10 Challenges Enablement Solves For

with Pete Thornton,

Customer Teams Enablement Manager, Postman

Ever wondered if your company needs enablement? In this episode, we’re walking through ten signs that you do and how to resolve those issues. From low employee morale to scaling bottlenecks, here are the team and tools you need to optimize your business.
Play Video


You Might Need Enablement IF…

  • 1 – You’re experiencing lost revenue opportunities (1:28)
  • 2 – You have low employee morale (4:22)
  • 3 – You have low employee productivity (7:01)
  • 4 – You have low employee quality (8:46)
  • 5 – You have high employee attrition (9:51)
  • 6 – You have high management burden (12:27)
  • 7 – You would like to decrease future recruiting difficulties (15:17)
  • 8 – You would like to have future funding capabilities (17:34)
  • 9 – You have scaling bottlenecks (19:30)
  • 10 – You have misaligned customer messaging (21:18)
  • The team and the tools (23:34)


The SaaS Ramp Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at www.saasrampmedia.com.


Pete Thornton 0:06
Hey, everyone. Welcome to the SaaS Ramp podcast. We’re gonna go solo edition today, solo edition just so I can kind of share some of the things that I’ve heard repeatedly in enablement. And see if some of the challenges that I understand enablement solve for could help you. So we’ll spice it up a little bit. There’s an old comedy bit that you may remember from way back if you’re on in your years, Jeff Foxworthy and it’s like, you might be a redneck, if well, we’ll play a little bit, you might need enablement, if, and we have 10 challenges that enablement actually solves for. So we’ll go through one by one to all 10. And then at the end, I’ll offer what I offer often to heads of sales and customer success, right when they reach that inflection point of needing to move into creating the enablement function. And that is what the job descriptions might look like what that team could look like, and two of the most pivotal software, so team and tools at the end. So let’s go through these 10. And just find out how many of these you may be feeling now if you’re in those positions, or if you’re in enablement, love to understand how many of these 10 that you’ve actually sold for so far, what else you’re looking to solve for? How do you feel about the top 10? Should we change it?

Alright, so you might need enablement if, number one, you’re experiencing lost revenue opportunities. Now, this is number one, because it’s the catch-all for everything. And it’s the thing that everybody ultimately cares about. So let me narrow that down. Because there’s a lot of ways that you could be losing revenue opportunities, anywhere from the sales plays, you’re running to the messaging, all the way through until this one that I want to speak about, just because if we want to dig into the others, it’s a whole podcast unto itself. So let me talk about the one that I think is the one people don’t think about whatsoever. So the last revenue opportunity that I’m specifically speaking about here, which is very solvable, is the new hire ramp. So let’s walk through a scenario is that you have new hires coming through the front door month after month after month, perhaps week after week. And they touch revenue, they will touch in between 1 million and $2 million in revenue annually is what we find, with the average quota for a quota carrying rep typically in sales, but you could have customer success that also has revenue, retention numbers, or expansion numbers, etc. And that will be around say 1.3 million, I’ve heard him as high as 3 million, but let’s just settle it down. Because I’ve also heard some as low as 750,000. So at $1.3 million in revenue, your new hire your rep, your customer success manager, what have you is responsible for $108,000 every 30 days. So the revenue opportunity here is simply to speed them up. By 30 days to the ramp period, ramp periods are often put as 90 days or 180 days. Now, I know these are very, very just haphazard like they’re just put there for certain reasons, the 90-day period is actually put there because it’s easier to find a fit or not find a fit for keeping someone at day 89 than it is day 90. So some of my colleagues and HR former organizations have like kind of let me know, we try to see if it’s a good fit or not before 90 days, that’s what the 90-day rent period is it has nothing to do with moving to successful role based outcomes. Now the 180-day period is a little more legitimate, that gives an enterprise or strategic sales rep enough time to both ramp with or without a new hire program, as well as offer to close a deal in that time. And sometimes they’re not responsible for revenue, or as much revenue in that time period. So even the worst new hire ramp can get someone to their outcomes faster. At Postman, my organization, we increase revenue by $162,500. By increasing time to ramp by 45 days, that’s our promise for every team we work with. And that’s based on that $1.3 million dollar quota. So this is a lost revenue opportunity that’s not explicitly thought of. And so I’d like you to think about that is your first challenge.

Challenge number two, you might need enablement if low employee morale or NPS a new low employee Net Promoter Score. Okay, so this is something that we measure with customers but as an enablement lead as somebody who’s leading an enablement team, we need to measure our customers as well and our customers or internal hires, so I happen to sit under the head of both the sales leader and the customer success leader so our customers are typically customer facing roles, but and that is the most common but no matter where you sit in enablement, no matter how many teams you support, your employee morale could be measured. So fortunate In this regard, most people that are hired into fast-growing SaaS organizations, I typically deal with gist hypergrowth, organizations post a series B, typically a series B comes along, and that’s when the product adoption will be met with requests for 100%. Year over year, revenue and headcount growth, it’s just this massive hyper-growth period that lasts for at least the next three years. And that’s kind of where I like to be. That’s where I specialize. But I do find that people who come to these organizations, they’re a different breed already, they are ready to go, they’re excited, they want to be here. So this one’s a little bit more along the lines of what medical doctors consider the Hippocratic Oath, this would be first “do no harm.” So the thing that you want to do in the new hire ramp or an enablement onboarding, or ongoing enablement at this pic time period is simply not take that away, do not put any blockers in their way. Just make sure that you illuminate for them. clarify for them what their role-based outcomes are, what are they actually responsible for, because you’re hiring expensive, talented people from the marketplace, we have recruitment teams perhaps or maybe you’re outsourcing a recruitment team to bring these folks on board. And so all you need to do is simply tell them their outcomes. And even without enablement at that point, if they have their outcomes, and actually know what things they’re responsible for perhaps even giving them a few milestones. So if you can answer these questions, and you can perform this outcome, that is about all people need now in this remote world that everyone lives in now, and probably will continue to do so in SaaS moving forward, then it is nice if you can have some digital experiences to mimic what used to happen in the office. So at that point, I can recommend some call recording softwares that are exceptionally helpful to record both internal meetings as well. So they can gather some context as well as customer-facing examples. That’s number two.

You might need enablement if, number three, you have low employee productivity. So this is akin again to operate operationalizing success practices, what we do the organization I’m currently at Postman, we operationalize success practices. We have a little phrase. We say, “day one to job done.” So it’s not so important of where they start at day one, although it’s something you want to take into consideration to benchmark, but it’s where the job done is so much like employee morale pointing them to their outcomes. When you’re looking at employee productivity, you just want to find out what is the outcome and who is doing it? Well, favorite thing to do is just go find your superstars, and the people that you can model and then work backward from their outcomes, everybody will have a number of some sort or some kinds of outcomes that are measured. So there’s an indication what are your OKRs if perhaps is not as clean as a customer-facing revenue measurement? So what are your— We call them all different kinds of things, your business objectives, essentially the what do you want to do. And then who is doing that today. And my favorite thing to do is, is interview these people gather the resources that they offer. And then when possible, but not to overburden them, put them in a mentorship program with the new hire coming in, or the existing team member who would like to drive to those successes better. It always increases employee productivity, keep it simple. Make sure you’re expressing only the best practices don’t overwhelm, keep it social, make sure there’s an interaction there with another human being because a member everybody’s sitting remotely in their home somewhere alone, and then keep it successful, meaning focus on those outcomes. So that’d be number three.

Okay, you might need enablement if, number four, you have low employee quality. This is very similar to productivity. So the quality issue is not so much that they’re not getting as much done as an efficiency measure. But it’s one that the work that they’re doing is not as high quality as it should be. But you do handle it in the exact same manner. So again, organization, Matt, we take it, we take folks who are not exhibiting those exact same qualities, and we put them with the top performers, not day to day, these people are not managers, they shouldn’t have to do that. But we actually have some ways to scale that. We actually use content management systems, learning management systems, and call recording software in order to try to take these best practices and then scale them. Because we’re so fast growing, you have so many people on board now that we kind of need to do that. But it increases both productivity for any rep and quality for lower performing reps or any rep at all, but it’s just nice to have people put together simple social successful manner.

Number five, you might need enablement if you have high employee attrition. So there are a couple factors going on in the marketplace today that can affect high employee attrition and hypergrowth organizations. The emphasis is Always on hiring and hiring and hiring, bringing them in recruiting, interviewing, well, moving them through that pipeline, and then ramping them into their day-to-day roles, getting them to their proof of concept of their job done. And then of course, into full ramp. But high employee attrition can happen. So you can kind of combine two primary factors high average, remote, new hire turnover. Okay, so that’s the fact that they are remote, they can come and go without ever having to see somebody in person. In the end, we are all still human beings. And so any interactions that you have that are in person, you can say hello, you can shake a hand is really important. Like if you ask anybody about their software experiences, they’re always going to tell you about something in an office, maybe sitting in a stairwell, taking a call and that startup environment and not everybody is there anymore, may never really happened. Again, we’ll have little hubs will gather for a day we’ll have a kickoff, but they’re probably going to be able to come in and based on their digital experiences, be able to judge whether they’re going to stay or not have a very good friend went to an excellent startup. Excellent. And the terms of product have an excellent product. It’s always in the top 10 fastest-growing companies. And their product actually increases efficiency and some of these human interactions. But he told me on his birthday, that was a Friday, we met at a local brewery and he said, I will be here six days or six years, meaning I’d like to be here six years long term and SaaS, long time and SaaS software. But it’s the fact that if things didn’t change, probably by Monday, if in his second week, he did not experience a different vibe, he’d leave. And he did, he made it 40 days, as 40 days in the wilderness, as he now calls it. And that was an excellent company. So that can happen. It’s remote, new, higher turnover. And the second thing is go to market reps already have a higher turnover than other types of employees. So customer success, and sales staff, employees, team members, they have a higher turnover and sales is 18 months, on average. And then of course, we had the great resignation. Some people call it the great reshuffle, just because they’re moving from one job to the next. That probably increased it even more, but let’s just go with the 18 months, that’s short-term enough. So we’re trying to do anything we can to curtail that attrition.

Okay, number six, you might need enablement if you have high management burden. So let’s kind of talk about managers just a little bit to gain some context for this discussion. Managers are typically really high functioning high performing individual contributors that have gained a leg up into management. There are all kinds of reasons somebody might want to move into management. But if you’re an individual contributor, perhaps a customer success manager, or a sales representative, who’s doing exceptionally well for a number of years, and that does not feel like you’re making enough progress, perhaps you’ve turned over quota one too many times, and you’re just ready for another step in your career, but you’re excellent at what you do, then you might think it’s time to turn around and train other teams. It’s a form of enablement unto itself, right. enablement just means help. So you’re helping other reps, and it’s a great way to move forward. It’s like a previous athlete becoming a coach. Now there’s something about that, though, that is not quite one to one, it’s fairly well understood that high-level, individual contributors don’t always become the best managers. And so one of the problems is who not doing the same job anymore. And in a hypergrowth organization, that job can often become interviewing, hiring and ramping. So if you’re growing 100%, year over year, you’re often just trying to keep up with the people product process for all these new people. And you’re no longer on your own getting it done having your own systems. So that’s where enablement can relieve high management burden, Buddy is doing enablement. So if you do not have the enablement function, it will fall to your managers, because those are the people otherwise greeting them on the first day after they’ve gotten their dental benefits. And they understand what tools to be provisioned with the minute that’s over. And that’s often over by a 12, Eastern and Eastern Standard, then you’re going to be turned over to your manager for a one-on-one. And then it’s up to the manager to bring them from day one to job done and beyond. So relieving the management burden is something enablement can certainly do. Now, that being said, there’s a caveat here, there should be a specific amount of management burden as well, although at that time, you wouldn’t call it a burden 60, 40, 70, 30 and it tapers over time. So when they come in, if there’s a new hire ramp program in place, it should be about 60 or 70 to 30 or 40. Because you still want that manager involved in the know understanding taken care of the finer details of the things that they’re learning debriefing from those learnings. Perhaps there’s a certification series should be and then that way the managers can actually view those participate in the law. I’ve seen simulations, and they can pick up and you can kind of switch that ratio over the course of time. But of course, the new hire wouldn’t need as much then. So the burden decreases. Regardless, it’s a great piece that’s not often spoken about. That was number six.

For number seven, you might need enablement if you would like to decrease future recruiting difficulties, or enhance recruiting, we could even say, so recruitment seems to go like this and hyper-growth organizations, you’ll get new leadership annually is just a measure of the growth, there’s always a new set of leaders coming into the organization. Sometimes it’s based on a series funding, that you’ve gone from B to C, or C to D, D to E. And there’s another set of challenges that need to be taken on. Sometimes you just need another layer of management. So we’ll bring in another layer, sometimes it’s for the network. But what ends up happening is it’s an excellent place to gather excellent talent. So in will come a new leader, and with it comes a new network, excellent network, by the way, that’s well vetted already, and typically in the same space. So this is a great thing that’s happening. So there’s usually some early adopters just like there is for any product, and they come in, and then everybody else who’s waiting in the wings from that organization, and perhaps is also aware of that great leader who’s moved, just goes, Hey, how was it? I call it the recruitment relay because they go out, the one person goes out, and they come back, if you remember, really you come back and tag the next person who then runs. So they come out and back and they say, how was it? Well, how was it is typically, are you having initial success? Do you think you can sell something? What do you think of the culture? Is it going to be a good place to work for me is what that person’s asking, but they’re asking how was it? So again, the initial success is based on the clarity of the goal, and the resources that are put in play. Because if you ask somebody after 30 days, how was it? How is it 30 days is a very short sales cycle. So maybe they haven’t closed the deal yet, or they haven’t interacted with enough customers to really know. But they’ll understand about their digital experience, culture of the company, and whether they think they’re going to be able to be successful. So having enablement in play is certainly a way to engage them early and make them understand that they can be successful. That was number seven.

Number eight, you might need enablement, if eight, you would like to have future funding capabilities, funding capabilities. Funding from Venture Capitals is a venture capital firms is what kind of moves the SaaS hypergrowth world along, you can even tell where in a company’s ascent they are, roughly speaking, of course, this is a 30,000-foot view, by seeing what seed round funding a, b, c, d, they’re in. In fact, I know people who will move to a company based on their funding round and then stay at a combi through another funding round, they’ll run a cycle over and over, it’s kind of brilliant, they come in, they can be at a company for two to three funding rounds, or they’ll take it all the way through to IPO often over the course of two and a half or three years. And then they have great equity, and they’ve had a great experience. And they like that segment of the company building cycle and they go back and do it again, their personalities are suited for it, their skill sets are suited for it, they bring a network with them when they come. It’s an excellent way to move through that. So in order for a company, though, to get from one funding round to the next successfully, they need to be able to prove they’re able to scale. So that means they have to prove that they can scale their people product and processes. Well, product is trained on but people and processes are are are essentially scaled. So all these things need to be scaled, but enablement, certainly for the headcount. And for documenting and operationalizing. Scaling the processes is a huge piece. If it’s understood that you can scale then the funding can come. And that can be one it’s just one factor. But it’s a factor that enablement can actually help you overcome that you might not think of at that high of level, but pay put us put give us a seat at the table. That’s why future funding difficulties can be overcome. Now it’s number eight.

Next, you might need enablement if number nine, you have scaling bottlenecks. Similar to number eight build different let me let me kind of tease out the difference here. So growth will slow to the pace of your manual interactions. We only have so many human hours in the day, and more than hours, we only have so much energy and focus. So if everything that you need to convey to another organization can only be done through a person-to-person, face-to-face, typically in Zoom, one-to-one (could be one-to-many) interaction. Then it’s going to slow the pace of your growth. So in order to scale these bottlenecks, certain ideas must be documented, captured, made more efficient, and then move to others in a systematic manner. So when somebody comes into their day one, there should be a systematic manner in which they move all the way to their job done. Their job done doesn’t have to be their quota attained for the year, or all of their objectives met for the year, but they should have shown that they have the capability in a safe simulated environment and then live with a customer in order to do exactly what they need to do to do the job like a proof of concept before a sale or a minimum viable product for a product, then you’re going to want to have that for a new hire. And you would like to get them to that in a very nurtured manner. Like, I don’t help my daughter as much with reading as I used to because she’s reading better now. But those first few we did, we stayed with it, we stayed with the words. Same thing. It’s enablement, we’re trying to move from day one to job done. And that’s how to overcome some of the scaling bottlenecks, the efficiencies in the processes there.

All right. And last one, number 10. You might need enablement, if number 10, you have misaligned customer messaging. Okay, so let me explain. Because this is not product marketing. This is not the messaging that often comes directly from the CEO, if they have a bid for messaging, which they often do. So this is simply the messaging that we have across multiple teams. So let’s just consider the average customer buying journey. They come through, there are various people that touch if you have a business development team, they could be first, if it’s a product, lead growth organization, it may be the product itself and the messaging within the product that they experience first, eventually, they’ll move to again, part of like growth, it could be customer success first, or if a more traditional motion, could go into business development into sales, and then customer success. And somewhere along the way, they’re probably going to interact with the solutions engineer, these are four roles that you’re going to interact with at any given time. So what happens is, there are two scenarios, one, the company might not have their messaging nailed down yet, that could often be the case. But say they do. The messaging is actually there. But you have these different roles that are actually giving the customer messaging, or those roles tied together, do they all have their version of that messaging? And let’s say that they even do well, then how do you get that to the next 10 hires that come in the front door. So it’s essentially like you give them the messaging, or, and train on it and simulate and understand the nuances of it and how it works together between the roles. Solutions Engineer says this customer successes this sale says this business development says this, etc. Or they’re going to take their best guess because they’re talented. And they’re well paid. And they’re ambitious. And they’re energetic. And they’re going to come up with what they found on the website, what they found in the resources they did come upon, there’ll be in Confluence looking, there’ll be in Google Drive looking, if you have a CMS, a content management system, they’ll be looking, but if you don’t give it to them, they will make their best guess. And their best guests may be misaligned with each other.

Okay, so that is 10 challenges that enablement solves for. Okay, the last piece and I often get asked for this, so I did want to offer it on this solo podcast, solo cast, maybe that’s what it’s called, is the team and the tools. So I’m gonna label out what I think could get you 18 months along in the journey, let’s say 18 months, I’m trying to picture the majority of hypergrowth organizations, what they would need to do. And I’m going to talk about three roles and two tools.

These three roles are interchangeable, one person can do them all. Or you can certainly have teams of like in larger corporations that you’ll have already heard a podcast from DocuSign for example, large teams being able to do this global teams located everywhere, and multiple languages, etc. But let’s say it’s an I don’t even want to hazard a headcount. Yes, 250 150 employees, we’re rapidly approaching 600. Okay, how can we get this team off the ground with what team and what tools?

Okay, so for the team, you will need an enablement lead. This is often called a manager of enablement. You can say customer teams enablement. If you’re gonna include customer success from the beginning, it can be sales enablement, which is more traditional, but you will need an enablement lead give them whatever lead title you prefer. Manager is often the case head of could be another one senior manager, VP, Director however you do it but you need somebody who can then bring in the remainder of the functions. So that’s one and this person should have a sales or customer success background. This is my opinion. I do prefer if they have that, if there’s no other fun in the organization yet, and you’re going to build on somebody’s expertise, do make it where they have some background in this at some level, and also enablement experience. So those two pieces.

The second one is an instructional designer. Okay, as an instructional designer, it’s a different sort of role, instructional designers will be able to take insights that are already created, there is not a lot of creating on the instructional design side, but they can take those insights. And they can summarize pare it down and give it back in curriculum format. The benefit is of this is that you can take something that’s complex, and make it simple, make it social, and point it towards success, make it successful. That’s what I value in an instructional designer.

And the last piece is a learning management system admin, there are probably 800 learning management systems out there, they all function well enough in their own place. But a learning management system, unlike some other software’s is extremely manual, extremely necessary, but extremely manual, it is only as good as the content you put into it. It’s like a laptop with no software. It’s not going to do the trick. So you do need somebody who understands how to manipulate a learning management system and embed that content and keep it up to date. I’m talking about in hypergrowth organizations.

So enablement lead, instructional designer, LMS admin can be one person. Often is to start. It was just me for six months before we started building the team, it almost always is, but over time, you’re going to have to build out. And that enablement lead will eventually need to become to, or there needs to be a management layer under you move into onboarding, ongoing use, we call it a center of excellence and continuous enablement. But there needs to be a tip of the spear motion. And there needs to be something that scales it back to the other teams into the new hire ramp programs. So that’s the team. And by the way, this is the summer of 2022 in the second quarter. At this point, that team could cost you 350 to $400,000. Just to kind of like get that place in your mind. That’s how expensive a team is enablement lead is far and above more expensive than the others. Instructional Designer little bit less LMS admin less than that. So there’s kind of a one to three tier right there. But they’re also important in that order. And the tools, we’ve we brought on a lot of tools, at each organization I’m at, there are two that I find to be indispensable because you’re going to have to come up with a way to do it, if you don’t have these two. The first is the LMS. Let’s go ahead and talk about that. The Learning Management System is the only way to get the analytics you’re seeking and to drive new hires through a step-by-step program to certify. So that’s the way you can scale doubly take a new hire from day one to job done. And a certainly across multiple roles. Otherwise, you’re putting an enablement manager in place an actual manager, and you’re just having that person do it all, which it’s fine. But you’re going to end up using tools that you’re not able to track and see, you won’t be able to have learner feedback, there are places that you’re not able to duct tape, if you will, Google Drive will not handle this for you necessarily. So the learning management is a good one to go with. Again, they’re not terribly expensive, but they are very manual. So remember, the learning management system is great. It doesn’t solve your problems, though, the people and the playbook that you put inside of the platform. That’s what solves your problems. Okay, LMS is what we call that. The second one is expensive, okay, but the second one is a bit of a dream. The second one is call recording, the top two call recording tools are gong and chorus of the two, I do have a preference actually just so you know, it’s gone. Okay, let’s just go for it. I do prefer Gong over chorus, there are certain features that Gong has that chorus does not. And they both are expensive with chorus being a little bit cheaper. What I like about them is they’re automated, they pick up that voice of the customer, and they offer it back to all of the teams. There are ways to Folder them and automate them. You can track certain words and phrases. If you know what you’re listening for, you can put those words in, then this is brilliant. You can take Gong, you can take the voice of the customer. And you can use the services, keywords, the microservices, your engineering teams, what they’re building, what they’re responsible for building. You can take those pieces and track it all the way back to your engineering teams by tracker by keyword into their Slack channels if you’re utilizing slack, and then you can send it to them directly. So instead of a game of telephone coming from sales and customer success, asking what should be on the product roadmap and saying well we don’t think it’s important what we do. Now it’s directly data driven from the voice of the customer back to the engineering squads. And they can understand what the customer is asking for by domain or by their or have their specific area of expertise. And that is a beautiful thing, just one of many opportunities that it presents. The coaching opportunities are absolutely numerous.

Okay, so for these tools altogether, you want a whole team, it’s probably especially with that call recording in there. This is all going to run you about this could be 450,000 a year. So there is that to be thought of. But again, let’s take it back to number one lost revenue opportunities. I simply presented one option that was about your new hires. I don’t know how many new hires you’re typically thinking of, at Postman. I know, we’ll have brought on 150 new people in a few months from now. So let’s just use 100, because I like to use easy math. And let’s say instead of 162,000, which I promised, it’s just at 100,000. So take your 100,000 times 100 new hires, add a couple of zeros to it, right? Okay. It’s getting large. My math is in the millions. That might not be right, but that is a large amount. So that’s 20x already for that enablement team, they’ve paid for themselves, so do consider it.

Okay. Thanks for listening. Looking forward to the next one. Signing off.