Building Value Meals Within Enablement

with Matt Schalsey,

Senior Manager of Sales Enablement, Chili Piper, Co-Founder, The Enablement Squad

In this episode, Pete is joined by Matt Schalsey, the senior manager of sales enablement at Chili Piper and co-founder of the online community, Enablement Squad. Together they discuss how to make enablement more valuable to others by unpacking everything from company acquisition to problem-solving within your program.


Key topics in today’s conversation include:

  • Matt’s background and career journey (1:09)
  • Enablement when acquiring companies (12:52)
  • Advice for new enablement professionals (17:22)
  • Defining “enablement” (20:17)
  • Why program enablement should be first (26:45)
  • Problems enablement won’t touch (30:57)
  • When enablement is the most valuable (33:47)
  • How to get connected and where to learn more (36:46)


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


Pete Thornton 0:00
All right. Hey everyone, welcome back to the SaaS Ramp Podcast. I’m your host, “Podcast Pete.” With me today, special guest Matt Schalsey. Matt, Senior Manager, sales enablement at Chili Piper, and well-known co-founder of the online community, Enablement Squad. Welcome to the show, Matt.

Matt Schalsey 0:25
Yeah. Hey, thanks. We appreciate that. I appreciate the intro.

Pete Thornton 0:29
We had an awesome introductory call to just go ahead with interesting topics, what can we unpack like not a straightforward journey into enablement, various different organizations like different org structures that could possibly be so it was a little bit harder to actually like narrow scope on this what we wanted to talk about. So maybe if they maybe it’s a three-parter over the course of time, habit. For the sake of everyone involved, knowing how strange it is moving into enablement from all the exterior functions you could possibly have done leading into this. I’d love to know a little bit more about your background, the organization’s you’ve been at, personal experiences, professional experience leading into enablement.

Matt Schalsey 1:08
Yeah, absolutely. I did about 10 years of sales prior with Verizon worked my way up through in being a district manager during some training, really finding ways to optimize how my team effectively, rose to the occasion, right from that, jumped into a marketing stint where I really focused heavily on TV advertising, sales, as well as some digital on there, jumped over into the marketing world, I worked on the agency side of the house, too, I really worked with some cool companies, Coca Cola, UFC monster did a thing for the USA archery team, as well, too. So that was really fun to like, really get myself into some different brands that are completely unheard of for somebody, like myself in Nebraska. Once my agency I got sold out, I was one of the ones that were let go and didn’t get to move on. So I jumped into a company called huddle, which is a tech startup here in Nebraska. It’s a sports analytics company. And it was really cool to see how I can make an impact there by doing the enablement stuff. And so it was really interesting on that front where I had no idea what enablement was, it was a sales job without a quota. And it had a salary that was really stable. And that was kind of something that was very important to me and my husband as we’re starting to grab our family. He’s in sales 100% commission. So I wanted to make sure that we had something that was stable and set. So I got into it, loved it, fell in love with it, read a couple books, within three months was promoted and was starting to build out part of our international team as well. So that was a really fun opportunity for me to really dive in and understand what enablement was, for me, being in Nebraska, we are not a tech hub. We are completely like, yes, people joke like to even have running water. Some days, it works. Some days it does not. It’s a complete joke. We have water all the time. But I don’t have like the full avenue that a lot of other people are getting. And so for me it was how do I branch out and really start to expand my network and understand more about this craft because there is no formal education. There is nothing with how to do this properly. We’re still trying to define those guardrails. There are, like, of course, best practices and what works but hasn’t been working for every company yet not like sales, right? Like we see very standardized practices across the board. So I think for me, I went to a conference outreaches unleash where I found Stephanie middleware, the CO the other co-founder of the enablement squad, and self-proclaimed her as my mentor, we kind of got up to this level where we were kind of like, at the peak of where we both could be. And she came up with the idea of like, well, what if we just did like, I wish there was like an enablement area, just like AOL Instant Messenger. If you do not know what that is, don’t ask it was like how we communicated back in the day. But how to AOL instant message other enablers so that way, I had it like whenever I wanted. So we’re like, well, we have slack, everybody has Slack. So let’s just formulate this entire community off of this. And fast forward almost three years later, we’re at almost seven or over 1,700 members globally, with tons of different impacts across the board. And I can tell you still, as a co-founder of this community, I still do not know almost anything or everything about enablement. I’m still one of those that are actively learning and getting as much as I try to give back to the community. So it’s a place for anybody that is really trying to find any way or anything more about enablement.

Pete Thornton 4:31
Okay. So I’ll get back up and go through it because there there seems to be kind of like three phases, and it pulled it out in sales. So like being a practitioner, kind of being on the front lines, understanding that in 10 years is no joke. Like, can you write like, it is a part of you? It’s what you do. I mean, you think about K through 12. And like what that represented in your life. So anytime you do something for 10 years, I was an educator for 10 years, like it’s just going to be in you for life. Now. You really grease the groove. So if you’re in frontlines you’re doing that for a long time. Then you move into advertising and marketing. Taking a quick pause there, the think that there is anything about trying to engage, adopt resources, activate users into the content you’re creating or the playbooks that you want to go and execute. Do you think there’s anything from advertising and marketing that you have gone and been able to brand internally to your internal customers? Is there anything there?

Matt Schalsey 5:22
100%. I think if I didn’t have the marketing experience, I don’t think I would put such an emphasis on branding and the marketing of how I wanted my programs to go. A lot of the times, like if you have a theme, or how you’re going to create the stuff, that is what carries through the motion of everybody else, as you’re starting to like do change management along the way. So I think that was a great spot. I also think more along the lines. For my marketing agency days, it was more of the strategic aspects and approach of how I actually had to correlate with these customers to see their need, execute on a solution, present the solution and then track the ROI. If that has an enablement, like whole roadmap, right, like we want to see the problem of the sales, we want to be able to formulate a solution, track it and see the close one percentage growth. So I think that holistically was probably what drove more of the initiatives from the marketing aspect versus like the actual content creation and design side of the house.

Pete Thornton 6:20
I guess the process where you’re trying to like is a piece of discovery. You absolutely. Create a solution. Try to measure like that. Right? Title. Okay. Yeah, that’s nice. That is unusual. It’s like very, very different, like not a lot of that. But you find one from every former occupation.

Matt Schalsey 6:38
Oh, absolutely. Yeah, I think with my journey, like, I think up until this point, like my very first job in sales was selling clothing at this store called the buckle. And I remember, like, they really had an emphasis on not one person leaves there. If they buy a pair of jeans, they need to buy a pair of shoes, if they don’t buy a pair of shoes, they’re buying another pair of jeans, if they don’t buy a pair of jeans, they need to buy three more shirts. And like that was our, like our mindset, right, like so. The land and expand model, I think from my very early days is now shaped into this entire process of like where I’m at today. So I think every occupation from even the even my days as a clothing sales guy at the buckle at the age of 18. To know where I’m at today, I think it makes all of an impact into how I actually operate.

Pete Thornton 7:28
That’s so interesting. So I don’t want to box myself in because Eric Markham at DocuSign brought up guide QCon. And my former athletes, a lot of them had gone into selling Cutco knives, and their men are like coach does the best night ever. I need Yeah. That’s I’m like, Hey, I get $4 an hour for coaching. Do I’m sorry. What was that once that next? But yeah, buckle and joining are two stores in the mall. And I remember them both. And you don’t walk into there as a teenager without just like, but it’s the best service in the world. And absolutely, that’s the there’s a trade-off there. Like somebody’s interested in helping you because it is mutually beneficial. There’s some incentive alignment happening there. It depends on what area within enablement you sit, but if you’re looking at comp plans, and you want to incentivize some behavior, obviously at buckle.

Matt Schalsey 8:23
Yep. 100%. Yeah. So I mean, it was that it was like a no-brainer.

Pete Thornton 8:29
That’s so interesting. And that is that’s why and it’s fine. And it is just like, a different deal. Alright, so so very cool. So and then you come in and you’ve made me make some mention of some of the organization’s you’ve been at within technology because they are there are some like household names in there.

Matt Schalsey 8:48
Yeah, absolutely. So as I mentioned, like in my enablement career, I started out at huddle, based in Nebraska. So it’s really cool to get into that at the athletic coaching realm. For those of you that don’t know what huddle is course and gone, so it’s course and gone for athletes. So it was super awesome to have that transition, which is exactly where I went to Next I went over to chorus, and worked through there for basically leading the team as my director was actually going out on maternity leave. So we brought on a customer enablement, we brought on an onboarding manager, we redeveloped part of the programs that are going on there right before the purchase, of course, and to zoominfo. So I actually then transitioned into the zoominfo world, where I helped our team and our chorus colleagues basically get acclimated into the course product zoominfo to understand the course enablement products as well, too. So although there was some differences that I had, I eventually ended up leaving zoominfo and went over to a company called lunchbox that was probably by far the most like radical shift I’ve ever done. I went into food tech, and I had zero restaurant experience, zero knowledge of the space competitors, anything like that. If you were to throw me into zoominfo or course like I can give you five different competitors of each one of those today. Yeah, but Foodtech was completely different. So that’s it. Little it really intrigued me it was something brand new. And it really like stemmed this new moment for me to be educated and really learn some new space. So it was at lunch box, they raised a series B phenomenal company, we did a really great job. Unfortunately, due to some unforeseen market shifts, I was actually part of a layoff that happened with the company, which was a blessing in disguise, because now I’m awesome. Awesomely set over here at chili pepper, leading their enablement team bringing some structures of order to the chaos, as I like to say sometimes, but it’s a phenomenal team and being 100% remote, especially within Nebraska, it’s very difficult. But chili pepper has made it so incredibly phenomenal, from a remote cultural perspective, that I don’t feel like I’m at home, I feel like I’m actually part of their office every single day, which we don’t have an office. So it’s amazing that we all feel that way.

Pete Thornton 10:49
Yeah, I’ve seen so much of that, like just content and like, either they’re doing a great job of promoting it, or it’s just so true that it can’t help but getting out.

Matt Schalsey 10:57
Yeah, I was telling a friend the other day, I was like, you go to these other companies and you like always say, the best company that you’re there and you want to drink, you’re drinking the Kool-Aid, I might have drinking the Kool-Aid, that’s fine. But truthfully, I don’t feel like it’s Kool-Aid, I actually feel like it’s a very genuine experience from a cultural shift, cultural experience, like there’s not, there’s not the clock out at five. And I absolutely don’t like the company that I’m at. But if I clock in at nine, I absolutely love the culture that I’m part of. So I think it’s one of those that I’m continuously 24/7 very happy with the cultural and the experiences that the team members have given in the responses of how hungry all these all of our sales reps are as well, the rest of the organization is with enablement. So it’s phenomenal. I can’t speak enough about how awesome the culture is their pool.

Pete Thornton 11:44
That is awesome to hear. Going back a couple steps, not on the road.

Matt Schalsey 11:48
Absolutely no, you’re good.

Pete Thornton 11:50
The acquisition. So it’s interesting, I do my first enablement job out of technology sales, business development, mid-market, enterprise b2b sales at a smaller bioscience company. And then and then into sales enablement. So it was like all of these structures and put our sales enablement back at the first company that I was moved into tech from education, and so and so, but they hadn’t been. So what we did was kind of just like level set with new leadership and bring some of these processes together with where they wanted to go. I’m just interested about what that looks like. Some companies acquire one after another after another, and they’ll have enablement personnel there as well. So what was the experience like? And like, is that almost like a subset of enablement unto itself? Like, you’re the acquisition mind maildir. You’re the one who was able to smooth the trails together kind of like dovetail to pieces.

Matt Schalsey 12:51
Yeah, with the acquisition, it was a different experience. So I actually found out about the acquisition on my very last day. So it’s really like, whoa, okay, well, I guess what I’m going back to is not what I loved, going from so significantly different there. But the one thing about the acquisition that was really interesting was zoominfo is like very acquisition, they’ve, they’ve done a lot of acquisitions. And so they have a very streamlined process of how everything was working. The one thing that we as chorus had was there was such of the like, the new startup side that there was so much still to be like transfer like knowledge from different varying people as well. But how do we document all that? And then how do we showcase that information back over to zoominfo. And so it’s really interesting with the existing team of zoominfo enablement team, they were very open and excited that this was all happening that built up a lot of information and collateral from zoominfo, or from the chorus team. So I was working with them a little bit prior. But it was awesome to see a lot of the information that I had and transcribe that over into the Zoom info world so that way, zoominfo reps knew what about this product was happening. Now the one interesting thing that I really was really kind of hard to grasp my head around, like we’ve talked about different shifts about how that company was actually going to like, migrate the course reps into zoominfo and have zoominfo start selling course. I don’t know if that was I don’t know if that’s been changed. But when I was there, we had all of our course reps still strictly on course, so is still like I was still doing my same job with the same company with the same exact people. We just had a different overhead that we were actually watching into. So it’s really interesting to see that part of the sales motion go when I jump over to like the enablement side of things I will never give. I will never say anything bad about their enablement team because that is by far one of the most structured enablement teams that I’ve ever seen. They had a process for everything that if they had a certification for a different product, they built out a new writer course if they went ahead and had like a new change in the product and you had to retake that part of it. If you wanted to build out a course you sent out a review doc and got all these opinions. It was honestly phenomenal. And I can honestly say, there was a lot of best practices that they had there that I now take into my day-to-day as I operate as an enablement, professional. But it was so amazing to see a completely different lens from just this classic startup realm that I’ve been part of for like the last two and a half years to this now structured IP owed company that has been doing enablement. Not very long, either, but has a strict process for it. And that was really interesting to see the two differences.

Pete Thornton 15:28
That is interesting. Yeah, that’s really good. Like seeing, like, gotten a consistent theme of what people have been if it’s something very small and fast growing and then snapped into something like, right, but much bigger and structured. There’s like pros and cons to each one. And if one day we get enough of these experiences, and like we didn’t codify them into Agile and Lean meats like straw. Yeah, a lot of moments of inertia behind it. Like there’s, there’s good, good overlap there. Yeah, Otterbox. I want to ask you about cheating in enablement. Be careful what you mentioned. And it made me remember so much that first enablement experience, I came in and has only had an organization for seven months, but got so much done in seven months. So when another opportunity came along with the current opportunity to simply couldn’t say no to Postman and building out the full function ground up, and then the job as well. I had to leap. But it the reason I was able to move so fast is because I cheated. I brought my wallet, I had an old green laptop with a great, there we go. And there had been almost like a year gap in some of the timepiece away or maybe 18 months. And I came back and like what is the motion? Or was it look like? And I was just able to like, like, bring us into the future. So when you went from huddle to chorus, it sounds like there was some synergy there, there was some like for like. And then at lunch box, there was like a it’s net new tech here. How would you advise an enablement professional moving opportunities, or moving into enablement for the first time? Is it worth that cheat? Or should you just like— and I call it a cheat. You know what it is. Or should you just go in and be like, hey, I need to learn everything ground up because it’ll be more ingrained? You’ll be more structured that way. Do you think there’s a best way to do that?

Matt Schalsey 17:17
I wouldn’t say that there’s a best way to do it. I don’t know if I’d recommend a way. I’d say the way that I do it, though, is like I have my way of learning. There are always the three types of learners as enablement, we always get it as a teacher as you get it. For me, it’s really understanding, like what had worked really, really well for me and my previous companies, and then how do I take and remove the puzzle pieces, essentially, from that existing puzzle, my operations and replace them with the new companies fillings and try to see if that will mold a newer picture. For me, I say that that’s probably the there are a lot of things and processes that I brought from company to company to company. And I think as I jumped to other companies, or as I’ve moved on to different companies, I feel like there’s been an improvement over the years with those different processes. As we start to navigate a lot of when I was over at huddle, I was very much on the operational side of the house, like doing a lot of like back-end operational stuff versus like the educational and training stuff. But when I jumped over to chorus, it was very much on the opposite end of the house, right? I was doing more education and training, content management, design, all that fun stuff. So when I take these two experiences, right, like huddled to court is not the exact same motion, but the product had the same mission and vision in a way. So it’s easy to kind of like, take this mindset that I was already working with huddle, and re allocate that mindset into chorus. Now, when it came down to that new, right, this is where you remove those extra puzzle pieces that have worked previously for you. And that puzzle piece doesn’t fit. That’s where you start to make a new puzzle piece and build on that grander picture. And I don’t know if I call it I don’t know if I’d call it cheating. It’s the same thing. Like if you’re going to go teach a bunch of second graders, you have that same curriculum almost every year, but how do you spice it up? Because it’s not, it’s going to be boring for you if you have to do it year after year after year after year. So how do you change that up yourself? So I think really, that’s part of it. Also going in with a new company, new mindset, no new culture? Are they do they do in person? Are they strictly virtual? Who are Mentimeter? Or do they do strictly only slack or, or zoom? Do they use teams? There are so many new elements to every single company and I think it’s just a finding a new way to adapt with the existing processes into the new.

Pete Thornton 19:38
Yeah, yeah, that’s definitely a good point. And I’m sure it’s personality is tied to are you trying to systemize something are you trying to get more variety and spice to life? Like one of the things that is tough about enablement? Is that the huge variety that goes into it like it can be so many different things? Yeah, like something we’re we’ll unpack but I’ll leave the background alone is Just interesting. It always is. Can’t help it.

Matt Schalsey 20:02
I appreciate it.

Pete Thornton 20:03
Matt, you’ll understand.

Matt Schalsey 20:05
Yeah, absolutely.

Pete Thornton 20:07
All right. So then, to that point, if you were to look at enablement as like a full landscape, like paint the picture of what enablement can be because definitions don’t do you any good. You Google it and stuff like that. It means, like, provide the right things for the right people at the right time. And one, it sounds so good, and it is so true. But it’s just like, that’s not really going to do us a lot. But again, it is so broad. So yeah, if you could paint the, like that ecosystem for us.

Matt Schalsey 20:38
Yeah, I really liked that you said: “to do the right thing for the right person at the right time.” Like that is enablement. And if you think about it, enablement has been around for years, we just have never used this vernacular and a company setting yet. So it’s something completely different. A lot of people think that ailments also replace the classic briefcase trainer that came in with the five-inch binders and gave you everything right. So we’re so much more than that now. And it’s so different. But when we’re painting this picture, we want to make sure that we’re finding elements within the company that we’re able to go ahead and enable to give people the right thing at the right time. And so when I think about this, right, like there’s always the great debate in the community right now, like, what is the difference between sales and Inland Revenue enablement? Well, that’s kind of now been defined through sales enablement. So all the presale stuff and you talked about revenue. It’s everybody that’s encompassing and the revenue journey. And so when we’re taking a grander look, right, like people are now almost taking a new step into just enablement. And what does that mean as a company level? Well, you can have various different roles. So you can go as specialized as Do you want SDR, AE AMCs enablement? Do you even want to jump over into post-sale where you could do more of the CS enablement or customer enablement? At the same time, support enablement was a newer function that never even heard of, and I have yet to see it in some other instances, but I’ve read support enablement over at huddle, which was phenomenal. And then on top of that, right, like we want to go over that we have methodology managers that are now jumping into the market. We have program managers that are leading more of your programmatic approaches. So certifications onboarding, anything else that you’re trying to do those initiatives on, you have a leadership enablement or manager enablement, how are you dealing with a top-level down and making sure that that’s good field enablement, which are typically your trainers that are going out and taking the information from your program or content enablement or content managers, and delivering that out to the frontline teams and delivering the playbooks with the managers on that side of the house to you have coaching enablement, I’ve even seen that where somebody that’s now specialized only in coaching. So, I mean, honestly, they there are so many different realms and ways to go. I think like when you talk about that definition, you can find essentially an enablement role for almost every single person, it’s about how are we taking that craft and that function to make sure that we’re the absolute best business partner for that particular role to serve them to make sure that they can do their jobs, five, whatever percentage that you want to see that increase in. So for me, particularly when I’m looking at building out my team, I obviously would love to have a program management, somebody that’s going to oversee our product certification, somebody that’s gonna oversee onboarding together. I want somebody dedicated to that because I know that there’s an impact for every new hire, as well as our existing employees to make sure that they’re continuously engaged in the product education as well. Down the road. Absolutely. I definitely want like the specialized roles, enablement, STR AE am positions, I think for that serving a specific role has had great impact, to be able to understand specifically, what are the problems that that frontline level that you’re not hearing from a manager level as well to? Like, yes, that can transcribe up. But there are a lot of times that that can get lost in translation. So how are you specifically working directly with every single one of those roles? Customer enablement? Oh, go ahead.

Pete Thornton 23:54
Okay, let me give a summary. There were six that you named off, like, like just rattled off and like, yeah, why is it it’s, like, I think we’re that support enablement. We do it as well. It was it’s a product-led growth company, Postman came in under the customer success motion, that there’s a lot of product support. There’s a lot of customer forward support there because there was 12 million developers before there was a sales lead motion, and reported up through customer success is the first time ever and everything is twisted 45 degrees is not backward. It’s not it’s just enough to make you like confused for six months. You’re like, yep, look at it like this. So we do that by kind of default and then we’ve made a transition into just the sales or because we’re growing so fast, we’re gonna have to niche down. But I heard you say role-based, like meeting just yet like you said, SDR maybe Customer Success whatever it happens to be you can break that out. However inside teams build teams cycle-based like pre and post I just go yep, based on they’ll cycle the whole motion. methodology phased, really interesting. We brought in consultants to do specific methodologies with us, as many teams have for us. If it’s a big enough company and they want to utilize this methodology, it’s way cheaper to bring somebody on full time for like two years than it is they hire that program half the time. Programs that would be like liquid you mentioned, like new hire, ramp, onboarding, certification, these types of things. And then field coaching or like manager coach on two different levels of almost direct coaching or training. Was that a correct summary anyway?

Matt Schalsey 25:35
Yeah, absolutely. I think that I did forget one of them. that I find very important. I don’t know how I forgot it, because I find it so important. But product enablement is huge. I think having Yeah, I think all of us benefit from the product at the moment. And if you’re looking at certain lenses, some people in corporate that just their sales motion, but I definitely think like a dedicated person that understands insurance, transcribes to be that Rosetta Stone from products to sales, I think is a huge motion as well.

Pete Thornton 26:00
Well, and listen, if you start to say product enablement, though, like there is another side trail that you could go on, like we help you live. Yeah, I’ve sold teams that do something in that realm, whether it’s for our customers, or for our go-to-market teams, and then some right teams. So it is, you’re probably just been smart on that one. Okay. And then, before you carry on (because I was going to ask you about value, like bang for your buck here), but you mentioned when you come in and generate a program, you always go with program enablement first, like you want to move forward with like onboarding new hire ramp certifications. Why is that first for you? It’s first for us, too, and I’m trying to determine what is it that makes that first.

Matt Schalsey 26:43
Yeah, good question. So I would say 90% of the interviews that I’ve ever gone through for enablement, I’ve always asked like, what is the first initiative that you want me to do? We’ve ever onboarding program, right? Like, we’ve all heard that. There’ll be an onboarding program, let me see what this looks like. And so I think, historically, like that just is natural first, right, I want to make sure that there’s a systematic approach for every new hire that’s coming in. Because if I understand that they can be ramped up faster and more efficiently, and then that way, I can actually track the ramp, it’s easier for my managers, then my SVP or CRO to forecast more effectively, based off of the program that I’ve done. So it’s more of a revenue-generating type thing. Now, on the flip side, right certifications, a lot of the times when I go into a company, there is especially in the startup world, right? There’s so much knowledge that’s out there, but it’s not on paper, or it’s in one person’s Google Drive or one person’s knowledge bank. And so how do we break that? How do we break the mold to get everybody aligned to understanding what the full product is? Because once you get that full product and full scope of everything, you start to think more of the value approach? How am I going to now give you one product plus the other product plus another one, right? It’s same thing. If I go to a restaurant and I ask for a burger, I can just say, ‘I want a burger,’ but the guy behind the counter should be telling me, ‘Did you want fries or a drink with that?’ And if I say no, then I’m good. But if he never offers it, I would never know that they would have an additional set of fries or an additional size drink. So him understanding what drinks were available or him understanding what type of fries like that is the exact side of the product certification. He’s now certified to be able to sell me fries, now certified to go ahead and sell me nine different types of drinks that are out there. So I think that’s like the translation that we need to make in sales. If I’m not knowing what products are out there, what features or what value does each one of those bring? How does a side of fries compliment this burger? How does this drink or this beer compliment this burger? That is the correlation that we need to start making. We wanna start building these value meals— we’ve heard of this in the food industry— to everybody else to say, ‘Hey, these are all the products that can go along with this to make it a better solution, better value, and better bang for your buck.’

Pete Thornton 28:57
Okay, okay. So like a systematic move forward. It’s just it started with new hiring ramp onboarding because that was that was the one more thing, one more piece of that, because I just would like to know the number of organizations you’ve been at and all the enablement people that you interact with on a daily basis, is that what you talked about? Through the interview cycles before you ask the discovery question of what was the first initiative be? Is it heavy in the discussions, did you find?

Matt Schalsey 29:27
Typically not. There’s a lot of times that I think as the interviewer, you should always be asking, like, what are the biggest pain points that you’re seeing now that enablement come in and fix and even ask that question that enablement can fix and what are the problems that you never thought enablement would touch? Like, what are the biggest problems that you as a sales leader are actually faced with today? And I think understanding that because enablement, we need to be lockstep with our revenue sources and revenue leaders. So understanding like what problems we are there to help collaborate or be a sounding board for, I think, is also the other side and if you don’t feel well equipped for it like, don’t like even though it’s it might be a dream job, we gotta be upfront honest and be like, Hey, listen, like, I can solve X. But I don’t know if I got y or z to be very transparent. And I think that’s where this enablement realm comes in is like, we want to be strategic thought leaders, we have now these opportunities to ask additional questions on how he would handle these type of situations. So I think that’s like the flip side of it. But you got to be more honest with yourself to be able to support your CRO or SVP.

Pete Thornton 30:26
Yeah, I like the way you position those statements. Because it’s like can fix so just like it’s not, it’s not so pie in the sky. It’s an order, the possible, but then we brought it down into a practical application. And then like the other one because they might not know all, nobody really knows very few people anyway, a small group 1,700 of us, what enablement can handle. What problems are there that exist that you don’t think enablement will touch? That’s also an excellent question. Never heard it before. I like it.

Matt Schalsey 30:56
Yeah, I always like to ask the question when I’m interviewing people is like, if you had a magic wand to fix anything in the company, or anything that in your life, what would that be? A lot of times, like, I’ve had people pause for a good 510 minutes trying to think about, like, what is the one wish that this genie could grant me? Or like, what’s the one thing I could do? It’s always fun to see their thought process. And I’m, and I try to follow up, like, if you had any more like, what would you fix with it? And then you start to get this progressive thought of like, what all is available for you to touch and make an impact on? And usually that’s your low-hanging fruit, because that’s what they’re thinking about, like, as of that moment.

Pete Thornton 31:31
Right. It is interesting to me, like throughout the interview cycles, there are these things there are playbooks, there are things that are more like, like more tip of the spear, they’re like for the existing team members, they will definitely generate revenue. And that’s what we, we typically hang in with some of those types of questions. But then when you get right down to like, what is the emergency? What’s broken tomorrow? Because we’ll prioritize this. And it seems to be a new hire ramp. And that’s like, I guess I’d liken that to the like, the like the plumbing fix in the house, it’s like that, I’d much rather order the new lighting or whatever for the office. But it’s probably going to be when that pipe breaks. And I just think these people coming in hand over fist and in hyperscale tech organizations remotely, seems to be what, what is the actual emergency? You think about these more sexy problems and then you come in and you’re like, Oh, my God, day one to job done becomes the it’s the management burden that is the true pain point.

Matt Schalsey 32:29
It is. Yeah, that manager burden is so true. If you’re coming into a team that never had an able mood for like, the amount of enablement burden that they have is uncanny.

Pete Thornton 32:40
It’s quaint when you have like the first four or five, you’re like, hey, let’s learn together. And like everybody, like workshops up on call, right? Like that. It’s really part of like the allure of a true startup. But something happens around Series B. And it’s just like, sorry, I’d still like you put it together once a year later. It’s time for a program.

Matt Schalsey 33:05
Yeah, exactly.

Pete Thornton 33:06
Okay, this is always the case: we’re past time, got more to talk about, so I’m gonna skip one of the things that we that we did and just come around to two things. Of all the ways that you could leverage enablement—you mentioned one to me earlier when I asked, what’s the 80/20? If you could take off one of these, where would you go? So what lever would you recommend as far as, if you can get to this point in your enablement program, you get most value for it?

Matt Schalsey 33:37
Now you’re talking about personally, or for a company, career-wise? Where you want to go with that?

Pete Thornton 33:42
This is based on those six categories.

Matt Schalsey 33:44
Gotcha. Okay. So yeah, so I’d definitely say like the onboarding program is like probably the number one that I start out with. I think product enablement is probably number two, right? Like if I wanted to go with my opportunity to get deeper in their product, and the tech world right now is so ever. Like, it’s constantly changing and evolving. And sometimes it’s almost at a rate where we can’t continuously keep up, especially by building content and trainings and educating our teams by whatever method of motor multimedia that we want to display this at. So I think product enablement is a good way to be like that buffer to say, okay, is this a legit opportunity for us to go ahead and educate? Is this gonna provide a revenue impact that I have to immediately educate on my team? Or is this something that I could just go ahead and say, Hey, this happened now let’s just address it and call it good. So I think with product enablement, they, they tend to have a lens of like, more of the products focus. But when I am like leading my teams, right, like product enablement is going to be very focused more on like, what is the revenue impact that this update or this new product is actually going to bring? And how do we actually need to start producing that that value impacts where customers I told one of our products and Iglu our go-to market specialists just the other day like the way that I think about Arthur the moment right as you’re building out these programs, it’s very easy for you to lose mindset of like, what is the end-user experience? And what is the seller experience versus just what the product has, right? And that’s where we come in from the speaker mindset versus value mindset. So when we have product enablement, right, I want them to start thinking about like, Okay, what is the sales reps experience by selling this product? Like, who are they targeting after? What are they trying to ideal the ICP? What is the different persona types? What is negotiation lifecycle value props that we’re going to look into. And then on the customer experience side, I think that that’s the other part that we’re continuously missing out on our field is, what is the impact and the value that the customer is actually going to start to get? And I think as we start to evolve that type of realm, we start to build more and higher value-based content for our sales reps to go ahead and deliver to the market.

Pete Thornton 35:48
Yeah, yeah. Wonderful is a lot of work in what you’re just talking about. Like, those are awesome initiatives. And then they change. And then you’ve posted was on two-week product releases when I first arrived. Two weeks.

Matt Schalsey 36:00
Oh, yeah. Oh, yeah. That’s the thing too, you have to prioritize what product releases are going to be like, high impact, low impact at the same time.

Pete Thornton 36:08
Yeah, yeah, for sure. Okay, awesome on that one. It’s a lot to take in. And I already said, we’re past time, and we could so easily go on further. So you mentioned you mentioned about like, like, gaining your personal education and why and stuff like that. So, in general, how would you recommend someone gain access to networking, education experiences, knowing that this is not a post-secondary course you’re taking? And I didn’t understand about enablement until like, two years into my SaaS software sales journey. I was there. Not knowing about it.

Matt Schalsey 36:44
Yeah, definitely. So obviously, like, I’m a little biased, but join your communities, join the enablement squad. If you have questions or want to join, connect with me on LinkedIn, and I’ll definitely send you a link to But definitely, there are sales now in the collective society, sales enablement, PRL. There are also women in sales enablement. So if you’re looking for different communities, like there’s one literally for everybody, every one of us have different content have different events, different certifications, all that fun jazz. So there are different ways to be educated through there. There’s also a ton of great new enablement, authors that are in the space too. I’ve read probably almost every single one of the books that our enablement peers have wrote. And it’s really inspiring because of course, we don’t have like a guardrail for us to say like, this is the way it needs to be done. But it’s great to get those insights and different perspectives from these other leaders that have created and paved the way within enablement as well. So I would say definitely communities, don’t be afraid to ever connect with somebody on LinkedIn. I personally, I’m not shy about that. Just always send a note like why you’re gonna connect with them new to the space want to learn more, Hey, I’ve seen a couple of your posts started following you. I felt like it would be a great opportunity for us to be able to connect.

Pete Thornton 37:54
The last book you read. You don’t have to say best or anything like that, you know what I mean.

Matt Schalsey 38:00
It was Michael Conklin’s book. And I apologize, I don’t have your book title in my head right now. But it was Mike Conklin’s book. He just released it not too long ago, it was really good. There was a lot of like, unique frameworks that are in there. And a lot of the methods that he was actually describing, were essentially more of like an enhancement to where I was actually developing a lot of my own content. So it was really interesting to see how much more like, if I just added like a pinch of salt to my own deals is basically like what Mike was doing. He was making my steak that much more perfect.

Pete Thornton 38:38
Okay, okay. I think I got him on here. I think we can. Is it leadership assessment and development? That would be county exec?

Matt Schalsey 38:45
Hold on one second. Let me pull this up.

Pete Thornton 38:50
We’re live here on the podcast. We’re doing a little LinkedIn search, little Google action here.

Matt Schalsey 38:55
Yeah, we are. It is, oh, my gosh, I can’t believe I did this, the building blocks of sales enablement. So that one has been amazing. For me, that’s probably the one that’s constantly like, near my desk all the time to revisit new materials and just be inspired, essentially. So even if it’s something that you don’t agree with, like, take it as a grain of salt to be inspired. That’s what I always like to say.

Pete Thornton 39:21
Yeah, I love that. Love that. Thank you for that tip. And then selfishly, as we kind of move into a v2 architecture across many of our different roles. We’re trying to kick some off, and then we’re trying to like restructure others to move directly towards these outcomes we’ve done man, this is a different pocket. I’ll do a solo on this and nobody even interrupts me while I just blather about what we’re hoping to do in because now you’re all pumped for it right now in the first month. Any resource or book on remote New Hire ramp remote onboard?

Matt Schalsey 39:53
The squad man like I mean, honestly, like we have a whole section that’s on onboarding and ramp. I would definitely search LinkedIn for your program managers. Those are the people that are out there. I know like Ivan Rojas from work ramp that does a phenomenal job I programs, Eric RPZ, who’s already Ada, he’s built an amazing program as well to Maria Gomez that’s at our company. She’s done a phenomenal job with our SDR onboarding programs, too. So don’t be afraid to reach out and ask for different people. There are so many different insights. And I I love the fact of enablement that none of us are ever right. All of us have the opportunity to continue to create brand new stuff and really just make it even better.

Pete Thornton 40:33
Yeah, yeah. Awesome. Okay. Great insights, cool little calls to action there at the end, too. We can get those and get those in the show notes. Also, Matt, thanks so much. Great time. Always a pleasure. This. Yeah, everybody. You’re listening. Just join us into enablement squad, get some more insights, getting that on LinkedIn, from the show notes directly. So and yeah, we’ll do it again. We’ll find out what’s happening in a year. We’ll have the right answers by then. So God, this one was just a practice. We’ll have the right answers next year.

Matt Schalsey 41:03
Fingers crossed. Thank you, Pete. Appreciate it.