14 min
Episode 260: Jay Shephard on Creating an Effective Enablement Charter Sales Enablement PRO Podcast
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- Business
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 man
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 man
14 min