The Scope of Sales Enablement

Rajiv Parikh: So today, everybody, I have Jay Sherman with me. Jay, welcome to the show.

 

Jay Sherman: Thank you, Rajiv.

 

Rajiv Parikh: Jay Sherman is the director of sales enablement at HackerOne. So tell us, Jay, what is your role look like as director of sales enablement at HackerOne?

 

Jay Sherman: Yeah. So I think I see sales enablement in general, but specifically at HackerOne as kind of being a bridge between the sales and company's strategy, and then the actual execution of the sales team. So really taking what we're trying to do on a bigger go to market level, and then translating that to what it actually means for sellers in their day to day roles, but then also balance that with what everyone's asking for, what sellers are asking for, what managers are asking for. And then, on top of that, kind of providing my own insights on what I see, in terms of, you know, bigger underlying problems or trends. But in short, it's really just about helping the sales team be successful.

 

Rajiv Parikh: Yeah, absolutely. And so, how big is your sales team?

 

Jay Sherman: We're at about 70. People. Right now, across sales.

 

Rajiv Parikh: Okay. And how are you sort of balancing the demands of the sales and sort of balancing that with execution and strategy? How do you do that?

 

Jay Sherman: Yeah, I mean, I think I try to put it pull it all together, look at what we're trying to do. What are our big initiatives in 2020? As a company, how does that trickle down to sales initiatives? What does that mean for each team? But then also, really trying to have my pulse on the team on all the sellers? What are they needing? And where did they feel like they have skill gaps, or where the managers see skill gaps, and then it's not totally clean, but try to marry those try, I mean, ideally, find projects or programs that we can build, that cover both the initiatives, or both the initiatives and the seller needs, or at least help roll out these new initiatives in a way that fits with how the sellers will get value out of it, or how any account executive or right sales development rep or account manager will actually help them do their job better by playing their part in this initiative I think that makes sense.

 

Rajiv Parikh: Yeah. And so tell us a little bit. I mean, what does HackerOne do?

 

Jay Sherman: Sure. Yeah. So we basically connect our customers with a network of wide hackers to go out and find vulnerabilities security vulnerabilities before they can be exploited. So essentially, it's working with the good guys before the bad guys find the bugs.

 

Rajiv Parikh: Interesting.

 

Jay Sherman: And do bad stuff.

 

Rajiv Parikh: Okay, And so and you target fortune 500 companies, you have a lot of work, you have other clients. And they're leveraging HackerOne, to make sure that if there are any vulnerabilities in their systems, you guys find it first so that they can do whatever means necessary to patch those vulnerabilities before some outsider hacker gets there. And does it before that.

 

Jay Sherman: Yeah. And I mean, we're working with government agencies, we're working with fortune 500. We're working with small and midsize businesses. I mean, really, Every company has a security vulnerability. Especially any company with any sort of public-facing assets or applications out there. So you know, maybe more mom and pop type businesses don't have the need, but any company that has technology, it has software, of any sort. There are bugs.

 

Rajiv Parikh: I just wanted to know.

 

Jay Sherman: There are always bugs.

 

Rajiv Parikh: Yeah, absolutely. I just went to Oracle. I think that came out a couple of days ago. And by the way, we're right before the holiday season, you guys, so hopefully, everyone's ready for that. But that the government is like, you know, welcoming hackers to come in, like hack their system. Right? Part of defense and such, because there are vulnerabilities in these legacy systems that are out there. And so you guys are playing an important part, as you mentioned, with the government and these other companies to ensure that, you know, this doesn't happen.

 

Jay Sherman: Right, well, I mean, part of the idea is that with our own teams, whatever team you have, whatever you're doing, you want to get multiple eyes on it. You want to get unique perspectives and a security team, no matter how big the security team is, just isn't going to be able to look at things in the way that this kind of crowdsource network of hackers can do. And also, by the way, you know, there's traditionally a negative connotation of what hackers are we are seeing that that change and, you know, really a hacker by definition is not a criminal there. Yes, there are criminal hackers, just like there are criminal people, you know, that there are criminals, but your Average hacker is not a criminal. Your average hacker is someone who's curious. They're a tinkerer. And so we're trying to build something that gives these people a career in hacking a way to kind of explore that curiosity and Tinker and find these things that companies just are missing themselves that what they're doing today with, with pen testing and scanners and their own internal teams, whatever methods of testing they're using today, they're missing things. And when you can get more eyes on it, because it's essentially like when he when a company gets hacked, and when they're when there is a breach. There's someone from the outside that's finding something your team hasn't been able to find. So why not partner with the good guys who are outside, they have that same perspective, but they're in it for good.

 

Rajiv Parikh: So let's bring it back to your role as director of sales enablement at HackerOne. So what's your leadership style, like Jay? And how do you achieve, you know, top results with your sort?

 

Jay Sherman: So I think a couple of big things are leading with curiosity and leading with authenticity. So first, with curiosity, I'm, I always want to learn more about a problem before I just jump into developing a solution. And this, this comes about in enablement all the time, where, and this isn't specific to hacker one, I think this is everywhere, coming to enablement with, hey, we have this problem, we need to do a training. And the temptation is always there to just say, Okay, let's start building the training. But usually, when that's happening, you might be getting one slice of it one perspective on it. And also, it's like, what exactly are we training on? What's the problem here? What are we trying to solve? In some cases? Yes, it's, it's a skill gap, or a knowledge gap, where training and some combination of content and reinforcement will probably solve that need. But a lot of the time, it's actually more, there's a process issue, or we have an alignment issue. And putting training together isn't going to solve that. It’s just gonna put a bandaid on that. And then the same problem is gonna resurface in other ways, and so you're gonna, you're gonna keep seeing it. So it's not solving anything. So I really, with any sort of problem, I really want to know, get more perspectives, you know, kind of like with our hackers get more eyes on it, before I start figuring out, okay, here's how we're going to solve. And then with authenticity, I think I just, I, first off, I know, I'm not perfect, I have a lot of room for improvement, and I want to continually improve, I want to also try to do good, I want to do what's right for people, and I just want to be transparent. And so, I'm seeking feedback. I am open and honest about where I've made mistakes. And just I think that actually fits in well, with our HackerOne, we have a core set of five values that hacker wants, and two of those are leading with integrity and defaulting to disclosure. It's infused across our whole business. And I try to take that into my leadership style as well.

 

Rajiv Parikh: Great. Yeah, I think I mean, the way that I would interpret that is that you're not afraid to be vulnerable, per se. Right, which leads back to the authenticity. And getting the feedback and making sure that there is that integrity in your leadership style. And then obviously, you know, the curiosity part is great. I think the mindset of always staying curious, is just such a great way to sort of lead and then sort of have that type of purview as you sort of have a team that you're trying to manage and work with.

 

Jay Sherman: Yeah, and I think both breed trust as well. When you show that you are, you know, you're vulnerable, you're admitting where were you had fault. It helps create a culture where you have more openness. I think we see that across our leadership team. But I think it does have to start with leadership. And then, we can create a whole culture of continuous improvement, and sharing feedback and just being open and honest with each other.

 

Rajiv Parikh: Right, so in your opinion, what is the scope of sales enablement?

 

Jay Sherman: Well, you know, I think it depends on the organization and where enablement fits in the organization. But probably more importantly depends on who is running sales enablement, and just the sales enablement team. You know, I think if sales enablement can be in L & D, and there it's probably more focused on training. It might be under sales operations where.

 

Rajiv Parikh: L & D by the way, learning and development.

 

Jay Sherman: Sorry, yeah, learning and development or HR. Under sales operations, it may be more process tools, systems. Under Product Marketing, it's probably going to be more about content, And where it sits in HackerOne, I report directly to the head of sales. And I think being part of the sales organization and being a member of the sales leadership team is where enablement can really do all of those things and more and, as I was saying earlier, kind of be that bridge between strategy and execution. And that's where you can really deliver a lot of value out of sales enablement.

 

Rajiv Parikh: So based on your different audiences, you are sort of evaluating that and making sure that you're enabling the right type of content so that they are successful in what they need to do today.

 

Jay Sherman: Yeah, it may be content, and if it's content that is, what content do we need, and develop and working with across the organization and maybe working with Product Marketing, maybe working with customer success, maybe working with our security team, whoever. To build the right content that will actually help enable whatever sort of behavior or skill we're trying to develop.

 

Rajiv Parikh: Are there other assets you see besides content? That's effective?

 

Jay Sherman: Yeah, I mean, a big one that's been effective for us is just calls like actual customer calls. So, you know, I came on board about a year ago, and pretty quickly, you know, and when we onboard, folks, we, you know, they go through a whole set of training, they have resources, there's activities, exercises, we do role plays, all that sort of stuff. But it's still missing, like, well, what are actual customers saying what actually happens? On a phone call? Where the security buyer and so there's just nothing that does that better than actually listening to call? So of course, you can shadow reps on calls. But that's not totally scalable. And sometimes it's a little funky having someone on a call, just sitting there. So having call recordings and being able to share that library with the team is something that we've kind of just rolled this out but had a lot of success with it.

 

Rajiv Parikh: That's great. Why do you think sales enablement isn't an important investment for companies?

 

Jay Sherman: So I think a few reasons, I think it's about getting a return on sales investment. It's about recruiting and retention. And then it's also about having a longer-term view from within the sales team. So for those, I mean, the return on sales investment, like, cost of sales is high for most companies, right? One of the highest costs, especially in SAS, and with sales enablement, you can help ensure that you are accelerating ramp time. So getting new hires up to speed faster, boosting productivity, adopting new initiatives, driving change management, that's something sales enablement can help drive and help you get more out of the investment, putting in sales. Recruiting and retention, I mean, people coming into a new company, they want to know their support, right? They want to any can't leave that off to the managers, managers play a critical role in onboarding, but they have a lot, they have their currency, there's, there's a lot, especially a frontline manager there is so much on their plates, and so you're gonna get out of that inconsistency, you know, how we train on our methodology or messaging, or you know, all of this stuff is going to be a little different manager to manager, so you get that inconsistency. And then there's just the stress for the managers, and for the new hires who are kind of desperate.

 

Rajiv Parikh: So take that off their plate.

 

Jay Sherman: Take that off their plate, and so for recruiting purposes, when someone who's evaluating companies sees that there's a strong enablement program in place, and part of that is sales, onboarding, they know they're coming into an environment where they'll be supported, and they can be successful.

 

Rajiv Parikh: Absolutely.

 

Jay Sherman: And then on the retention side, of course, once you're in, people are looking for career path they want to develop. And so it's the same thing, it's, it's working with the managers to build that career path. And, you know, whatever it that means from a training content and coaching perspective, but kind of putting that structure in place to allow people to grow. And then the last piece is just having that kind of long-term view from within the sales team. Of course, you know, sales leadership, especially the head of sales, should be taking that long-term view. But sellers and frontline managers, it's really day to day, month to month, quarter to quarter you know, yeah, you're probably driving for building up your pipeline thinking ahead, but that's about as much as you're doing to think past what's happening this quarter. And sales leaders themselves, they're getting bogged down into those day to day, quarter by quarter details as well. So when you have sales enablement as part of the sales team, you have someone who's always kind of working side by side with sales, but is able to kind of take a step aside and be thinking about, well, how are we going to keep being successful next quarter, next year, and so on.

 

Rajiv Parikh: Got it. And so, as director of sales enablement at HackerOne, how did you sort of approach the initiative? from the ground up? How did you build it? What was your vision? What was your strategy? What advice can you give folks out there that are in sales enablement, that are trying to figure out the right combination here at what do you do that you saw that was successful? What are any learnings that you can share with us? That didn't work for you? Or that you were successful with?

 

Jay Sherman: Yeah, so I think. So I started at HackerOne about 14 months ago and was the first sales name and hire, so building sales enablement from the ground up. You know, there were certainly some pieces in place that sales leadership had developed. And my current boss had put it in place, but it just wasn't scalable or sustainable for the head of sales to be doing sales onboarding and all that stuff. So anyway, so I came in to build things from the ground up and certainly had ideas coming in. But I came in and just put all those in, I had to have ideas to get the job in the first place, but I came in and immediately put all those ideas in the background.

 

Rajiv Parikh: And those ideas came from the previous experience you were at Okta before HackerOne.

 

Jay Sherman: Was that Okta before? Yes. And so certainly had some ideas about some things we'd done at Okta to bring in to build the foundations for sales enablement at HackerOne. And also, just in going through the interview process and learning about what was going on at HackerOne, what the needs were developed some early ideas about what could work, right, but came in and tried to forget about all that, at least initially. So it was all about leading with curiosity. So and for me, I kind of think about it as I approached it with a sales mentality, I went through discovery, and then would do solution mapping. And then we would get to delivery and execution. But for my internal sales enablement discovery, I made it a goal to talk to every single person on the sales team and a number of other cross-functional folks within the first four to six weeks.

 

Rajiv Parikh: So absolutely discovery.

 

Jay Sherman: Yeah.

 

Rajiv Parikh: Learning what's happening

 

Jay Sherman: Learning what's going on.

On nation look like.

Exactly. And you know, when you think about building a plan, step data that goes into the plan. And in this case, the best data was just information in people's heads. So the only way to really get that was, was having conversations, but I wanted to be structured. So I put together a whole standardized set of questions to cover with all the individual contributors, and then a whole set of questions to cover with sales managers, and sales leaders. And there was a kind of quantitative rating questions. Then more qualitative, open-ended questions across about eight different areas and went through all of that with everyone ended up collecting 112 pages of notes. And so then it became analysis time, dug through all of that, and then just pulled out insights of, Okay, here's what's working, here's what's not working in all these areas. And then also just kind of here are some overarching themes and pain points. And also, you know, where we're doing well, and actually, from there, it became pretty easy to start putting not shouldn't say, easy, the harder part was doing all those interviews, going through all of that information, once I kind of had that all put together, a lot of the solutions just kind of became very clear, and so built out a whole plan, you know, with OKRs objectives, key results for the first year, along with a roadmap for all the tasks and projects that would roll up to address those OKRs. And then it was just execution and just kind of heads down. And you know, of course, you have to adjust things change, new initiatives, new challenges, periodically reassess. But for the most part, I've been able to go through 2019. With that plan, it's probably stayed about 80% true to plan.

 

Rajiv Parikh: That's great. And how long did it take you from your onboarding to get to a sales enablement strategy that you were satisfied with?

 

Jay Sherman: Two months?

 

Rajiv Parikh: Two months? That's not long.

 

Jay Sherman: So yeah, I wanted to show that I was bringing in value as soon as possible and that's part of why I was trying to get all those interviews done within the first four to six weeks. And then I gave myself two to three weeks to turn it around. Once I had the plan put together, you know, kind of did another round with sales leaders, got their approval, feedback, made adjustments. And then, once I kind of had it all down, presented to the whole sales team what we were doing with sales enablement in 2019, because it was important to me to show that I didn't just come in here and talk to everyone. Yeah. Here's what I'm doing about.

 

Rajiv Parikh: Sure, absolutely. You need some action to the words. That's fantastic. Thank you for sharing that. Jay, can you share any tips for organizations on how to really boost sales? Productivity?

 

Jay Sherman: Yeah, well, I think one of the first ones that jump to mind is something I mentioned a little bit earlier around call recordings and conversation intelligence. There's some great solutions out there. But so we put a solution in place for conversation intelligence just a couple of months ago and have started getting value out of it right away. So what it does, captures all the recordings. Right now, we started with just a couple of teams but captures the recordings, or the conversations that these teams are having individual sellers are then using these calls, or the recordings to analyze for self-improvement share with their managers for coaching opportunities, review calls for preparation for follow up calls, we're able to better focus on the conversation itself, rather than just taking notes seriously.

 

Rajiv Parikh: Sure, you're focused on the moment.

 

Jay Sherman: Exactly, yeah, you can actually listen to what people are saying. And then for the managers, I mean, that they're able to work together better with reps, if a call happened to the manager wasn't able to join, they can still listen to that later. Or they can say, Hey, you know, this happened, or this question came up, this objection came up, how would you have addressed this, right. And then there's also stuff, just sharing across team sharing with product or product marketing, that, hey, this is what customers are actually seeing. You get a lot more of that context to share with the rest of the company. And then, of course, for onboarding purposes, or just for development across the team for continuous learning, having this whole library of calls to listen to where you're actually hearing how these conversations go, and what people are saying you get best practices out of that, that one's been huge.

 

Rajiv Parikh: And so but in terms of those calls, and I love that, that's great. Are you providing scripts? Or are these calls a combination of templates? And, you know, based on what's being said, They're adjusting the conversation? Are there decks that you're providing? How is that work?

 

Jay Sherman: Yeah, you know, it's really a combination, we don't necessarily have scripts, Um, we have, first off, we have a sales methodology. And that really covers how we sell how we approach discovery, leading by learning about all these different components about what's happening with the business today. And, you know, it's, I take this approach with sales enablement, just about everything is learning what's going on first, and then kind of putting a solution in place. So we have that framework for how we run those calls. So we do a lot of training to kind of develop mastery in that framework. And then you know, we serve, we have a discovery guide, and we have questions we recommend. But part of having those sales methodologies is about active listening. So, you know, we kind of send reps in with questions they can ask, but it shouldn't just be a list of questions, listening for kind of key nuggets that you're getting out of the answers, and then digging in and getting those second-level questions. That's where you get into some real pain. Real objectives for the business. So it's more teaching the skill of discovery, then it's like, here's exactly what you need to say. But you can get a lot better at that a lot faster. When you hear more of what customers are actually saying, you know, without having to, of course, eventually, you have to just go do it. But I think you can ramp up your learning faster, when you can hear other examples of people having those conversations, what buyers are saying and where sellers are doing things well.

 

Rajiv Parikh: Great, awesome. What are some of your top sales enablement initiatives?

 

Jay Sherman: Well, the big one for me in 2020 is hiring. I'm building out the team. So I'm growing from a team of one to a team of three, which is very exciting. I think a great proof of success in the first 14 months. So I'm right now hiring for sales, onboarding manager and their big initiative is going to be evolving our sales onboarding. And then in about four or five months, I'll start looking for a sales Content Manager, which will be, you know, managing content, but also developing content. And so a big initiative there is going to be developing playbooks that support all of our bigger company or sales initiatives. So I think that's one big way we're going to tie sales enablement or use sales enablement to support and roll out these bigger company initiatives to the team. So how do you actually run this initiative or run this play with, you know, laying out all these different scenarios, all that stuff.

 

Rajiv Parikh: So anybody who's watching now can Apply for these job.

 

Jay Sherman: The sales onboarding manager role is open now. Yes, I am definitely looking for that one, though. The content role will be open in about four months.

 

Rajiv Parikh: Okay. Perfect, and so and you know, in your opinion, where do you see HackerOne in the next five years, the next three to five years?

 

Jay Sherman: I think it'll be interesting. You know, we're creating a category right now. And I think, you know, we've got a lot of innovative companies working with us today for thinking companies that have opened up to this concept of inviting this network of white hat hackers and to find and submit vulnerabilities, I think that will continue to build value there. And more and more companies will see that value and hacker powered security will become a core component of the security stack. And hackers will get more away from that, you know, mentality of, you know, hackers are criminals to Oh, hackers are creatives. They're tinkerers. And, of course, there are criminals out there. But they're criminals, just like any other type of criminal.

 

Rajiv Parikh: A lot of bad actors out there.

 

Jay Sherman: Yeah, they're just criminals who have a certain set of skills, but most hackers are good people. And they have a lot of value to bring to these companies.

 

Rajiv Parikh: Great. Thank you so much for that. That's all the questions I have. Jay, is there anything else you'd like to share with us?

 

Jay Sherman: No, thank you very much for having me here. The last thing I'll say is definitely send any sales onboarding manager candidates my way.

 

Rajiv Parikh: There you go. Thanks a lot for your time. Appreciate it.

 

Jay Sherman: Thank you.