Episode 16: Hillary Anderson on Creating a Culture of Learning

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Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO Podcast. I am 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 they can be more effective in their jobs. Our guest today is Hillary Anderson, senior sales enablement manager at Host Analytics. Hillary, it’s great to reconnect with you. Could you take a moment and introduce yourself?

Hillary Anderson: Yeah, for sure. So, my name is Hillary Anderson. I work for a company called Host Analytics. We are in the enterprise performance management space and our tools help companies with their various financial budget processes. Forecasting, making sure that we can help them with planning, modeling, consolidating and reporting. I am a senior sales enablement manager there. I have been at the company just shy of two months here, and prior to that, I was over at a company called Hired.com. I started in sales there actually, and then built our enablement function from the ground up. So, that’s kind of how I landed in the enablement world. And I was in sales prior to Hired in professional sports, actually.

SS: Oh, very cool. So, you do come from a sales background. This was one of the questions that I was just going to ask, but what does sales enablement look like at your new organization? How is it structured and who do you guys report into?

HA: Yeah, so the company has had sales enablement for a few years, even prior to myself and my boss, Laura Holmes, having joined. So, we are definitely bringing more people, I guess, to the puzzle to kind of up-level and further grow out the existing enablement program. We report directly into our CEO, Ron Baden. The company works very closely alongside product marketing and sales ops. Previously, sales enablement was actually under sales ops. So, it’s kind of lived in a couple of different places at our company, but right now we’re reporting directly into our CEO.

SS: I know that there are a lot of sales enablement professionals and functions that are definitely calling to report directly into the executive level, like a CEO, because of the fact that you then get a little bit more autonomy. You’re able to make recommendations for the business across the entire go-to-market function instead of just solely focusing on sales, which oftentimes you need to look beyond them because you’ve got partners across the aisle in marketing and in customer success. So, that’s very cool to hear that they have it structured that way at Host Analytics.

HA: Yeah, I always like to say, some of the most successful sales enablement kind of acts as connective tissue to the rest of the company. So, I think when you have either great visibility at the executive leadership table or you’re working directly with your CEO, or even your CRO, it just allows for enablement to have a big impact across the business as a whole, beyond just executing on programs that might impact sales folks, specifically.

SS: Yeah, exactly. And what, if we can take a step back, what was the impetus for sales enablement at Host Analytics?

HA: That’s a great question. So, I think the company has a very technical solution, and I think prior to us even having joined, it was really important that we build a culture of learning and skill up-leveling. And, we had a sales enablement manager many years ago as well who built it from the ground up. I think that just came from a place of really wanting to make sure that as the company began to grow in scale, that as a whole, the sales organization really valued making sure that they have the skills, they have the training, they have the content and tools that they needed to be successful.

So, it’s pretty ingrained in the company’s sales culture to create a culture of making sure that you are an enabled salesperson. And that’s been really great to see how much investment there had been, even early on, beyond just being reactive and being at a point of growth and saying, “Hey, we need to get these processes and programs in place,” which is what typically, at least, I’ve seen in the past tends to be more of the common impetus.

SS: Absolutely. I love that culture of learning philosophy, that’s amazing. And I think that flows really well into some of the other things that we wanted to cover. Because at the Sales Enablement Soirée last year, you talked about the need to deliver training, content, and tools in a way that’s accessible to all of the different types of learners and all of the different experience levels. So, what are some of the ways sales enablement practitioners can go about doing that? I’d love your advice.

HA: Yeah. So, I think, at Hired I knew that it was something we needed to account for because we were really beginning to scale our business up through mid-market and enterprise. Previously our customer base had been very SMB focused, and so we were seeing a shift in the salespeople that we were bringing on board – being more of that scrappy-type, startup salespeople to being really seasoned software sales individuals. It was something that I knew I was going to have to be ahead of it and pretty proactive in making sure that our programs and our enablement initiatives were accessible and digestible by all different types of individuals.

Then I came over here to Host, and we have quite a wide variety of net-new grads, to folks that have been selling for 15 to 20 years. I’m really glad that I had to exercise that muscle before ending up at Host because I think that there are a couple of things that you have to really account for.

So, especially with different generations, people want to digest material in different ways. Some of our more seasoned or veteran salespeople like the ability, at the end of the day after they’ve done all of their work with their customers, to look through their email inbox and catch up on all of the things that they might have missed or might have come through from either product marketing, enablement, or even our executive leadership. Whereas, millennials tend to like to get that information in real time. When did we find this latest competitor insight? When did we get an update on a marketing initiative that was coming out? And they really like the ability to get that real time, and I think that’s just a generational thing.

It’s something that we think about when we think about how we want to roll out information and communicate with the field. How we want to deliver training. You really want to make sure that we’re giving people the choice for what makes sense for them and what is most digestible for them. If you have folks that are blocking out their day in terms of how they’re managing their book of business, and then you unexpectedly toss a training on in the middle of the day, that can interrupt their flow. So, we really want to be cognizant around how we’re rolling things out and training the field. That’s through a variety of different mediums, right? So, we’re trying to leverage things like video, we’re trying to leverage those email updates if it makes sense, but we’re also trying to take advantage of things that we can get to them in real time, because as I mentioned, that’s definitely something we want to think about as we’re getting more and more millennials through the door and younger people that want the ability to get as much information as quickly as possible. So, making sure you’re facilitating those different learning experiences for those different groups of people.

Then, really think through the content that we roll out and the training that we roll out being accessible and digestible by folks that have different experience levels. So, whether you have an SDR for whom this is their first job out of college, the first time that they’re in the workforce, and they really need a whole breadth of knowledge to get them up to speed in being able to actually make an impact for the business. Or whether you have someone who has the industry experience, they’ve sold for many years, and making sure that they just have the things that will help them close more deals. Just give them those extra pushes. So, it’s just making sure that you’re aware that you have different audiences, aware that people are going to digest and learn things in different ways, and then be aware of the fact that not everyone wants things in the same forum. So, the more desire and interest in terms of how you’re delivering that content, the better off you’re going to be because you’re just going to have more people on the other end of that content or that training that are able to actually make good use of it.

SS: That’s fabulous. And you kind of touched on this a little bit, just having different types of audiences that you’re trying to reach across your sales function. I would also like to drill in a little bit on the different levels of experience, and that may come from tenure or it may just kind of be a gap between just top-performers and maybe the middle pack. How is sales enablement working to reduce the knowledge gap between those sales reps? Maybe your top performers are doing one thing differently, and how are you taking that and distilling that out to the rest of the team?

HA: Yeah, so I think the first thing really just goes down to creating a culture of learning and teamwork. As I mentioned, Host Analytics had sales enablement before sales enablement was really a hot thing. Because of that, the culture has been one of sharing best practices, collaborating, and if your teammate wins, you’re winning. I think having that culture is going to be the first thing that really allows that knowledge gap to shrink because you’re going to have your more seasoned reps mentoring your younger reps. You’re going to AEs that are much more willing to work alongside your SDRs and help them refine their skills if everyone acts like an owner, which is something that was a big thing at Hired across our company.

Creating that culture of teamwork and acting like everyone has a stake in the business, I think, is the first thing. Making sure that we’re documenting the things that work, we’re sharing our stories about things that go well, but also the things that don’t go well. And really creating custom paths as a result of that information or that milestone, that certain individuals might be in their trajectory throughout their career.

I think the other great thing that you can really do is make sure that you take advantage of some of the tools that are out there that allow the team to arguably drop into the really strong calls that their peers might be having. Tools like Gong are a really great way for you to say, “Hey, I just got off this really challenging conversation with a customer where they threw out all these objections and I kind of stumbled through it. Here more seasoned sales rep or here manager, can you help me think through how I can approach this better next time?” And then leveraging that to help share it with your team and again, win together. It’s easier to create plays and a teamwork mentality if you’re sharing and collaborating together, and I think that kind of goes back to the sports mentality of, “okay, this game went well, let’s watch the film together.” How can we do it better next time? And then there’s that openness around how we can improve over time.

SS: I love that. Going back to something that you actually just said was making sure that everyone really felt like they had a stake in the business. I would love to get your perspective on what is sales enablement’s stake in the business? What is sales enablement accountable and means to deliver back into its business?

HA: I mentioned this earlier, but I think that thinking of sales enablement as the connective tissue will help drive you in terms of where you spend your time, the things that you do, where even your budget is allocated. Thinking through how you can make a big impact on the business and the things that relate to sales. So, maybe it’s initiating a new product feedback process, right? Although that might not be specifically for an ROI right from a revenue standpoint on the sales side of the house, what that could perhaps do is eliminate some of the friction that the product team might be facing, give the sales team the ability to give their customers a voice, and then start driving towards objectives of the business by way of the sales team. They are the ones that have direct access to our customers, day in and day out. So, how can we leverage that and make sure that it’s helping our business as a whole? I think that’s one aspect.

I think it’s making sure that our reps that come in the door get educated on who our business is, what’s our industry, who are our competitors, making sure that they can be a productive member of society by packaging up the things that they need early on in their journey with the company, making sure we’re helping onboard them to success. Then, I think it’s ultimately thinking through, how can we drive sales to make the biggest impact possible?

Also, from a revenue standpoint because arguably, if our salespeople aren’t selling, enablement is not doing their job. So, how can we give them the tools, give them the content, give them the training and help initiate process and communication that allows them to do their job right, as effectively and efficiently as possible? And making sure that they have the things that they need, so that when they’re on the phone with customers, they’re not sitting there having to do more work than they already do, and they can really focus both their skills, their effort and their energy on getting their customers whatever they need throughout the sales process.

SS: Thanks 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 want to know more about, let us know. We’d love to hear from you.

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