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Scaling Your Onboarding Efforts

| 48 min read


Misha McPherson: I’m so excited to be here today. Not only is this one of my favorite topics to talk about, but we have an amazing panel of people who’ve done it. They’ve done it successfully, again and again. I think that scaling is such an interesting topic because it is so risky. There are great rewards at the end, and it’s really exciting, but it’s so risky to scale your sales team. One of the things you want to make sure of is that you’re actually getting your return on your investment on all of those extra butts in seats. You’re hiring these people – are they the right people? And are you ramping them correctly? Often, when you try to scale quickly, your ramping slows down. How do you prevent that? That’s really important. Often as you’re scaling, your sales process is changing. It’s very common that you start going from – you did SMB and you did mid-market, now you want to go enterprise, and enterprise is a totally different game. And it’s really important that as you’re doing this, that you’re doing it correctly and that you’re doing it in a way that is preventing a lot of hurdles. There are so many different hurdles.

The people we have here today – we have people who have done it. They’ve done it again and again, successfully. So I want you as we go through – I’ve got some questions but we’re actually going to leave a lot of room for your questions as well, because we want to make sure that all of you – you woke up, you got here, potentially after a concert at 9 a.m. – so we want to make sure if you have questions that we’ve got answers for you. So we’re going to kick it off by doing just quick little introductions. We’re going to do name and where you’re currently at, but then what I actually want to start with is one that you’re really – just one, it’s hard, you’re gonna have a lot – but one thing that you’re really proud of as you’ve scaled up sales. What’s one thing that you’ve done that you love talking about? Start with you.

Marcela Piñeros: Alright. My name is Marcela Piñeros, and I lead the design group for sales excellence at New Relic. And it is hard to think of one thing, but probably I would say that what I’m most proud of right now is being able to scale the sales team at New Relic and being able to maintain and retain the culture and the spirit of the company when you’re scaling. So one of the things that will often happen is that we’ll just go straight down to business, and then we end up stripping anything that’s truly cultural in the content. You hear it from success stories from the field, whether it’s a new hire that came through, did a workshop with us, and then walked out and two quarters later lands a seven-figure deal and sends an email saying, “this was thanks to you” or senior leaders that will point to our programs and say, “that has a direct impact on retention, on productivity, and overall annually for our market”. So that’s really rewarding.

MM: Fantastic.

Steve Maxwell: I’m Steve Maxwell and I lead enablement for Medallia. The one thing that I thought of when we decided to do introductions here is a little bit of validation. So when I led enablement at ServiceNow, I was the first enablement person at ServiceNow and look at what it’s become. And the recognition we got for how we built and scaled on onboarding program ultimately won the SiriusDecision’s award for Onboarding Program of the Year. So, validation of that – what we’re doing works, but also recognition across the industry that it’s best in class.

Courtney Skay: I’m Courtney Skay. I lead enablement at Okta, and we’ve had over 600 people go through our boot camp in the last 4 years, which is pretty much half the company. And I think the thing that stands out for me is time and time again, especially as we’ve started to hire a lot more experienced sales individuals – they come to us after boot camp and say, “that was the most impactful boot camp I’ve ever been through and I’ve been through several at much larger companies who have a lot more resources.” So, I think that’s a testament to what you can do.

David Bloom: I’m David Bloom, I’m the CEO and Founder of LevelJump. I am actually most proud of being selected on a panel with what these people have accomplished.

CS: Thanks for coming.

DB: Anyways, thanks, guys. Thanks for having me. In reality, thinking also from a validation perspective as per Steve, I used to work at Salesforce and that’s where I really learned about ramping. It’s funny – you think of Salesforce, the little software company that John mentioned. It’s amazing, even with how big they are how seriously ramp is taken. I remember being there 60 days and then I was considered a veteran, onboarded or not, and it was kind of like, “okay, guess what, the next cohort, you’re in charge” and I’m like, “what do you mean? I don’t even know what I’m doing yet.” That was actually a big inspiration for leaving and starting this company LevelJump – to do exactly that. So I’m looking forward to sharing some insights with everybody here.

MM: I have to say, you stole one of my favorite things. So when I was at Responses, I often had people go through my boot camp they were like, “I came from Salesforce, I came from Oracle, this was so much better”, and deep down you’re like, “oh yeah, yeah it is”. Perfect, so the first question – we’re going to start with you, Marcela.

MP: Okay.

MM: We’re going to talk about common challenges you face when you’re scaling sales. And I know we’re talking specifically about onboarding, but if you want to expand out a little bit beyond that as well.

MP: Sure. Okay.

MM: What are the hurdles?

MP: I sat down and started to write a list of all the challenges that you can face when you’re onboarding. I stopped when I hit 20 and I scared myself. I decided to pare back and I thought, “okay, let’s narrow it down to three”. So, I looked at the three that I had most frequently seen, whether it’s onboarding startups or the work that I’ve done onboarding sales programs for Fortune 500. I found that there are three things that are very common. That said, I said my list is long so if I don’t mention one that you’re stumbling against or you’re running into, come up to me – I’m happy to talk about it later.

So, the three would be this. One, boiling the ocean. Feeling that you have to boil the ocean. The other is getting misaligned with marketing, with the product, and with the field. And the last would be waiting way too long to train your first-line sales managers, thinking of that kind of as an afterthought. Going to the first one, with boiling the ocean – especially as a company is growing, as a function is growing, what you’re going to see is that there are more teams that are being built out that are demanding – very loudly – role-specific training. Right? And you feel like you have to cater to the entire company, to all the different roles. So my advice is, focus on the 80/20 rule. Focus on the 80% that applies to everyone and if you’re struggling to figure out what that common factor is, consider the customer. The customer is one thing we all have in common, regardless of your role – whether you are customer success or engineering – the customer is one thing we all share, so focus on training people around how to support the customer. What are the use cases, the personas? What are the challenges? How do we support that customer better than the other guy?

MM: Before we go on, how large is your team today?

MP: The sales excellence team?

MM: Mmhmm.

MP: So – we’re hiring, by the way, so come to me if you’re interested – but we’re I think at 17, 18 globally.

MM: I’m just curious, how many of you are facing the problem of trying to boil the ocean? Good. How many of you are armies of one or two? Right. So I can actually see that this is one of the biggest problems we start facing. The less people you have in your sales enablement, your sales excellence, your sales readiness team, the more they want you to just fix everything.

MP: Yes.

MM: So I think this is a really key point and something to talk amongst yourselves about and then also come talk to us afterward as well.

MP: You want to be strategic. You want to think through where you’re going to put your resources. I’m not saying to ignore the craft programs, but you can crowdsource a lot of that work. So you can partner with the leaders and the superstars in those teams to help build out, what would an onboarding plan look like? And then work on making that more of an official plan that you can streamline but you’re not necessarily having to govern to because there just aren’t enough hours in the day to do that. So boiling the ocean, it’s an obstacle, it’s a trap we fall into. There are ways around it.

The second one, which is getting misaligned with marketing, with product, and with the field. So, when things move fast, the faster they go the harder it is to stay connected with all these moving parts. By letting that gap grow, we’re actually doing ourselves a disservice for two reasons. One is that it’s in your best interest for sales enablement to be at the table with the product team when they’re deciding when the next release is going to be, with the marketing team when they’re working on messaging and when they’re figuring out what’s going on, with the sales team when you’re trying to understand, am I enabling to what the customer’s actually going to benefit from – right? So you need to make sure that those teams are aligned, and I encourage you to be maniacal and disciplined and really passionate about building those relationships and having frequent touch points with those teams. That cross-functional collaboration is critical to onboarding – whether it’s sales or anything else in the company. But prioritize marketing, product, and actually a feedback loop from the field.

And then the last one is waiting too long to enable your first-line managers. We all do this, and it’s something that comes back to bite us over and over and over again because at the end of the day your first-line managers are your amplifiers to the field. They are the ones that are going to be able to help you roll out that new process and avoid preventable mistakes. And they’re the ones that are going to help you ensure that the feedback that’s been going to the field is something that’s productive. There’s nothing worse – and I think many of you may have experienced this – than doing an enablement program, an onboarding program, and having someone say, “oh, my manager told me not to do it that way”. And you’re like, “oh no”. You need the managers to work for you and to help you be boots on the ground. It’s really common for us to assume that managers know what good looks like, that they put on the manager hat so now they must be able to know how to coach and how to facilitate. They don’t. Many of them were star performers we promoted, and they have no idea, so we need to take the action of providing them with the resources, giving them manager toolkits, helping them help us avoid skill-fade with the team long after onboarding has happened.

MM: On that topic, I think this is one of those things it’s really easy to talk about – it’s really easy to talk about and I think deep down inside probably every single one of us knows it – the hard thing is doing it. Actually doing it is really difficult. So, again, just huge, huge applause to the team who brought everybody, all of the different panelists, here together. Work with everybody to figure out how everybody else is doing that. And come up to us as well, because it is such a key thing.

Let’s go to you, Steve. And it’s a very similar topic. Who are some of the key players you should be engaging with in the organization?

SM: The point was all these pitfalls and recognizing that. You know, unfortunately or fortunately I’d seen that movie many times before, especially as it relates to first-line sales managers. So the very first thing I did when I joined the enablement team at Medallia was front-line sales management training, and getting them connected to the vision of what we were going to build as an enablement program. If we don’t do that, it’s virtually impossible to scale, because if we’re talking about scale here, we’re a small team. Most people with the hands raised are members of small teams trying to enable large programs and larger organizations – you have to be able to scale. You can’t do things the old-fashioned way: “Oh, well I’m going to run a training class and people will show up and then the skills will be there and the managers will coach.” I’ll guarantee you that the first priority of a sales manager is not to coach their team. It should be, but it isn’t. It’s about the deals because that’s what they’re measured against. Right? So it’s always challenging to make sure that the leaders are there. So that was the very first thing that we did.

But we – in order to really scale – partnered with IT, other technology vendors. Because there’s so much great technology out there, you have to be able to leverage it in a way that helps you scale. So, IT, subject matter experts, of course marketing, so we’ve now automated our onboarding process. From the moment that new hire signs their offer, we know about it: when they’re going to start, as soon as access is live they get pushed into our 12-week weekly – what we call rapid deployment training. And those things are gated and there are assessments associated with each of these gates. The thing that we’re most proud of is the last thing we’ve just done, which is to then close the loop with the manager.

So we’ve now instituted a process whereby the managers get triggered for their weekly – because part of the management training we had done before was that you have to have a separate coaching conversation than a one-on-one because one-on-one’s become deal reviews and what’s happening in the business. Separate that conversation from the coaching conversation. Now in the coaching conversation, we have what we call a weekly reflection. So the things that are happening – if you’re in week one or week two or week ten, the manager gets triggered that your person who’s onboarding, in week ten these are the things that they need to know this week. In your weekly reflection, you need to validate whether that skill is present or there’s still a gap or they need to go back. Then we’re able to not have to try to follow up on those people.

We’ve onboarded in the sales ecosystem as Medellia probably 350 people in the last year because we do all sales roles, whether they’re SDR or inside sales or strategic accounts or account management or pre-sales – all of them. And each one has his own or her own needs. You can’t follow up on that yourself, and if you don’t connect the dots with all of those partners then what happens is they just assume that we’re doing it. And it’s physically impossible for us to do. Plus, they have to have – to take ownership of their team. That’s where enablement crosses a boundary into management and we’re not their boss. They have to take some responsibility. So those partnerships are critical.

MM: So, quick question for you guys. How many of you have sales managers – or feel like the majority of your sales managers are resistant to the work that you’re doing? We have some. How many of you suspect they really don’t know what you actually do? Any? Yeah, I see some hands.

DB: Hey Misha, before we do this, as we trash sales managers – any sales managers in the room?

MM: No, no, no.

DB: No, but seriously, don’t be embarrassed, you shouldn’t be. But are there any – seriously, anyone in sales management in the room? In the back, we’ve got one. There are some hands – how about giving a round of applause for sales managers being here at this conference. Seriously, you deserve to be recognized because I think this is part of where you’re going with this discussion. Sales managers need visibility into these kinds of conversations. We’re not here to make them look bad. It’s actually the opposite, we want to turn them into superheroes. We’re like – any James Bond fans? We’re like their Que. Look at all these gadgets we have to help you hit your objectives. So, awesome for sales managers here.

MM: Well, in a weird way I’d also like to say that we also have to earn the right. We actually have to earn the right. We actually have to move the needle on revenue, we have to show that we actually know as much – we should know as much – about sales as they do. On top of that, we should know as much about marketing as our head of marketing as well, right? Sales enablement is an amazing role. I love this job, I’ve been doing it for a long time. It’s great because you never stop learning. But we have to earn the right. And then how many of you have sales managers who are your partners in crime? Great. So there’s a whole range. If you are somebody who doesn’t have the ear of the salespeople, go find those people who do and find out what they’re doing. Thank you so much.

David, we’re going to talk about metrics. Metrics is a good one. So how do you actually know that your onboarding program is scaling correctly and that you are actually moving the needle?

DB: Yes. We obsess about this question. This is the thing we talk about with so many. Curious, just in the crowd, how many are venture-backed companies? Okay, and then how many are publicly-traded companies because you think about scale? Okay, so when you think about the scaling of onboarding and the metrics if you’re venture-backed and you just got a check for, whatever it is, $50 million, that’s typically to scale your sales team and start going faster. If you’re publicly traded, you have a board that also wants to see growth, and scaling your onboarding typically comes with scaling your sales.

So when it comes to metrics, when we speak to customers, we get amazed often at how many metrics are not being tracked. I think in terms of being aligned to sales management and other executives it’s understanding the metrics that they’re eventually or currently being judged on and then being completely aligned to that. And what I mean by that – and I love the example that was brought up – there’s nothing worse than running a boot camp or an enablement program where the seller gets back to the business and the sales manager says, “Welcome back. Now let me tell you about how it works in the real world.” Right? I say it tongue-in-cheek but everyone knows that happens right, like, “Yeah, I get it. You went to boot camp and you rah-rahed and you –”

MP: You checked the box.

DB: What’s that?

MP: Check the box.

DB: Yeah, like, “You did it. Congrats.” It was like your Frosh week sort of thing. Like, “okay, you finished drinking, you finished all this stuff, you got all the swag, now come get to work and let me tell you how we work around here.” And I think to understand what’s on the mind of the sales leaders – and we’ve also touched on this as well – sales leaders don’t have the time. They’re kind of like, they look at you and say, “Okay, onboard my reps. Because I’ve got to hit quota and run the deals and deal reviews.” So they think it’s your responsibility, but you’ve got this short amount of real estate and time to do it, so what happens after that? And the metrics they’re thinking about is, as a sales leader, is my rep ramping fast enough? Because ultimately, they’re going to sit in a board meeting, whether your publicly traded or you’re a high-growth venture business, they’re going to have board meetings where the questions are always going to become, “How are our new reps doing?” And this is where it comes to the metrics, how do you answer that.

My first answer you’re not going to love because I obviously say it depends on your business – and it goes by different roles, so I love this idea of personalized by role. But let’s just take sort of the typical AE. I think the best acronym to remember, we internally call it TTF, Time To First. And it’s Time To First [Blank], you choose what that is. So, as an example, the outcome we’re all looking for and that every sales leader wants is – some know this, some don’t, which actually is the first frightening piece – the benchmark. How long does it currently take to ramp new people? And what does ramp mean? Is it time to first deal, is it time to first pipe deal – and that depends on your business.

And, you know – there’s a lot of stats. Is everyone familiar with the bridge group, by the way? If you’re not, they have amazing statistics, and what they do is they actually share the benchmarks of what your metrics should be based on ACV size. It’s common sense in a lot of ways, but they’ve benchmarked it against 400 companies that they’ve interviewed. If you’re a smaller ACV, ramp time should be faster, and if you’re a longer deal cycle, whatever it is, that should take longer. But the key metrics in each of those buckets you want to measure for BDR could be time to first meeting booked, it could be time to first opportunity found, time to first lead converted, however you’re managing your business to manage time to first. Time to first deal, whatever you want – time to first upsell if it’s CSM, but time to first is not the only one. That’s the leading indicator in a lot of ways. What about time to second, time to third, time to fourth, and tracking that over time and having that benchmarked.

That’s the key thing if you put an investor hat on. So, take yourself out of the role, imagine you were an investor – you made all your money on whatever stock options you have at where you’re working because your enablement was so good and now you’re an investor in a business and they’re sitting there saying, “Okay, you’re an investor and you know a little bit about enablement. How was your onboarding?” What would that investor want to see? They’re not going to care about the exercise you ran – “yeah, and then we had them break into groups and they roleplayed and we did a case study and they presented to each other.” No investor cares about that. They want to know before you started, how long did it take the AE, BDR, CSM to get to that first X, the second X, and how much faster are they getting to it now since you’ve put that enablement program in place. I think those are the types of metrics you want to obsess about. Think of it if you were an investor, as an enablement professional, and you were being looked at. “Hey, we’re going to invest in this company, how do you think their onboarding is?” What metrics – and I think that’s a great starting point.

MM: Yeah, and I think one of the key things is thinking like an investor. I think us having business conversations, real business conversations, is going to do a ton to actually move how we are perceived within our teams. I think that’s fantastic. One thing I would also suggest is that if you’re working with enterprise, you sometimes have to cut people before they hit their full ramp. Enterprise ramp might take you nine months. If you have the wrong person in the role for nine months, that is a lot that you are paying in terms of everything. So I think it’s really important that as we look at scaling our onboarding program we actually have some indicators that we’re going in the right direction or we’re going in the wrong direction. This is coachable, this is not coachable. Mistakes happen in hiring, especially as you’re scaling because you’re hiring profile is going to change.

So we have one last question and then we’re going to go to everyone. So finally, Courtney. One of the big questions – and it’s a really hard question – is if you have a technical sale, one of the questions that we always have to answer is how technical do you make your AEs? I think you’re a really good example because you’ve scaled out the company so far. Also, how does that change, going from a technical sales person to actually having a team?

CS: I think focusing on technical AEs specifically, we could kind of slice and dice this a million different ways per role. I think the big thing is don’t be afraid of changing it over time. How many people have technical sales here? Yeah. It’s hard, it’s not easy. Going back to what Steve said earlier, you’re going to make a lot of best friends in the company and the best friends that you should make for this specifically is your product marketing team. They’re super critical when building out the marketing. We have a great product marketing team who is really supportive. I actually came from product marketing so maybe that helped – they’re super supportive of enablement and our sales organization. In the beginning, it was very much, “so we’re going to train the team on product”, and it was a lot of focus on product and really not a lot of focus on sales skills whatsoever. We were building an industry, we were educating the market, and it really required all hands on deck to get there and it was a lot of focus. We weren’t even sure what all of our use cases were. Over time, that did evolve. Somewhere in the middle, we started to train our sales organization with the selling methodology, and “command of the message” is what we happen to use internally. And it is married a little bit to the two – the technical sale as well as sales skills.

We could have stopped there, but that wasn’t going to work, just to do a one-time training. So, what we’ve done is actually really incorporate the two as part of our onboarding program. As part of boot camp, we’ve now kind of shifted so it’s less about product and more about the place and really the value. So our sales team, now that they are a lot more up-leveled and companies know our industry, it’s been easier to do that because we can up-level our sales team so they’re more about selling value, having those higher level conversations with the CIO, still giving them some sales skills but also giving them that information. Then at the same time, we’ve been able to hire more technical resources to take on a lot more of those technical conversations, and we train them in a very different way. I won’t go into details there unless people are interested.

MM: But come afterward and ask, because they are really good details. When I was at MixMetal, the first day we would make sales reps create a website. It was because when I first got there, we had a handful of sales reps and we didn’t have a lot of people. And then that changes over time. One of my favorite things now is you focus a lot on the buyer, you focus a lot on the messaging, you teach product and all the technical stuff later so that they’re actually talking about the things they should be talking about. So now we’re going to open up the floor. We have a microphone moving around – who’s got some questions and some problems to solve?

Emcee: If you have a question, raise your hand and I’ll go around and try to remember the order in which you guys raise your hands. But just while I’m walking around, a real quick question for you, Misha. You used a phrase, which was that you have to earn your right. Could you just real quick think of some specific things that you have seen or maybe have done in onboarding or enablement programs that have earned you the right to participate?

MM: Yeah. Talk about revenue, like actually talk – speak the same language. Speak the exact same language. And that language changes if you’re talking to sales, if you’re talking to marketing, or if you’re talking to the COO. So with revenue, with CROs, CSOs, what I’m talking about is revenue going up or hitches that we’re hitting. With COOs I prefer to talk about costs going down because we really should be doing both at the same time. We should be increasing revenue and decreasing costs. But, know your audience. Especially when you’re talking to executives, they don’t have time for your novel of what snack you gave your sales team during their boot camp. They need to know the bullet points of specifically what the problem is that we’re solving for, how are you addressing it.

SM: The other thing that I would add to that is to ask your leader – whoever your leader is – for you to be measured on the sales leaders measurements.

MM: Oh, yeah.

SM: If they’re measured on new logos and revenue growth and all these kind of metrics, ask for at least a portion of your compensation to be measured on the same things, because then they know you’re in the same boat rowing in the same direction.

MM: And that’s something Raj and I have talked about a bunch. How many of you feel like you’re getting paid enough? Oh, come on. You guys – really, you all are just making millions? Amazing. Sales enablement doesn’t get paid enough. And the reason why is because, for the longest time, we have been judged on smile sheets. Did people like the class? That’s not enough. We actually have to move the needle, we need to make salespeople more effective. And we need to take the risk. And to your point, we should very much be comped in the same way. If the sales team is performing, we should get comped for that. And if they’re not, we haven’t done it. That’s great.

Audience 1: Okay, so in response to David’s mention of metrics, there’s a great panel at 10 a.m. on measuring sales enablement success. My question is actually for Steve. So you said you had a 12-week fully-automated onboarding, which I think is a beautiful thing. My question is, if it’s fully automated, what percentage of the people go all the way through before they’re just in full sales mode? What percentage of the people drop off during that automated onboarding program? I can envision how it works, I know the systems – how many people go all the way through? What happens if they don’t? And how do you prove if people do better when they do go through – because that can be hard. I’m curious how the full automation works. I feel like there’s a mix somewhere in there and there is a sales boot camp kind of along the way.

SM: Yep. And we do that. That’s a good question. And there is, in those 12 weeks, a boot camp that they attend. And as you might imagine, once they attend boot camp things tend to drop off a little bit. With the weekly reflections that we’ve now started, we’re trying to get more outcome-based to it, so that it’s almost okay if they drop off if certain conditions are met because there’s an assessment at the end of 12 weeks that they have to be able to still deliver against. But, it’s hard. I mean, I have partnerships with sales leadership and it’s still not mandatory, which is a battle we all have to fight. How far do you push to make things mandatory? Again, they don’t work for us, so we make recommendations and that’s where the partnerships really have developed, because you can try to demonstrate or prove or justify that they need to go through all 12 weeks. So it’s a challenge. I don’t know the percentage, it’s pretty high, probably 70% go through all the way.

MP: So, one thing that I will say – we actually tied participation in our onboarding to MBOs for the AEs. So we kick off our product and our sales knowledge in parallel. Weeks one and two, we require people to stay in the field. They don’t come to – we don’t call it boot camp, we call it Activate – they don’t come to immersion until their third week or more in the role.

SM: Same with us.

MP: Their first two weeks in the role, they’re spending their time putting together product knowledge matrixes and getting buyer persona exercises together and they’re going through processes, they’re doing shadowing, they’re completing a series of videos that I want to streamline and make lighter. But anyway, I digress. At the end of every week, they have checkpoints with their managers. And their managers are responsible for running roleplays with them and assessing them against those roleplays. Their achievement in those points gives them credit towards their MBO, which is tied to their comp. So their variable comp – they will get paid on how well they are doing, meeting these milestones and these gates. When they come to immersion, at the end of immersion we’re requiring all of our AEs to do demos and they have to be very technical. So we acknowledge, especially in our space, which is a digital intelligence and monitoring space, we acknowledge that you can’t just have a top-down conversation, you need to be able to do both. You need to be able to speak with practitioners and you also need to be able to speak to CEOs. So we’re training people to be able to do both. And there is a lot of tracking along the way.

Audience 2: To add on to that, I would love to hear from all of you how your onboarding structure scaled. So, some of you may have been closer to the startup and now you are a larger organization – how has your program structure scaled, expanded, changed over time?

Emcee: Thank you, great question.

MM: So, I’ll take a quick stab, because I’ve done this a few times at this point. It changes, and it depends on when you step in. So if you step in really early on, one of the things that’s important is that you grow your program at the same time that your org is growing as well. And that means including growing out your own team. Too often I see at companies that start with a sales enablement army of one, and then they hire 500 people, and they’re still a sales enablement team of one. We have to ask for budget, we have to grow the team that’s appropriate for our company and that has to scale out. One of the things that I typically change over time is that you start off with your classroom. But my favorite thing is to see if as you scale, you begin bringing it through the entire ramp. So what I mean by that is if you have a nine-month ramp for your enterprise sales rep, you should have a nine-month ramp onboarding program – not classroom, not hours of their time, but you should be following along and making sure that as they’re getting deeper into the sale, they’re also getting that additionally support. That’s the shortest answer I can give.

SM: That’s what we did. We started with a classroom, then we added more modules to build out the 12-week cycle, and then once it was getting to a point where we were going to have a massive hiring boom, I hired a person dedicated to onboarding and that’s all they did.

CS: I feel like we were doing catch-up for a while. We did our hiring boom and then we hired, which I feel like is also a very, very common scenario. So for a while, it was just kind of one boot camp quarterly, and I was actually still in a product marketing role, so it wasn’t even my full-time job at the time. And then we eventually hired to start building that out. We had somebody own onboarding, that was the first hire for the team. It really was like, “okay, we’re going to start running it more frequently, we’re going to start building out some online modules pre-work so when they come to boot camp they can be more productive versus teaching them the basics”. Getting that interaction, getting that experience at headquarters was a lot more valuable. And over time it’s like, “how do we start to change it?” We’re going through another evolution at the moment of really breaking it down by role and really expanding that to get more customized.

DB: I mean, to build on this, I think it’s important as you’re scaling to think of – again, I’ll say the investor hat and even the marketing hat – people AB test campaigns. What worked better? And you need to be taking a similar approach to an onboarding program because the onboarding program that wasn’t working when you were scaling from just one to ten might be the perfect program from 50 to 100. So you need to be testing to figure out what works.

And to go back to the first question, just on the outcome piece, I love the idea of incorporating managers to have them roleplay and practice. But just to tie the loop here, on getting to speak the language, any onboarding program – 12 weeks, nine months, all these things about roleplaying, I love all of this stuff – you have to embed a sales-based outcome within the program itself. So what I mean by that is have the roleplay, have the reflection, have the one-on-ones, have them practicing the demo. But within that flow, wherever it is, have the checkpoint or outcome or milestone of, “Okay, now go make your first 50 dials.” That’s what you want to be aligned with the sales manager.

There are two types of sales leaders. This is how I break them down: people that love what you do and respect training and coaching, and the ones that say they do because they have to but really they think it’s crap. They’re just kind of like, “Just get on the phone, hammer it, do what you’ve got to do, get in front of customers.” But we all know it works – especially this room. So really tying back the make X amount of dials, speak to X amount of customers, book X amount of pipeline, close X amount of business within this period of time, and in between all of those things having all the reflections. So when you’re talking about automation – and you can automate all these things depending on where you’re storing, if it’s in Salesforce or whatever it is – but if you have that, the sales leaders will be very excited to see when they’re hitting those milestones. Then you can say, “By the way, the reps that practice that demo with you on Friday”, they hit that first pipeline quota faster, and then they’re going to start listening. They’re going to start saying, “they’re doing stuff that’s getting my reps booking demos and pipeline faster, they’re on to something.” And then AB test that as you continue to scale.

SM: Just to follow up on the AB testing thing. Medallia is a feedback company, so we survey everybody who goes through everything that we do. And we’ve run I don’t know how many boot camp classes, but every one has been different because of that feedback.

MP: You have to do that. That’s the only way to get through.

Emcee: Cool. Thank you very much. That was a comprehensive answer. I love tying outcomes to the programs. We’ve probably got time for about two more questions. We’ve got about five minutes left.

Audience 3: Hi. So, David, you mentioned about TTF – Time To First.. It’s a good metric, and you try to measure it, but it brings out the problem that correlation does not equal causation. So you have so many things happening at the same company at a time. Maybe you’ve gone public, you’re scaling, your ramp times are already increasing because of the new products that are in the offering, and the way you’re trying to pivot from just selling pure connectivity versus software. So, there are so many biases and it’s easy for marketing analytics to put up a chart that says, “Oh, let’s see the ramp time of a sales rep pre-enablement. What’s the ramp time, post-enablement. “ And it’s so different for different teams. So, you said this is not the only metric, but I’m still not following. What else could we be doing, because a lot of sales reps and many people don’t understand correlation does not equal causation.

MP: Right. Actually, to speak to that, I think one of the things is you don’t put all of your things, all of your faith on a single metric.

DB: Yep.

MP: You need to have multiple metrics. So you’re looking at qualified pipeline health – is it 2x, is it 3x? You’re looking at the overall percentage of attainment of a team, so what is the participation level? If you’re accessing a first-line manager, how much of their team is attaining a quota, right? Does that grow? You need to figure out what you’re baselining first, and then what you’re measuring that against in relation to the programs and what your areas of focus are. How many of the sales – and this is again a partnership with marketing – after you’ve launched a new solution-focused messaging platform, and we’ve rolled out enablement around that solution-focused messaging platform, how many of the deals are coming back to our pipeline because that went out. It’s being able to tie it all together, but my biggest advice to you: it’s multiple metrics.

DB: Oh, yeah.

MP: You can’t focus on one.

DB: I mean, I used time to first as an example. It could be TTFD, TTSD (second deal), time to third deal, time to lose – that’s a big one, how quickly does your new rep lose a deal, because that’s actually what they’re going to learn the most from. Time to first could have been a bluebird, it could have been cooking for six months and says, “Ha, look at me I closed my deal.” Right? It’s how fast do you lose? Time to FQ – TTFQ – time to first quota attainment. TTCQ – time to consistent quota attainment. We could go on and on, but the important thing is your enablement programs that you’re building have to be tied to a metric. So if time to first deal is what’s important – in enterprise sale, that’s a nine-month cycle – that’s key. And what are the leading indicators, because you can’t wait nine months. So I’m just using one, but there are all types of metrics you can watch depending on your business. And incorporate the things that push that metric within the program itself – that’s kind of where I was going with that.

CS: One thing we talked about too is not necessarily time to first deal, but time to deal where the rep has opened the opportunity and created it.

DB: Totally.

CS: Because who knows if the rep before them did most of the work or the sales manager did most of the work, so you want to know the sales rep can do it start to finish.

MM: So two really quick notes. I agree, I have a love/hate with the time to first deal because I hate the metric. Too often sales managers close it for them. But I love it because there’s excitement around it, right? So, to your point, it’s something that everybody can kind of get. There’s some joy there. That’s great. Let’s not take away the joy. But one of the metrics that I love is what percentage of the reps are ramping? And how long does it take? What percentage are actually hitting quota? So there’s a lot of other metrics that you can do, in addition. But don’t take away the time to first deal, we have to have some balloons and champagne.