You know you are doing something right when customers advocate to adopt Highspot when they move to new companies! Recently, I had the opportunity to speak with Sean Goldie, Director of Sales Enablement at Apptio. For several years, Highspot worked with Sean while he was at SAP Concur — one of Highspot’s oldest customers. I was exceptionally excited when Highspot brought on Apptio as a new customer because 1.) Apptio is another awesome Seattle-based company and 2.) it meant I got to reconnect with Sean!
Here is the video interview, as well as the interview transcript, below:
Shawnna: Hi, Sean! I’d love to have you provide insights into why you see the sales enablement trend and momentum continuing in the market.
Sean: Sales enablement is a fantastic investment in my eyes because it’s kind of a new realm. The last ten years were really focused on the evolution of marketing technology, from marketing automation through the full marketing funnel. And now we’re starting to focus on sales velocity and how we make reps more efficient and effective. The investment time is now for sales enablement. The practice is completely changing. We’re migrating from a group of folks that used to do corporate training in classroom settings to a group of folks that have spent many years in sales management. And we’re combining a real-world skill set with the ability to teach and develop our reps, as well as integrating technology into the mix.
Shawnna: What are your top sales enablement initiatives?
Sean: Our sales enablement initiatives for the next 12 to 18 months are going to be focused on win rates. How do we increase those? What are the levers we can pull to win more? We have a finite group of companies that we sell into, so increasing win rate is important. We’re also looking at technology plays, such as the ability to enable reps to live in Salesforce by ensuring they have access to all of the tools they need from one centralized spot.
Our most important initiative this year is leadership enablement — working with sales leaders and finding ways to support and enable them better because they are really the frontline enablers and the frontline coaches. At Apptio, we are looking for ways to improve the way we support our sales leaders. That’s really my top initiative for the next 12 months.
Shawnna: How do you measure sales enablement success?
Sean: The way we measure sales enablement success is by looking at the sales numbers and the sales velocity equation. All of those factors apply to the way we look into the success of sales enablement. For example, we look at pipeline created, the number of “at bats,” win rates, stage rates — all of that. We also look at a first indicator: time to first deal, which is when a new rep comes on board, how fast can we ramp them and how fast can they close their first deal. The second indicator, which is equally important, is how fast they can close their second deal. If you just look at that first deal, there’s the potential for it to be misleading — it could have been a “blue bird” that came in quickly, or an account that was already developed — and the rep could have gotten lucky. Time to second deal is an important metric for us at Apptio.
We also factor in all of the assets that a rep uses to close deals. Within our sales learning and sales asset management platforms, we see a correlation between content usage and close rates among our successful reps. Ultimately, we look at sales-driven measurements.
Shawnna: What is within the scope of sales enablement?
Sean: That’s a fantastic question. Generally speaking, it’s important to understand what is the next wave of sales enablement. What’s the next generation, because why build something that will quickly become outdated, right? Start with understanding your landscape and where the sales enablement function is going to fall within your org. Then decide what sales enablement will cover. There are sales enablement groups that just cover sales training. There are other groups, like at Apptio, where the sales enablement group owns technology, all programs, sales kickoff and the mid-year events, as well as onboarding and all sales coaching. At Apptio, that also includes sales processes and sales methodology. That’s really a large scope compared to a lot of sales enablement teams. So, first understand where sales enablement fits within the org, and then decide what sales enablement’s charter is. For Apptio, it’s all about productivity, efficiency, and effectiveness.
Then, it really boils down to the brand of enablement you’re trying to create. Are you going to be corporate trainers? Fine, own your brand. For me, it’s really about reimagining sales enablement and all the areas we actually do impact, because we’re really the hub for marketing, product marketing, sales operations, and sales. We meet right in the middle as a very strategic function.
Shawnna: How does sales enablement get elevated into a strategic function?
Sean: That’s another great question. In order to elevate the sales enablement function, you have to understand the business more holistically. For example, I spent most of my career in sales carrying a bag. Then, I went into sales training and built the programs, coached the reps, all that. I decided I had some weaknesses in the marketing area, so I went into a marketing role for a couple years to understand marketing, the funnel, and what is involved in marketing initiatives. I also owned the tech stack for a year and a half as well.
Once I became interested in sales enablement, I knew I didn’t want to be just a corporate trainer, so I went through the business and was able to work in various functions to make myself more well-rounded. I know that’s not possible for everyone. If you don’t have the opportunities or you don’t want to take the risk of jumping into a different part of the business, you could also mentor with people in other functions. Find a marketing leader, find a sales ops person, and really get your arms around the business and learn what it takes to drive revenue. Ultimately, it’s your job to drive revenue and drive the creation of revenue by supporting the sales and marketing teams.
Shawnna: What advice would you give to new sales enablement practitioners?
Sean: Align yourself with sales and marketing. Understand where the gap is between these departments, because you’re going to be right in the middle. Then, start to understand what those people do each and every day. If you don’t know what a field marketer does, spend a day with them to understand what they’re doing. If you’ve never been in sales, then you need to get out on the field with the reps. You need to spend time with your sales leaders. You need to actually sit on calls and fully understand a day in their life. That’s the fastest way to learn. I would even recommend that you set aside dedicated time to understand these functions and say, “I’m going to shadow five calls a week. I’m going to shadow this job function and really understand what they do.” If you don’t do that, you’re really sitting in a vacuum. You’re sitting in the ivory tower of, “Here’s what my role is and here’s how I’m going to direct it,” but you have no true understanding of how those other folks do their job. Understanding — that’s the most important thing that you can do.