Structured Mentoring to Boost Sales Success

Jessica Ly: I'm here with Ben Harris, who is head of sales productivity, part of the sales enablement team at Outsystems. Ben, welcome to the show.

Benjamin Harris: Thank you so much, Jessica.

Jessica Ly: Outsystem has over 1000 employees. You guys have grown because you make a platform for those software developers. Talk to us a little bit more explain what is it that you offer and some of the trends that you're seeing?

Benjamin Harris: Absolutely. So as you said, OutSystems is a platform for application development for both internal applications that companies might use for their employees, web-based applications or applications that our customers or partners might access as well. And so we're a platform holistically for that, and much more.

Jessica Ly: Okay, and as you're growing and you're bringing in more salespeople, you're in charge of making sure that they are thriving and achieving certain KPIs. Talk to us about some of the indicators that you look at, the leading indicators, the lagging indicators?

Benjamin Harris: Sure, absolutely. So from my perspective, sales rep productivity is really about not just the onboarding of the reps but helping them to be successful long term. So we look at things like how long is it taking reps to get to their first closed deal? How big a pipeline are they building? How long is it taking them to close? The first large deal? How long is it taking for them to close their first new logo, you know, accompany the houses since hasn't worked with before. And a lot of those are the lagging indicators that happen when really good things happen at the beginning like I'm building a really solid pipeline, I'm, you know, contacting customers in the right way, I'm presenting the OutSystems platform in the right way. And those leading indicators lead to the results that we're looking for.

Jessica Ly: Okay, so tell us then, how do you help them achieve a much shorter time to the first deal or time to the big deal? You know, what is it that you do to make a difference.

Benjamin Harris: We have a really amazing enablement team. So it begins with, you know, from the time that managers are interviewing, we helped to kind of set up what the right things to interview and look for should be in the right people that we want to get on board, right. So everything that we do kind of feeds that loop. And so, we have a consistent loop. But once we get the right people on board, we have a really solid enablement program already. And we're in the process of building a mentoring program, a really structured mentoring program. So Jessica, if you've ever been in a mentoring program, a lot of times you end up, you know, getting assigned a mentor, a mentor assigned to you, and maybe you get on a call, and then you think yourself, what should we talk about? It's kind of maybe a little bit awkward. So we have a really structured mentoring program that we're building out that will allow folks to know what I should be talking about on a regular basis. So in their first 90 days, which is our real key time with a new hire, they're getting a lot of content, they're getting really solid on the job training through a mentoring program, as well as very structured pieces around pipeline generation, around deal coaching for a lot of their first deals to help them be more successful on those deals, and so on.

Jessica Ly: Okay, well, this is a structured format, but how do you know that this really works? You know you do have a way of gathering the data and make data-driven decisions. So as far as what content that's further.

Benjamin Harris: Right, I think without the data, the type of job that I'm in and productivity makes no difference, right? You've got to really know that these things are taking hold and are helping folks; otherwise, they're not productive. So we are just kicking off a lot of these programs. And so we don't have, you know, a lot of structure. We have the structure in place to get the data. We don't have the data yet. But I have done these types of things on previous companies that I've been with, right? And so I've seen when you implement things like this, you can get, you know, increase a rep’s productivity by two to 3x, just by implementing some of these small three things upfront.

Jessica Ly: Okay, maybe you can share with us that based on past experience, what have you done exactly to make a difference?

Benjamin Harris: Sure. So, again, it's about being very structured, right. So, for example, in a mentoring program, a structured mentoring program, what you might want is, at the very beginning, you want people to know how to effectively generate a pipeline if you wait 90 days to teach them how to do that. You Last a whole quarter of potential productivity with new hires, right. And so what we do is we have them first do a lot of pipeline generation type of activities and modules and demonstrate that knowledge through teach facts to their mentor or teach backs to myself and folks on my team like me. So we kind of start there. And then what we end up doing is very specific shadowing, right. So I'll have a mentee, a new person in the organization, actually shadow someone who's going on a first call, and talk about what went well, what could have gone better, and then shadow someone else who went on a second call, not only are people getting kind of the techniques down, but they're also learning from a lot of different people who are already successful, right? Who already have shown success doing these things. And so, to me, a lot of it is just about being very purpose-driven with everything that you're going to do. So start with generating pipeline, and then move to discovery and qualification, and then move to, you know, kind of through a standard sales process, right, and move through all the steps. And then eventually, you get to a point where, you know, in the first 90 days, hopefully, a rep is either really close to closing their first deal or maybe I've seen it even occasionally already closer for still because they followed the process.

Jessica Ly: Okay, you know, I was like, as if thinking about, okay, you've got things that you should be doing, but they're probably things that you shouldn't be doing, maybe you can share with us tips on that, what you've seen in other organizations, things that they've been doing that you would say that is not best practice at all, like don't do that.

Benjamin Harris: I think people do a really good job in this kind of world at building the programs and structures and things that need to happen, rebuilding really good training. But what we forget is, what about all the other things that hit a sales rep’s time, right? So, for example, we forget about automating processes, right? We did sales reps have to do deal reviews with their manager, every company I've ever been on, right? That's part of what they do. And if you don't help a rep to automate that to kind of get that is going in a very easy way, it becomes just extra work, right? So then they're putting stuff into their CRM, and they're duplicating that in a deal review, and then they're duplicating it over here and forecasts. And so, you have to find a way to automate all of these things. And that is really when you tie together that efficiency, then and plus everything else we've talked about, that's where you really get to that sweet spot of productivity.

Jessica Ly: Yeah, I'm glad you mentioned that. And that's a great example of how you need to remove the friction so that you're not wasting their time doing research, putting reports together. They should really spend that time kind of prospecting activities. Right?

Benjamin Harris: Right, exactly.

Jessica Ly: So I think content is another area where I find that some companies haven't made it so that content is readily available at the fingertips for the sales rep to use when they are prospecting. They need to share valuable information, right? And salespeople end up having to go in and just like research, where's that PDF? Or where's that case study? Or where's that, you know, ROI asset that we have. So just having content at their fingertips or even suggesting I think about bite-sized content that has been somehow intelligently monitor and then served to the sales rep.

Benjamin Harris: Absolutely. I totally agree. And so, having the right tools in place to do that, right. At Outsystem, we have a high spot currently. And it's a great system that allows us to do a lot of things with content, and including serve content up to our customers and customize that for our customers when we're delivering it to them. So I think the right tools, tying together the tools and the content at the right place and the right time are crucial. I totally agree.

Jessica Ly: Okay, Ben, you know, one of the challenges is actually measuring the impact of your sales enablement work tracking that so that you can actually see the results and then take that ROI and justify further investment, whether it's in more staffing or in tools. Talk to us about that. How do you actually measure and track and justify more investment?

Benjamin Harris: I think there's a well-known model out there. It's called the Kirkpatrick model. And it really takes, you know, training and the activities associated with training, and it walks through force, really four steps. Some people say five, but it's four steps. How do we show that training leads to productivity? And it's a famous model, you can find it online. If you look for the Kirkpatrick model, it was created a long time ago, like the 1960s, by a gentleman by the name of Kirkpatrick. And so, he really has four steps to measuring training effectiveness. And so the first step is the reaction that the people have to the content and the training, right? Do they like the content? Did they like the training? And you can do that with a simple survey? Right? Did you just survey folks on the content of the training? Did they like it? That’s level one? Level two is, did they actually learn something so generally to apply that to our organization, we'll do testing, or we'll have folks record they are giving the pitch or something, and then reviewing it, right? So it's the first reaction and then learning. And that's where most organizations kind of stop. We’re like, they like it. And they seem to learn something. So we're good. But they're really only getting halfway through the Kirkpatrick model. So the next piece of the model is behavior. Are they actually changing their behavior because of the training or content that they've seen or received? And so that could be things like the pipeline generation, that could be things like that, we see them changing the way that they deliver the message, right. And that is usually tracked via some sort of review with management or some sort of skill will type assessment with a manager with someone else. And then the final piece is the results, right? So if you've learned and you liked it, and you learned and you changed your behavior, then is that also leading to the actual results, like people hitting their numbers, people doing the things that you want them to do getting the right mixture of sales in their numbers. And so if you do all of those right, and it's a really straightforward model, it's pretty cool. And I've been familiar and advocated for a long time. Now, I think it's really the go-to for any type of enablement. LND training type works like this.

Jessica Ly: So I take it that you've been able to convince management to invest further in building out the sales and management team and also the tools for.

Benjamin Harris: Yes, we have for the size of our sales organization. We have a fairly large enablement organization right now compared to many organizations I've been at. And that is because historically, they've been able to prove these types of things, right. And when you can put numbers and real dollars behind it, you're going to get the resources you need because that's how you prove it, just like we would do with salespeople. If we would do that with our customers, we would want to show real dollars that they can save the right real ROI that other customers have received. And if we do that same type of thing and have that same mentality internally, you'll get what you asked for most of the time.

Jessica Ly: Great. Well, I look forward to seeing more content from you after you've implemented this program at Outsystems. For a while, come back and tell us the stats. So the last question for you. What are you looking forward to doing in the next couple of quarters?

Benjamin Harris: What am I looking forward to doing? Well, we've got kickoffs next week. I’m looking forward to getting through kickoff. And I would say really, the most fun part of my job is helping reps new reps, especially but any reps in their opportunities, not just fly on the wall with training, but actually getting into the weeds and helping reps figure out the right questions to ask and the right things to do. That's what gets me excited, helping them be successful. And that's what I expect to do in the next three to six months.

Jessica Ly: Excellent. Well, thanks for being on the show Ben to talk about Outsystems and sales enablement.

Benjamin Harris: Thank you, Jessica. I appreciate it. Have a great day.