Episode 260: Jay Shephard on Creating an Effective Enablement Charter

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

Today, I’m excited to have Jay Shephard at Bentley Systems join us. Jay, I would love for you to introduce yourself, your role, and your organization to our audience.

Jay Shephard: Thanks for the invite. I’m thrilled to meet you and spend some time with you. Where do you start? I have been doing this for a while. I started my career 25 years ago selling, and when you start your career in selling you start to pick up some things that seem to go well. All of a sudden I started being asked to do some coaching with new hires that were coming in by my boss. What I found out, Shawnna, is I loved it. It’s a lot of fun.

I thought, is there a career around this? I love selling, but I also love the coaching element. That’s how I kind of, we’ll call it backdoored into this thing called enablement. Specific to enablement, it is an evolving picture, which I’m sure we’ll get a chance to talk a little bit more about.

I’ve had an opportunity to work primarily in the enterprise software space in both sales effectiveness tools as well as software platforms. I started with Bentley in 2023 and really took on a very cool challenge and that was to redesign, revamp, and repurpose enablement to be more of a strategic aligned value add to our CRO. That’s where I am today.

SS: We’re excited to have you here, Jay. Now, a key focus for you at Bentley Systems is really, as you’ve stated in your intro, reframing the way that your organization thinks about enablement. From your perspective, what are some of enablement’s core responsibilities and what is the value that it brings to the business?

JS: I think enablement, the industry, the space, whether it’s in the United States, Europe, or Asia, doesn’t matter, it is in flux. In other words, if you ask 15 people what the definition of enablement is, you can get 25 answers. When it came to coming to Bentley, what we figured out early on was the fact that there is this talented group of people that make up the enablement team, but they were misunderstood. They were almost pushed into a corner and almost like enablement became the department of broken things, as I always call it.

They were an afterthought. It was the last thought, like oh yeah, we better get enablement involved. Well, that’s really not the purpose of enablement, but it was created to be that way based on just general culture and a lack of definition of the value of what enablement brings.

SS: Jay, I know that you created a sales enablement charter, which really kind of focuses on outlining the mission, the goals, the strategy, and the responsibilities of your enablement function. Tell our audience more about this. What are your best practices for creating an effective enablement charter?

JS: I’ll start off by saying the reason I went to Bentley. It had everything to do with the CRO. He wanted to lead a transformation project, initiative if you would, company-wide to drive the strategic value of Bentley Solutions to their end customer. The CRO realized that there were some significant gaps in there, which of course was enablement.

I took this position first and foremost because it was aligned with the CRO. I think that’s really important for your listeners to know. The CRO is critical to the direction, as well as the strategic value of what enablement brings. Knowing that, connecting with our CRO as I did through that interview process, I knew this was an opportunity I wanted to take advantage of.

Knowing that we were going to start from scratch, we went out and essentially asked individuals who were key to the business all throughout the globe, 1, what is your definition of enablement? You would not believe how many different definitions I had. 2, what are the current challenges here? Why are we not winning business? Why are we winning business? For that matter, what are the opportunities? We then used that information to build a charter that was strategically aligned to not only Bentley’s business priorities but also the CRO’s MBOs.

We built it from that perspective and then worked backward. Here are the metrics that we knew that we needed to hit to drive the priorities and the MBOs of the business. How do you design enablement to make that happen? We literally created functions as well as areas of responsibility to help drive those initiatives, those metrics, if you would, and of course, that strategic alignment, which was so critical to the CRO and myself.

SS: Absolutely. I love those. Tell us a little bit about your perspective on how an enablement charter helps to drive alignment with the broader organizational strategy and the objectives of your company.

JS: Since I have been here I probably have had no less than 50 conversations with people asking me, what does enablement do within Bentley? These are Bentley employees. First and foremost, that charter that you’re talking about, the reason it is so important is to ensure everybody’s on the same page in regards to expectations and what the possibilities could be in working with enablement or us working with that particular function of the business. That to me sets in motion a transparent relationship of our capabilities and what it is that we can deliver.

Anything you do when it comes to a charter has to be very clear in communicating what it is that you do, what you’re capable of doing, what your capacity is that you can be doing, and here’s how you are measured.

SS: It’s amazing to achieve that level of alignment. Jay, how are you driving strategic buy-in of this charter with your key stakeholders and in particular, perhaps some of your executive leaders?

JS: Well, first of all, executive leaders are measured just as well as enablement is measured. If we can align our agenda to their agenda, then we are in partnership. One of the first things that I did was I reached out to all of our global leaders and understood a little bit more about what their metrics were, what they were measured by, and really what the gaps were. Once we identified those gaps, we discovered ways that enablement could close those gaps.

Let me tell you something, when you can help someone else achieve their objectives, you don’t have a problem getting a phone call returned. That’s where they knew that I was working towards helping them with their agenda. I can tell you this team immediately got the credibility and the opportunity to drive value far more than they’ve been able to up until that point.

SS: The buy-in that you’ve been able to secure at Bentley is fantastic. Now, since Bentley is in a rapidly evolving business landscape, how do you ensure that your sales enablement strategy remains adaptive to emerging trends and industry changes?

JS: Well, that’s such a great question. Asking it in a different way, it’s almost like the old belief that when you train someone, they’re automatically trained. You never need to touch it again. We know you and I both know, Shawnna, that’s not true. To ensure that your enablement strategy and alignment are real, you have to have a continuous conversation. You have to be able to ensure that it’s not a one-and-done type of relationship.

For me, anyway, I have ongoing, anywhere from between two and four-week conversations with all of our respective leaders across the globe. I also have a similar relationship and frequency of meetings with the CRO. Here’s what we do that I think is uniquely different. I’ve taken my team and we have geographically dispersed ourselves from a coverage point of view. I have, for example, a European lead. I have a US lead. We’re going to be bringing on an Asia pack lead and so on and so on.

Because of that coverage, we now are closer to our customers. We are consistently asking not only in our coaching work that we do with them or the training work that we’re doing with them, we’re constantly getting feedback in regards to what’s missing, what we need to do differently, and so on and so on. We’re not necessarily looking for negativity, what we are looking for are opportunities to improve.

SS: Along with the adaptability of enablement, it’s also important to ensure reps are adaptable to change as well. I know a key way to do this is through coaching, which is an area that you have a lot of expertise in Jay. What role does coaching play in your enablement strategy?

JS: Coaching is critical. In fact, I would even say I put more of an emphasis on coaching and implementation than I do the training itself. Think about this. It doesn’t matter what generation you are in. If you’re millennial, if you’re Gen X, Gen Z, I don’t care. I mean, what’s the newest one now, Shawnna? I think it’s Generation Alpha, but I don’t know if they’re even in the workforce yet.

My point is they all learn differently. Some are attracted to badging, some people are attracted to microlearning, and some people want a dissertation with all the details. Then you got the audio and you got the visual and the kinesthetic elements that go into learning and transferring knowledge. That’s all well and good, and yes, you need to touch on some of those elements, but coaching is where it is applicable. You take that learning and you apply it.

It’s so different from reading a book. I don’t know about you, but I love to read. I’m always reading, but I always have that challenge that everybody else has too, like you just read a chapter, what did I just read? Right? You have to come back and reinforce it, revisit it, and that’s what coaching does. I would say that probably makes up 70% of our actual work is applying the learning that they picked up, either through a white paper, through micro-learning, through some type of course, or maybe even an assignment that they needed to reach out to, or we’ll even use learning where we’re using both virtual and live training as well. Trying to tap into not only how we learn, but most importantly, how we retain and sustain.

SS: Absolutely. To that point, to drill in, one of those areas where you coach is your sales methodology. You mentioned that having an integrated go-to-market sales methodology is a key focus for you next year. How does a methodology help drive alignment and consistency, and how are you bringing this to life at Bentley?

JS: A couple of things. We’re actually going through that process right now. The first thing we did not want to do, despite levels of background experience and experience, was pick something out of a box or go into a padded room and say, this worked for me here, so therefore it’s going to work here. There’s a lot of great methodologies out there. In fact, just pick one. If you focus on whatever you pick and reinforce it properly, I’m going to tell you something, you’ll have success. It may be measured that success, lower or higher doesn’t matter, but the key point here is to pick one and then deliver on it and coach to it. You’ll have success.

Now that all being said, we are going through the process right now of selecting a methodology, but we’re not doing it in a box. We involve people globally at all different levels of the sales process and role, and they have now made up a series of advisory teams. We created some decision criteria, collectively, and we are now going through a series of discussions with various methodology providers.

Bottom line, though, Shawnna, it’s not a decision that Jay’s making. It’s not a decision even the CRO’s making. It’s a decision that is based on a group collaborative effort where we come to a consensus. That, to me, I think is critically important. Everybody that you and I have ever worked with in the world of sales has been through training and has also experienced that training of the month club. It works. We’re going to try something different. Now, we can’t afford to do that. Why not get the collaborative buy-in from the beginning, that’s exactly what we did through this process.

SS: I love that you’ve built a committee around that. Last question for you, Jay. How do you envision your enablement strategy continuing to evolve in the next year and beyond?

JS: That’s a fascinating question because I am not one that has patience and I would imagine, Shawnna, you in sales, and anybody else in sales, you totally get what I just said. We want to deliver now. Probably the greatest challenge that I have in my career is to actually take a deep breath and understand you’re not going to create everything and change everything within a period of time, three months, six months, even a year.

Our strategy is built all the way out through 2027. Now, let’s be honest, are things going to change? Absolutely, they’re going to change, but at least we have a direction and a target in mind of where we want to be. Then you work backward to make that happen. That’s exactly how we will continue to evolve.

You’ll do that as well through these advisory teams, through that give and take and the feedback that we get from our various regions all over the globe. The bottom line is, if you listen, everybody’s on the same page. We all define enablement the same way in what we’re trying to do. Buy-in, as well as moving towards that target, just isn’t the issue that it used to be.

SS: Wonderful. Jay, thank you so much for joining us today. I appreciate you sharing your insights.

JS: You bet. Nice to see you again.

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

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