long as you treat them as stakeholders, that means that one of you is beholden to each other. As partners, in order to make this mutually equitable, it requires that you both have input and you both have give-and-take in this. So if you could step back and say, “okay, would I treat an external customer and would I approach them this way,” and if the answer is no, don’t do it internally. Take the same philosophy internally as well.

Audience 2: I just had a quick question – well, I don’t know if it’s quick.

RJ: Hello, Kira.

Audience 2: Hello, Rodney.

RJ: It won’t be quick. I know Kira. It’ll be deep but it will not be quick.

Audience 2: Thank you for throwing me under the bus. I know that a lot of sales enablement leaders are faced with the urgency of execution vs. quality and in many ways, there is a lack of understanding between that trade-off. How have you handled that very difficult conversation in the past?

RJ: Steve, this is a great one for you.

SH: I don’t know if I have great answers on this one other than you’ve got to do both. And ultimately it has to be both. I don’t have anything better than that, other than we’ve got to move quickly, we have to move with urgency and if the quality isn’t awesome, you lose the right to engage. I think – this is something me and my team talk a lot about – the minute we roll out something that is half-baked, we lose our audience.

RJ: Be realistic. And what I mean by that is don’t take on 17 different deliverables, because it’s not going to happen. Say, “okay, we can do these top three to five and if we do these really well, this will help move the needle.” And the old adage, “we can do this right or we can do it fast”, I think still sits in place. So find out from them, do you want this fast? Okay, great – it is going to be fast, but it is going to be iterative. It will be a pilot. We will start here and we will grow. If you want this done right, it is going to take some time, it is going to take some planning and it is going to take collaboration, and not just with sales and enablement. You’ve got to bring in all those other pieces and that’s where the orchestration piece comes in, as you were saying earlier about making sure that everyone comes to the table.

CB: Yes, I am a big believer that a few are better. I think it is easy to get stuck in the trap of trying to please everybody and trying to address everybody’s needs, and it is really difficult to do that well, and you are going to compromise. I have found that by focusing on fewer things and doing them really, really well, people are going to come to you and say, “I want more of that, I want some of that, how do I get some of that,” and then you can have a conversation about how to make that happen.

HB: I bring it back to being the trusted advisor for your customers. I go back to the sales team every single quarter. These are the 15 initiatives we are looking at. Give me three. And then we get a survey out and we say, “these are where our salespeople are suffering”. They are having a hard time with unclear messaging or they are having a hard time with Ts and Cs in the contracts, but we move the needle for them and what they think is slowing them down from closing deals.

RL: The one thing I would add to this, and this might be a little bit of a contrarian perspective, is that with the content that you are creating, if you are striving for perfection, you are going one step too far because you can continuously change and improve and perfect the content. The content is about impact and it is about who is delivering it and what value it is giving. We used to say we are not trying to create Hollywood content, right? If you have the video of the subject matter expert and they can do it in two hours and the content is great, or you could spend two days trying to make it look beautiful, maybe you just want the great content from the subject matter expert because that content may change again in 30 days, right, and so it is about the impact of what you are creating so you can get it out there

HB: Strive for better, not perfect, because perfect is going to change tomorrow.

RJ: It is good to walk away from perfect if perfect is replaced with productive.

Audience 3: Allow me to prod you a little bit there because for anybody in this room, at least from where I’m standing on this side, the worst thing you can hear is, “Steve, you’ve got to do both”, but that is exactly what your stakeholders and executive team often want you to do. I’m going to prod Haley because I’m going to ask about how do we actually make those tough priority trade-off decisions knowing that all of us have limited capacity?

HK: I think the conversations that we’ve been having around treating the audience that you are working with as a customer is just so important and I think that that will help guide you in a lot of the scenarios that we are talking about. So you practice what you preach. Do a great discovery. Why do they need what they have requested? Really understand the “why” behind it. Understand what they are looking for as an outcome and a lot of times you can consolidate a lot of these little tiny requests in a more strategic way, and that is where, if you do have a function that is looking at the entire go-to-market team, you can make a bigger impact with high-quality things rather than being so reactive with these smaller projects.

But I think that’s really the thing that guides us in the conversation. If we get a specific request, it is doing a discovery, understanding why, communicating, “this is what this will look like if it is completed in x time” or “if we do it in this time, this is what it will look like”. What do you want? They are the customer, so it’s whatever you want. There are some scenarios we run into where our VP of sales or our VP of marketing say, “we absolutely need this out in the next week.” It is an announcement. It is something extremely timely. We say, “okay, well that means that these other things get deprioritized.” Then there are other scenarios where it is like, “hey, we want to put together this whole great play around customer stories.” Well, let’s do a really good discovery with them to understand why do you want that, what are we trying to accomplish here, and can we tie that in with other things to really drive business impact?

HB: Has anyone seen the movie – this is a rhetorical question obviously – has anyone seen the movie Office Space? Show of hands. Alright. So six months ago, I was part of a company before 8×8 that got bought out, so it was public and it went private, and I was the only non-VP that got interviewed as enablement, and that goes to show you where enablement is going. So over the course of two months, I got called in about eight different times. I felt like Peter G – it felt kind of good because I met the Bobs a lot but every time it was, “am I going to get fired?” Or, am I going to get headcount? So essentially, you have to know your market. I see a lot of familiar faces in here. You’ve got some great market leaders in here. You’ve got Siobhan Thatcher. You’ve got Robert Peterson here. Learn from them. Look at CSO Insights, look at SiriusDecisions and form data-driven initiatives.

So what I did is showed up to the Bobs and then eventually to my CEO. This is what SiriusDecisions and CSO Insights say, if we have market alignment, we get 13.5% increased quota attainment. If we have internal alignment, we get 6.8% quota attainment increase. And this is not me saying it, this is what the market is saying. This is what researchers are saying. Okay, of these eight different initiatives and how it is going to move the needle, if we engage in social selling, we can increase by 33%. So if I am going to do these things, here are the priorities. Here are the different things I can do. Now here is the headcount I have. This is how I can spread them around. What do you want me to drop? And that is a very easy conversation. So it shows them, I’m going to lay down each railroad track for you but you’ve got to tell me where you want me to go. Do you want me to build one to North Carolina or you want me to build one to California? I can do it. Just help me pick.

RJ: Hey, that’s a great point because then at that point, it’s not enablement giving them what we think they need. We are actually saying, “here are the initiatives that you want driven, here is the impact they will have, and then on the back end, here are the KPIs and metrics that will come back to show your effectiveness.” Now I’m hearing a theme and that theme is productivity, right? And impact.

And so, Carrie, this is one of the things we talked about earlier and I want to circle back. We have all reported into various places, from marketing to sales ops to sales to operations, etc. Back to the impact piece, how do you think that where we report as sales enablement practitioners – and I’ll open this up to you and then to the rest of the panel as well – how do you think this impacts all of us sales enablement practitioners depending on where we are reporting to?

CB: I think that where you report into is greatly influenced by whoever the executive is that’s leading that function, and what they care about is often what you are going to be held accountable for and evaluated on. So I think it can be a really big driver of how a sales enablement team is oriented or how they focus. I think if you are able to elevate the conversation, though, as you’ve heard from several people here, to be successful in sales enablement, you have to work really well across the different functions in the organization. And to be able to engage with that executive in driving conversations about what the broader impact is that we are trying to make within the organization – not just how are we trying to move the needle in marketing, in sales, in customer success – and to seek to address those things and design programs that are going to meet the broader needs of the organization. It is not easy to do and I think it is important because, at the end of the day, you are looking at trying to drive revenue and customer success. I think that is a key outcome that you are looking for, but it isn’t just revenue, okay? So I know that there is often talk about sales productivity driving revenue, and this has been a big move for us at Autodesk. It’s expanding into customer success and taking that really, really seriously. And yes, that drives revenue too, but it does start to change the way you are evaluating the impact of what you are doing as an organization.

HB: And I don’t think it’s unique to Autodesk either. I am starting to see a lot in the market. And again, going back to SiriusDecisions, five years ago, the enablement function was reporting into marketing and then maybe three years ago, it was starting to report into the head of sales, and now we are seeing a move where it is reporting into the COO or CCO. And it is really smart actually, because it is one thing to call somebody’s baby ugly, it is really hard to call your boss’s baby ugly. So, it’s good to see that movement. If it is reporting to the COO or the CCO, your end customer is THE end customer; it is not to marketing, it is not to sales. And the COO and the CCO have customer success as part of the team, so I think it’s a really smart move and that’s kind of where enablement is going.

CB: One of the things that I think enablement people are well positioned to do is to drive some of the conversations across the organization also because it is really hard to do what you do if there isn’t that alignment – if marketing and sales aren’t quite matched. And I look at it as sort of a trust but verify. If you are getting direction from a sales leader or you are getting direction from a marketing leader, I don’t always just take them at their word. You kind of do the trust but verify and go confirm with some of the key leaders: Is this indeed the priority? Is this indeed the outcome that you are looking for? And if it’s not, you can help facilitate that alignment.

RJ: So we’ve talked a lot about leadership and influence from the executive level, and so Steve, a question for you quickly is, how do we get to that holy grail that we call executive support, and how do we ensure that the enablement charter is aligned across the entire organization? To the point earlier of the reporting to the CCO or COO – now you have to look at everything across the board, so how do you get that executive support and how do you show the value of being able to scale it across the org?

SH: Sure. You know, I think on the one hand, the answer is kind of obvious. I think it’s when you get to the next layers of it that it gets more complex. So, the obvious answer is aligning it with the business needs and driving with the business needs. But I think when you start to unpack that a bit, being able to help sales leaders see things they don’t see yet – say, “hey, here’s the next corner we need to look around, here is the next change the organization is going to have to go through to achieve our goals” – that is when you start to become a real strategic advisor to that sales leader. And so going back to the question that was asked earlier, when you see something or when your senior leader sees something, folks on the ground don’t yet see that. That is a huge opportunity to actually take what I think is one of the first most important steps in enablement which is getting the “why change?” message right.

Many of us are kind of bought into that as a way of selling that applies equally internally, and especially when you can have tight alignment between enablement and whether it’s ops or sales strategy or an analytics team, that is tightly tied into the performance of the organization. You can help diagnose – “alright, we’ve got an issue over here,” “there is something over here that’s not working as well as it could be,” or “we see an opportunity, now let’s go align the resources behind solving that opportunity.” When you start to have that conversation, I’ve never seen a senior leader that didn’t want more of that.

CB: How many people here have a sales background? This is kind of a sales conversation that you are trying to initiate within your company because you have a business within your company. You have something of value and if you can find a way to match that to the outcomes that your company is trying to achieve, you can engage in some of those conversations. I think it is also really helpful to think about what is unique about your organization, what are some of those relationships that you have that can help you further some of the things that you are trying to do. One of the examples that we have on our team is we own sales kick-off, we own the annual kick-off, and there are a lot of people who have a vested interest in making sure that that goes off really, really well. A lot of contributors across the company from your product groups, marketing, sales, customer success are all contributing to it. So we are in charge of putting that together, so that is a compelling event. It is a forcing function that allows you to bring different people across the company to drive those strategic conversations and drive alignment.

RJ: So, two final questions. Let me stop for a minute. Pulse check. Any questions out in the audience before I ask?

Audience 4: My name is Rob. I wanted to touch on the first and last word of this panel. I want to hear with evolution – what happened? Was it the sales team came back and said we need to go in this direction or was it that you did such a great job, now they added customer success or something else? Or you just came, you met Jefferson and you saw the light? What was the evolution for your particular situation to know that charter has to change?

HK: It was largely, largely driven off of success. We are growing our enablement team internally at a very rapid pace because we had such success with not only the customers, so the sales reps, the managers, even the services, partner reps, all of those people, but there was absolutely the ability to measure the success of what we were doing.

It’s a good question. There are a couple of different elements and I will kind of tie in the previous question that we were talking about because it’s related to this. When you think about the evolution of sales enablement or enablement that is even working with a lot of different functions within the organization, if you want to get executive buy-in, you need to have a seat at the executive table. And so, I report right into our CEO and our head of marketing, our head of sales are my partners. I’m working with them, I’m not working for them. And so to answer your question, there is absolutely a quantitative element to the goal. So here was the goal, the goal was set up front. Did we achieve that? Whether it’s around content, whether it’s around training, whether it’s around increasing velocity, increasing conversion, whatever it is. There is that quantitative element, but a huge piece of that was actually the qualitative element that is feedback from the frontline and from the managers, more importantly. Leading enablement internally but then also leading one of our sales teams internally, the account development team, nothing is going to get to the front line without going through my managers first.

And it’s so important to get that buy-in and then to be able to work with the partners at the executive level to tell the story, just like you would in a sales conversation, to tell the story – here was the goal, here is what we set out to do, here is what we did, here are the results, and then getting that qualitative feedback from the front line when you are actually helping them and when you are actually developing people. You will actually get a salesperson that will take time out of their day from selling to give that positive feedback if you’re doing a great job and that goes a really long way. That has really helped accelerate our function and continued to make it a function that is not reporting into sales, it is not reporting into marketing; it is partnering with those organizations rather than working for them.

Audience 5: My name is Ray. I work for Shopify. I think I have met you, Ryan. Good to see you again. I am a big believer in strengths. I believe salespeople and customer success people have unique strengths that impact the ability to close business. So for me, I’d love to hear a little bit about how you’re empowering your sales leaders to identify those strengths within their teams and leverage those strengths as opposed to treating the enablement function as trying to get people to complete learning and read resources, or rather developing them in terms of who they really are and what they enjoy about their jobs. Now, I want to caution: This isn’t a tools question, this is really a culture question I’m asking. How to get leaders to buy into that concept instead of coaching to a sales process or rather coaching to strengths. Sorry, I am long-winded, but hopefully, it made some sense.

HK: I’ll just say a quick piece about that. The culture element absolutely starts the minute that you start recruiting and then through the hiring process. If you don’t have the right people in place to do that and you don’t have the right front line managers in place to do that, then you are creating an uphill battle for yourself. So, I think that first and foremost it really starts with the people that you are bringing into the organization.

And then another element that at least we’ve seen a lot of success with is that the coaching and development that we do, whether it is myself to our managers or whether it is managers to the individuals that are on their team. Everything is very, very personalized based on understanding what are their strengths, what are their weaknesses that they might want to improve or that we might want to mitigate, identifying what we want to do with that. And then, what are their passion areas, what do they want to learn about, where do they want to go within the organization, and being an advocate for them, and then rewarding the management when they are successful in doing that. So, I think again it goes back even to the managers on the front line on coaching and teaching them, enabling them on how to do the discovery and understanding where the strengths are, where the weaknesses are, and giving them the tools – not in a technology sense but more in a skills sense – to be able to help develop and advocate for their people internally. And when you have that culture of learning and collaboration, and when you are advocating for the people on your team, that has to trickle down from the very top all the way through the recruiting process and that is kind of where you see the magic happen there. Obviously, there are a lot of things you can do, like little smaller wins, but I think that that foundation is really important.

RJ: I hate coming to these and not walking away with, “what can I go do now”. I’m all excited. Now, what do I do with it? So as a final question, if you could leave the audience with one actionable item that they can do right now when they walk out of here, 20 seconds or less, what would it be?

RL: Over-communicate. Over-communicate with all your partners, everybody in the organization, whether it’s sales, marketing, HR, CS – what are the priorities, why, and make sure that there is alignment across all their groups.

HB: I would say to gain alignment, go look at the research, go look at CSO Insights, go look at SiriusDecisions. And then form data-driven initiatives and get buy-in from your leadership.

CB: So one thing today, meet some of the people in this room. Talk to other people who do what you do. They can give you some insights into how you can advance your agenda.

SH: Have a point of view about what the business needs.

HK: I would say get a seat at the executive table from the top and then also get down on the ground and understand what your front line and what your managers need.

RJ: And I would leave with two things. One, remember that enablement is an ongoing occurrence. It is not a single event. And lastly, remember, we train animals, we enable people. Thank you all very much.