Episode 9: John Dougan on Team Structures for Sales Enablement

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

We are welcoming John Dougan to the podcast today. John is the director of global sales and productivity at Workday and he has spent most of his career helping organizations grow revenue through sales enablement. He is here to talk about some of his advice to build sales effectiveness. Hi, John. We are glad to have you.

Let’s just go ahead and dive right in. I would love to start asking you a few of these questions. We are going to start out kind of broadly. We are definitely seeing a lot of visibility and necessity for sales enablement. Do you kind of see this momentum continuing, and where do you see things going in the future for the discipline of sales enablement?

John Dougan: That’s a great question, Shawnna. I think it is probably different for every organization, and the reason I say that is, having been a consultant on the side of advising, selling, and delivering enablement solutions and subsequently moved internally with Workday, we are at a different place than many of my other friends who lead enablement functions are. So, Workday has been a real challenge. As an organization, we have been incredibly successful based on our product. It has simply been different by design and, as a result, a competitive differentiator for the last five to seven years. Our sellers have been very successful using a product-centric sales approach.

I think the early version of sales enablement that existed at Workday was really a sales training organization that gathered best practices and then tried to scale and repeat those across the organization, which is valiant and was a needed area of development for the company. I think over the last 18 months in my tenure there, one of the biggest changes in sales enablement has been we’ve moved to exactly that. We moved to a function that no longer is just concerned with the knowledge and skills that are required by our sellers, but moreover, the environment that they exist in, the processes, tools, methodologies that they use. And then also the bit that probably excites me the greatest: the motivation side, so, the sentiment, feeling, and emotions that are part of the everyday lives of sellers. So, that’s the shift that I’ve experienced over the last 18 months. Do I see that continuing to evolve? Absolutely. I see segmentation by sales enablement being the next wave, as in almost delineating what in particular sales enablement professionals are really experts at.

SS: That’s actually a great segue. I would love to dive a little bit deeper into that, though, and actually understand from you, what are some of the segments that you are seeing evolve in the market?

JD: Shawnna, when I look at my team, let me give you the delineation and what it looks like. So, I run the front office enablement team at Workday, and that basically means that we are the diagnosticians who are helping our sales leaders define the opportunities, the problems, and the needs that they truly have. Beyond that, we are also helping our design team, which is part of our back office, really establish what the core learning objectives are. I think it is an old consulting rule of thumb. What problem are we trying to solve? Why are our guys currently not doing it and what are they going to do differently as a result of it? So, my team is responsible for the definition of what that looks like, and then a help in the design stage, but then the delivery stage back end. So, we are the guys that touch the field. Our back-office team does the instructional design, the communications, the events, and the cultural component that accompanies that. So, that’s the delineation that’s happened in our sales enablement function within my team specifically, and these are guys who are striving to be experts.

And what I will say is more recently, I’ve stopped hiring enablement professionals and actually hired people who are in the field who want to do something different, or have a natural penchant to help people be better at their jobs, whether that is through coaching or whether it’s through establishing best practices or whether it’s through just setting a blueprint for what successful activity looks like. We started to bring those people in. So, those are the guys that offer the expertise around context and relevance and sentiment to the field. And I’ve got one person who does that in sales leadership and one person who does it for our AE audience.

The other segmentation outside of that, I think, is there has to be somebody for systems and tools who really has a focus on the technology stack that is being used and how it’s being received by the field. There are process and methodology, so whether or not you’re adopting account planning, opportunity management, someone needs to manage those in terms of how they fit together. We have our own sales methodology, which has been really a collection of what the best people within Workday do in terms of serving our customers and providing them with effortless experience and overall satisfaction.

I’ve talked about us being a product-centric sales organization for many years. There is no doubt about it. Our new focus is all on customer centricity and intimacy, and that’s a big shift. So, I think the person who owns sales process and methodology certainly has to have a finger in that because it’s the way you account plan and think about winning customers for life, the way you manage opportunities in terms of always adding value, always adding insight, understanding the goals, pressures, initiatives, obstacles of the organization you are selling into. I think those are core components of moving to a customer-centric model, and sales methodology and process own that.

Then we have what I think has been probably the oldest role in sales enablement and I’m saying this because this is your archetypal, old-school sales trainers who came from this vein, and certainly having sold SPIN and been part of Huthwaite and the Miller Heiman ecosystem, the third component is intervention programming. So, this is people who solve what comes up and they offer a core advisory service. So, as you well know, salespeople like to circumvent about what the actual issue is and the problem they are trying to solve. They often give you a lot of symptoms. Someone has to own that advisory component of helping them really, really define what their problems are, and that falls within intervention programming. Then I’ve got the different roles that sit within our organization and an expert for each of those. So, RSD which is our front-line manager; RVP which is our second-line manager; corporate sales development which is more of our inside sales team appointment setting SDR function, someone who looks after that; and then regional leads because I think it’s very important to understand that it’s not a one-size-fits-all for enablement. It has a regional flair. It has regional components that are nuanced and specific to the audience that you are tailoring it to. So, that’s the overall breakdown of my team.

I think within that there is probably a lot of expertise. I think assessment is one that I’m incredibly passionate about, Shawnna. I like the idea of having performance metrics that we measure people against and then beyond those performance metrics, also having behavioral indexing or indices that point to both the leading indicators from a new hire. We sell ERP, right, so at the end of the day, we can only do leading indicators to suggest how successful a new hire is going to be over the first ninety days of their productivity sprint, which is our Sales Academy. But beyond that, if you have been here, how are we measuring against pipeline generation, how are we measuring you against what you did last year, how are we measuring you against where you are year-to-date? Then, what does your pipeline coverage look like, what is the daily velocity that you are doing – all of these things – what stages are your deals in? These are all things that many people in sales enablement will measure. Beyond that, we also need to understand how the utility that salespeople place on the activities they are asked to conduct. We need to understand the confidence they have in executing against them. And then the third layer of that behavioral piece is their motivation to actually do that as part of their job, and that’s the final part of expertise. I’ll take a breath now.

SS: That’s an amazing answer. And I want to circle back on some of the core metrics and KPIs that you feel sales enablement professionals need to measure. But before we deviate away from this conversation around how we structure sales enablement teams, I’d love to look beyond your team and how you guys report up into the larger organization. At Workday, do you guys currently report into the sales side of the house, the marketing side of the house, or directly into the C-suite?

JD: So, I’m going to give you the answer, because it kind of answers both of your questions. Because from a metrics perspective, I actually believe our operations team have a core responsibility around the performance piece and we have one around the behavioral piece. The only reason I say that is because we report directly into the SVP of sales strategy and operations, and that person is the right-hand man of our chief sales officer. So, our chief sales officer or chairman of sales, depending on what way you want to look at it, has three direct reports. He has the SVP for North America sales who reports into him. He has the SVP for EMEA and APJ who reports into him. And then he has the SVP for sales strategy and operations. And underneath sales strategy and operations, and I actually think this is where Workday are sophisticated, there is a three-legged stool that looks at sales efficacy in its entirety. Those three legs are global sales enablement, which is the team I sit in; there is global demand generation and industry; and then there is global sales operations. And global sales operations is broken into three regions: APJ, EMEA, and North America. So, at a peer level, there are VPs of all of those three areas and they all report into our chief sales officer.

SS: Got it. That’s amazing, and that is very sophisticated. A lot of sales enablement professionals have also been talking about, and I suspect it’s in slightly smaller organizations, the need to have a seat at the executive table. Do you feel at Workday that you guys have that through your SVP?

JD: I do. I’m trying to understand if there’s any subtext to your question there, Shawnna, because it is a layered question and I think you could answer it a few ways. I think there are lots of people who get bogged down in the apparent strategic necessity of their role within sales enablement, and I think there’s a misnomer there because sales enablement by very definition is a strategic function. But often they need to act quite tactically and I think if you feel fulfilled and valued, and maybe it is a request for advisory services, maybe it is a request to lead and own certain initiatives which touch the field organization. At Workday, we are incredibly well connected to our chief sales officer in every sense, from an advisory component, from a definition of misdiagnosis that happens within that function at every level that’s cascaded. Just our overall OKR alone is ensuring that the skill set, tool set, and mindset that is adopted by our field organization is completely customer-centric and reflected in our sales culture. That alone is a strategic initiative that we all need to solve.

We are very fortunate in that we have a large group of people who are contributing to that. There are 35 people in our sales enablement function. The extended legs of the stool that I told you about – demand generation, industry, and operations – are also contributing to that. So, although the entire group has shared OKRs that contribute strategically to the organization, there are people within that who have a tactical role to play. You know, sometimes decisions are made and ownership is aligned to different areas of that stool and you’ve got to play the role that you have. It’s just a difficult question to answer because do I feel my role is strategic? Absolutely. I have phone calls with our GVPs and SVPs and meetings with them every month. So in terms of connection and proximity, I feel that. But make no mistake, our job is the job that is needed when it is needed. We are in servitude to a field organization. Maybe I am just not privy to not feeling like I’m part of a contributing organization, and I certainly don’t feel that I need to argue or prove up the strategic value of my role. At the same time, I have no problem executing and getting down and getting my hands dirty. So, I don’t know, Shawnna. Maybe I haven’t answered your question well.

SS: No, no. Absolutely. I think you are in a unique position from some of the other practitioners that I speak with that don’t necessarily feel like they have the ear of their executive team or support for that matter.

JD: I’m not saying we don’t get frustrated with them, Shawnna. Don’t get me wrong, right? I understand the frustration that many people would go through and I think in smaller organizations if you weren’t connected to the C-suite, I can see where the challenges lie because you are constantly competing for the eyes and ears of the audience that you serve. And as we know, leadership buy-in to win the hearts and minds of the field is incredibly important. We have that because I actually think the culture of Workday is just great people always wanting to do better, and that’s something you cannot create in a vacuum, so they need that exposure. And it’s also something that can’t be created overnight. That takes time and luckily I joined an organization that was already there.

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

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