Falling into Sales Operations at iHeartMedia

Alex Kracov: So you started your career at iHeartMedia as a seller and then eventually transitioned into a sales ops role. Can you kind of share the story of your career and how you kind of moved into sales operations?

Lish Barber: Yeah, I love this question. So I find enablement people and ops people, you kind of fall into your job some way or another. It's not like you can just go straight into enablement. So I was selling. Basically, one day, the regional president who was over 10 markets comes in to do a market visit. I was really frustrated because I was doing something in Salesforce. It was going really slow. And I'm like, why, why are we doing it this way? Why isn't anyone showing us how to do this in a better way? And so I just called him. I'm like, Hey, Mike. Can we have someone that does this for us, so we can onboard people faster? He was like, well, why don't you build a video? Figure it out. Go build a video, and then I'll share it with all of the AEs. I was like, okay. So I did it that afternoon. I come into work the next day, and my local boss at the time, he goes, "Hey, I was having breakfast with your new best friend." I was like, oh, who's that? He was like, Mike. You got a new job. I was like, wait, what? And so I literally fell into it out of frustration. But it turned out to be a really, really fun opportunity. And so I was just given lots of problems and had to think about how would I solve those problems with 100 AEs within our region.

Alex Kracov: It's an amazing story of just you being so proactive and stepping up to solve a problem. Alright. So you get this job. What do you do next? Because you've never been in sales enablement before. You've been a seller. Did you have someone kind of telling you what you should do, or how did you sort of think about the next step?

Lish Barber: Honestly, I kept getting problems. The first problem we had is: we had our local market sellers, and then we had local agencies that would send us these orders. There would be hundreds upon hundreds of orders coming in daily to these 10 markets. The first problem was like, how do we just get these orders into a system? They'll come in through fax or email. There was no eloquent system for these to put into our order entry system in Salesforce. And so he basically would just give me these problems and I'd have to come in with, like, how would I operationalize it? How would I build this into a process that could scale? And so I had no idea what I was doing. I'd grazed my knees at every single moment and would hit a hurdle. I'd be like, I don't know how to solve this. I'm going to go talk to some people that do. And so it was just that. So I just kept on getting more problems. There was our first sales kickoff. I've never spoken in front of a room of 100 people before. I just kept getting those kinds of opportunities and would figure it out.

Alex Kracov: It's amazing. I love the story of orders coming in over fax. I'm trying to build CPQ software right now. It's like, oh my god. A different time and era.

Lish Barber: Like radio, it's oldschool. Right?

Sales Enablement at Scale

Alex Kracov: Too funny. And so iHeartMedia is like a pretty big company. What does sales enablement look like at scale, especially as you kind of got ramped into this role? I mean, how many AEs were you supporting? What did this kind of operation look like?

Lish Barber: Yeah, so the first role that I started in was a regional role, and so that was supporting 100 AEs. Like any company, reorgs happen. I found myself being part of three regions, and my role didn't really make sense at the time. I was really grateful because someone advocated that I should join the corporate team. And so I started doing what I've been doing at the regional level for the entire company, for the local sellers. So there were 1,600 AEs. This new corporate sales ops enablement team were basically part of this modernization of our tech stack of how we were actually going to go to market.

So iHeartMedia was actually Clear Channel before that. iHeartRadio was just like an app that was built on top of it, and then the entire company rebranded. So we went from people that have been selling radio advertisements for 30 years now needing to learn how to use Salesforce for the first time in their career or needing to learn how to use a new application for emailing. And so there was just lots of new technology being brought into the business and a brand new way of managing your pipeline that a lot of these sellers have never been exposed to before. So a lot of my training was around sales process, teaching the sales leaders how to use new reporting and dashboards to manage their business. And so it was a lot of just going to lots of different markets and doing the same roadshow again and again, and again.

Alex Kracov: Very cool. I did not realize Clear Channel and iHeartMedia were like the same same company. Very cool.

Lish Barber: Yeah.

Alex Kracov: Big company. And so then, what does it look like? So you're at this corporate office. How did you get people at these regional offices to actually kind of, I don't know, follow what you're saying? Did you have champions in each office? How did you hold everybody sort of accountable? Because that must be hard, the corporate regional dynamic, and you're not sitting next to them. How did you sort of think about that?

Lish Barber: And who am I to tell these sales managers that have been running their markets for years and years and years, like decades, how to do their job in a different way? And so it was just selling internally. It was basically what I was tasked to do. And so it's going in, hearing their pains, doing discovery and then being like, well, hey, do you realize that you can do it this way? This would actually make it easier for you, and faster, and more efficient and more effective. And so I was just listening and then showing them, hey, this can actually be done in an easier way. It's not as complicated as you might be perceiving that it is. And so that's really what I do. It's relationship building and going in and listening and training.

Alex Kracov: I love that framework of sales enablement is so much just like internal selling and convincing and showing the value, and understanding the pain points and selling it back to them. It's a really good way to put it, yeah.

Lish Barber: Oh, my God. I usually say enablement is like a business inside a business. Because you're doing the sales part, right? You're listening. You're doing discovery. You're scoping. But then, you're also having to be the product. You're building the solution with the customer. You're like co-designing with your sales leaders. Then you're kind of the marketer at the end because you got to market it back. You got to sell it back and then track the adoption of what you've built. So it's a business inside a business.

Alex Kracov: I love that. And so it sounds like you actually went to - I think it was over 50 offices - to actually hold people accountable and do sales trainings. What did that look like?

Lish Barber: Yeah, it was crazy. I could go to it. We basically would pick a different market every week that I would go and visit and go and listen, go listen to the problems they were having and then showcase these new tools that they had to make their lives easier. Over time, I would meet different people in those offices that would become my champions. And so I got to create a new group of a role called the Regional Sales Operations leads. So, over time, as more changes came out, I had a person in each market that I could just give kind of like a rollout kick too, that could then go deliver that message and that training to the field.

Alex Kracov: Got you. It's really cool to hear this. Because every company I've worked at has been way smaller than iHeartMedia. And so it's interesting to hear kind of the different levels of sales enablement. As opposed to just one person, one office running all of it, you had to work through different people within the organization. It's just interesting to kind of hear that.

Lish Barber: Yeah, and it's a lot of the same for a longer amount of time. You don't make as many changes as fast as you would in SaaS. Because those changes, it takes a lot longer at scale. So it's a lot of just repeat, repeat until you've built that habit and pass it across the entire org.

Joining Algolia

Alex Kracov: But then after iHeartMedia, you eventually did join a SaaS company, Algolia. I think you joined right in the crazy hyperscale mode, which must have been a very different environment than iHeartMedia. Can you talk a little bit about why you joined Algolia, and what was the company kind of like at the time?

Lish Barber: Yeah, of course. So Algolia was kind of like my underdog story. I knew at iHeartMedia I was falling in love with the technology and SaaS in particular, and I just wanted to be a part of it. And so I moved out to San Francisco. I applied for all of these jobs in officer enablement, and I kept getting the same thing. Like, "No, you've never worked in tech before. No, sorry. This is too technical for you. You won't get it." Then I landed this gig at Algolia. I have to say a huge thank you to Ed and Charlotte for believing in me, and Jean-Louis Baffier, for believing in me and letting me try to do enablement at a tech company for the first time. Because it was the most technical product you could join. I didn't even know what an API was before I joined the company. I learned that really quickly. It was such a fun era of the company, because it had had this amazing plg start. And it was like, we'd had all of this pipeline. Over the time that I was there, we really had to start to build for the first time a really strong outbound motion to start to hit the newer targets that were put upon us. So it was a fascinating time to join the company. Also, while I had done stuff at scale, I had never done it across a global organization where 50% of people were in me. And so it was just a fantastic opportunity to cut my teeth and learn how to do it at scale.

Alex Kracov: And so what was that first - you mentioned like outbound was your first program you worked on. What did that look like? Were you helping them come up with the messaging? Was it more tooling? How did you sort of think about giving people this outbound playbook that they could run with?

Lish Barber: Yeah, it was a lot of trial and error. We hadn't really ever done personalized. It was a lot of spray and pray at the time. And so it was like, okay, can we use intent? How does that help us? How do we change our messaging as a result? We just started to build out all of these different go-to-market plays with PMM. So it'd be like, we have these amazing use cases we're starting to see in a very specific vertical like pharmaceuticals. You can imagine searching for the vitamins and all of those different medicines. And the search, if it's not great, you have a terrible experience because you don't find what you're looking for. And we solved that problem. And so we would have these vertical plays that we would build into this motion. We'd have a hypothesis of what our camera is, and then we'd go and see if our hypothesis worked with this play. And so it was a lot of like a science experiment, for lack of a better term.

Alex Kracov: Very cool, and it's funny. I mean, I'm still doing the same sort of outbound plays right now for Dock. It's like a lot has changed and some things have never changed in SaaS. But I guess, yeah, now we have a lot more AI and technology, I guess, to make it a little bit even more personalized.

Lish Barber: Yeah, exactly.

Sales Onboarding at Algolia

Alex Kracov: Algolia was scaling super fast. And so I imagined sales onboarding and just ramping new sales reps must have been a very key initiative for the sales enablement team. How did you sort of think about building out Algolia sales onboarding program?

Lish Barber: This was a really good early learning for me. When I first went to build out the onboarding program, I went and did interviews ever. I'm like, what needs to be in this onboarding program? I just had this laundry list of 100 things. I was trying to build almost like the perfect onboarding program, and I obsessed over it to a point that like nothing would get done. I realized, wait a minute. I just need to start with the bare minimum. And so I had to flip my whole how I've always built things to go to the field, instead of it being this perfectionist process that was something is better than nothing. Over time, that tugboat, if you can build the tugboat, it becomes the cruise ship and that world-class onboarding program. And so you start little by little. What's the most important thing they need to know on week one? They need to know why they joined the company, what the problem is that you're solving, and who cares about that problem. And so I just started to build it in that kind of form. So while we would have people onboarding on week one, some of my team was building week two. Then we'd put them for week two. And so we were literally building it as people were coming on board. Then over time, we'd go, well, this was missing from that cohort, so we're going to go and build that next. And so it became a really awesome onboarding process just through constant iteration.

Alex Kracov: How do you think about the curriculum of an onboarding program? What are you doing in week one versus week two, versus week three? How do you sort of think about ramping reps and slowly introducing them to the new company, new product, all those things?

Lish Barber: Such a good question. I think it's a misnomer to think that you can just squeeze everything into six weeks, and they're ready to go. So I started to think about what do I need to push that I really need to know, that they can talk about it and make them care about it because it's going to help them? I think about the outcomes of what we expect during a onboarding program. So we're like, if we want sellers to be prospecting by week three, what are all of the things that they need to know to be able to do that effectively? And so I'll focus the content towards that milestone.

Then the other piece is, what are the things that when you need to know how to make a recipe, you just need to know where to go to look it up and follow the instructions? There's a lot of stuff like that that we do in our day to day. People don't need to learn about building a quote in the first two weeks, right? Building a quote could probably just be like a list of instructions. Click here, then click here. And so I don't really need to do a full-live training for that. I just need to know that when they've got their opportunity and they're building that quote for the first time, it's there and they know where to find it. And so a lot of what I looked at when we're building onboarding programs is: what do I have to push, and what can be a pull resource that they just need to know exists? That's how I've continued to build onboarding programs now at all of the companies I've worked at.

Alex Kracov: You've led sales enablement now to very technical products, Algolia and then now you're at Sigma Computing. When you're thinking of sales training or onboarding curriculum, how do you think about that balance of product versus process? Are you teaching - I mean, it must be really hard. Salespeople don't know all the technical API stuff. And so, do they need to get super educated on that? Are you more teaching them say and learn MEDDIC, and here's how you do prospecting and all that? How do you think about that balance?

Lish Barber: Yeah, I mean it's a tough balance or strike, right? I don't think there's ever - no seller is ever going to feel amazingly confident in the first few weeks of a technical product. I think that takes time. What I've tended to do with a very technical product is focus on the problem we solve. What does that pain look like? How do you just do discovery to find that pain? What's the result of not solving that pain? What does that look like? Then what does that ideal state look like? So it's more methodology based for them to identify the pain and the problem, and then show them how they can talk about how we solve it. I would say that's why we also have SCs, our wonderful solution engineers. They can know all of the technical deep dive of the product. And so when I'm focusing on sales onboarding, it's really about the problem we solve and how we solve it and who cares about that problem.

Alex Kracov: When you think about building these onboarding programs, I mean, there's different types of sellers, right? There's your enterprise AE, mid-market, SMB, BDR, SDR, whatever you call. How do you think about the curriculum for each of those different cohorts of people? Because there's different maturity levels of sellers there. But then, there's also similarities, right? It's the same product they're all trying to sell. So how do you think about building that onboarding program across all those different seller personas?

Lish Barber: It's funny, I've done it in different ways. I have always found though with enterprise sales teams, like as much tenure as they've got, a lot of time, it's just going back to basics. Making sure they know how to run that first call, and they know what good discovery looks like. I think the differences and the nuances happen with - with an SMB, the motion might be so much different. Because for Sigma, for example, our velocity motion, we're talking to companies where they're building their data stack for the first time. And so that sale looks very different from an enterprise that's been using Tableau or another BI tool for years.

And so the motions are different. And so it's more about not necessarily how to teach the product differently, but what is the problem look like that's different in the segment and anchor on that.

Alex Kracov: Yeah, makes sense. I think in terms of - I think about always in terms of like Dock perspective. It's like when we're talking to founders and startups, it's like they're still building out their sales process for the first time. So I'm like helping them think through, like, what is that? What even goes into a pitch deck? Just film one demo video. And then I talked to a big public company. It's like, no, we have 1,000 demo videos for all of our different skews. We got to organize that. It's like radically different problems and, honestly, different products we got to build to solve those problems. So yeah, I don't know. Your answer resonated with me a lot.

Lish Barber: Yeah, sure.

Alex Kracov: How do you think about - do you try and push people to get on the phone really quickly and talk to customers, and just to send out emails like? Do you wait until they're fully ramped, or is it different flavors in onboarding? How do you think about that?

Lish Barber: I mean, I think it's all dependent on how the capacity model, the ramp and their quota is designed, like their ramp quota. I want them to be successful. I want them to get paid. And so I think it really, really does depend on the design of their plan and when we're expecting them to be at 100%. So onboarding can change drastically depending on that.

Alex Kracov: What's the manager's role in all this? Because their sales enablement person is leading the trainings and kind of building that curriculum. But then, obviously, all these people have managers as well. And so what's the relationship between sales enablement and kind of the person's manager? Because I assume the manager kind of has to reinforce the learnings and hold them accountable? How do you think about that?

Lish Barber: What we do is we have kind of like this accountability task thing. Here's what they're going to be learning, and here's what we're expecting you to talk about in your first one-on-one on your first week. And here's week two. And so it's driving that accountability balance with managers. The reality is, it takes a village to onboard people. It takes that onboarding buddy that's going to practice with them. It takes the Gong playlist that you're going to listen to, to show what good looks like at different parts of the sales cycle. It's all of those things. But we can't do it without the managers. They're the inspection. They are ramp accountability partners. Are they hitting the milestones? And if not, then we work together to come up with a coaching plan. So it's a very shared responsibility.

What is a Sales Kickoff?

Alex Kracov: You just wrapped up a sales kickoff (SKO) at Sigma Computing, I believe. It's something I know you've done in a bunch of previous roles - iHeartMedia, Algolia, Lattice. Can you talk about, like, what is an SKO? Why are they important? What's the goal of an SKO?

Lish Barber: So sales kickoffs, I love them. For me, it's about celebrating what's happened and getting everyone excited for what's ahead. We have these big hairy audacious goals in SaaS companies. We really have to rally behind getting everyone excited about the product roadmap, getting everyone excited and aligned on what our vision is and who we're going to be this year. So it's a mixture of those things, and then it's a mixture of sharing best practices.

And so, typically, what we've done at kickoffs is a mixture of that. Sometimes there's enablement, but that's just the start of the journey. I would never want to just do one-and-done training. It needs to be reinforced throughout the quarter. So my only advice for sales kickoffs is, if you're going to introduce a training theme, it needs to continue to echo throughout the rest of the quarter or the rest of the year.

Alex Kracov: What makes a good SKO, or what does even the agenda look like? Because, I mean, you talked about sales training there. But then I also see, I feel like - LinkedIn, you said, their sales kickoff I feel in like Las Vegas. It was like a party. I feel like I'd heard about it. So how do you think about kind of the rah rah fun experience of an SKO versus, like, okay, we're actually going to teach you some stuff?

Lish Barber: I think it's a balance, right? Because you don't get to meet everyone from the east coast or the west coast all at once throughout the year. It's like the one time to get everyone together. And so you do have to have that network. You do have to have that camaraderie built in. And so a typical day of being locked in and pulled over and going through slide where and listening to different speakers as part of it. But then, you've also got partner happy hours. You've got like award nights and all of those things, like the meals and just connecting people and the fun built in. Our recent one was in San Antonio. We had a night where we were doing line dancing. We had a longhorn bowl that you could take photos with. We really embraced the Texas theme this year. It was super fun.

Alex Kracov: Very fun. Do you think more companies should do RKOs, like revenue kickoff, and bring in customer success and marketing? Is that a trend you're seeing? How should people think about that?

Lish Barber: 100%. Our CS team was there. Everyone in go-to-market was actually at it. For some reason, we still call it sales kickoff. But, I mean, everyone is selling at some point. Right? To sell is human. We're all saying the same things, and we're talking to our customers. We're solving their problems. And so, yeah, we had everyone there. It was really good time.

Alex Kracov: Nice. Yeah, the longhorn bowl is fun. I'd love to see the whole Sigma Computing sales team doing a live dance. That'd be funny.

Lish Barber: Oh, my god. No one to see that. We were stepping on each other's toes. That was really bad.

What is Sales Enablement?

Alex Kracov: Let's get that. Good team bonding. You have a wealth of sales enablement experience across so many amazing companies. I'd love to kind of take a step back and just talk a little bit about sales enablement more broadly. First maybe kind of a dumb question is, like, how do you even define sales enablement?

Lish Barber: Such a good question. I feel like it also, when I talk to other sales enablers, it's like it's different depending on who you talk to. For me, specifically, I know I'm doing my job well if revenue is going up and cost of sale is going down. I think if RevOps is the process makers and they're driving efficiencies, enablement is the effectiveness that's doing the magic to drive effectiveness.

I think about it in like three buckets. I think of it as the first bucket being like having a team that's your business partner, right? And so having someone that's mapped to each segment or each part of the business. They're really there to listen to what are the problems, what are the themes, what's working, what's not, and communicating about resources, or planning training that needs to happen, and building out the accountability with the sales leaders to make sure that that happens. Then there's the platform enablement team, which is your tech stack, your content management solution, your LMS solution, and making sure that the enablement team is running the same process, has the Lego pieces to build the solution to drive that effectiveness. Then the last piece is program management. So onboarding is a huge program to build and sustain and to make sure that we're improving ramp quarter over quarter. Same with go-to-market plays. There's just lots of different levels and parts to enablement.

Alex Kracov: It's a really helpful framework. I kind of want to go through each of these things and dive a little bit deeper. Maybe let's start with sales training, because I know that's a big part of it. What makes a great sales training program? How do you think about the balance of live training, either in-person or on a Zoom call, or more of like on-demand training? You mentioned LMS systems where it's, like, hey, go watch a bunch of these videos and learn and come back to us. How do you think about kind of what's better?

Lish Barber: I've talked to so many salespeople over the years, and not a lot of them love spending hours in an LMS, which doesn't surprise me. There are people people. I use the LMS as a primer. It shouldn't be more than eight minutes of their time going through something. And it's to prep them for a live training. Giving them a little bit of context before they come to learn a brand-new motion, or a brand new persona, or a brand new part of the product. So I think about that first from an on-demand, and then to go into live training on what good sales training to me looks like is actionable. Right? Like if we're meeting a person because they need to practice something, they need to be doing something differently than they have been before.

The best enablement gives them actionable pieces to walk away with. I can give you an example. We did some embedded analytics training recently at Sigma, and the sales team walked away with a list of accounts that they could go after with brand new messaging that they could use for their outbound. And so, that way, our managers could be looking at, okay, did they work that account? Did our messaging work? How many SQLs did we get? That, to me, is like actually pushing enablement to have a lower bar of entry for the sales to actually go and do the stuff we want them to go and do. So I've tried to remove the friction for sellers for sales training.

Alex Kracov: I love that story. Then do you also make people do role playing? If it's a pitch or something like that, is it, hey, here's the pitch and then roleplay with your manager and do things like that? Because I feel like you often do that early on when you first join a company. Do you still make kind of, I don't know, sellers who have been there a while, if there's a new product, you would kind of make them go through that exercise as well?

Lish Barber: 100%. If it's like something that's really new, I'd rather them be practicing on each other and giving each other feedback and getting coached, versus practicing with a prospect. Right? We want the prospects to have the best.

Alex Kracov: Do you do demo certification? I remember we did that at Lattice. It might have been before you were there. But there was, I think we rolled out engagement and J Zac sat in a room. It was like this scary buyer. I even was one of them too. Then we had each seller come in and be like, "Alright, pitch us engagement." They had to pass our muster. Is that something you think is a good practice when you're rolling a new product or whatever the topic is?

Lish Barber: Yeah, I believe if it's something that they've never done before, again, getting certified and kind of like, again, having almost something that they have to go and build up to, so they have to care about it, they have to learn it because it's going to be inspected, it's one way to make sure that they can do the behavior. So I believe in certifications.

What I believe in most, though, is you can't be fully certified until you prove that you've done it in the wild. So it's all good in wild to get certified internally, but you should also be able to do it and show us that you've done it again and again and again in Gong.

Alex Kracov: One of the things I noticed at Lattice was, I felt like, I don't know, salespeople in general can only ingest so much new information and change the pitch so much. They get so comfortable in their zone. They pitch, and they win business that way. But then you introduce a new product or a new persona, and it can be hard to kind of change what you've been doing and been successful at. How do you think about that problem? How much can sales people, just people in general, kind of learn and change? Because it can be overwhelming given the amount of changes that's inherent in a lot of startups.

Lish Barber: Yeah, my last year, he always had this question to me when I feel like we should do all these things. He's like, do you think the field can really absorb that? What are the things that we asked him to do right now? I think it's that healthy balance of being real about how much change we're asking them to adopt. So it's a balance. I know that's a very nebulous answer. But if someone's saying, hey, we've got a brand new sales process that needs to get adopted, the reality is, that's going to take maybe two, three quarters to really get adopted. And so if that's the most important thing that we believe is going to impact revenue, then it should be the focus. It should be given the focus for that amount of time so that we can make them into behavior. It takes 68 days for a new behavior to become a habit. So you really do have to practice it and inspect it for quite some time before it really gets adopted.

Alex Kracov: I imagine it's also very personal to the rep. I think some reps are very good at change, can quickly adapt, on the fly. Then others, it just takes a little bit longer. That's to, some degree, just people's different styles and learning styles.

Lish Barber: Yeah. Well, and also similar to sales, right? Again, enablement is internally selling. If I know that someone's a detractor, a blocker, and then I'm not going to be able to get them to adopt something, I go find my champion. I go find that tiger team, and I will prove to them with data that this way is the better way. And so, again, always be selling.

Alex Kracov: You mentioned sales process there. I'm curious, like, do you have a favorite sales methodology? There's so many that go around: Sandler, MEDDIC, Force, Challenger. How do you pick one that's right for your business?

Lish Barber: I've become agnostic, because every company has wanted to do a different one. I also think that there are certain methodologies that are better for different types of businesses. So if you have a very high velocity sales motion, and you have sellers that are maybe earlier in their career, Sandler is really good for the basics and the fundamentals and for that velocity motion. If you've got a really complex sales cycle, you're selling into the enterprise, you probably want to use something like a Force management movement pick. And so yeah, I've used a lot of them. I keep them close to my chest at this point, because CROs might want a different one, and I want to make sure they stay open-minded.

Alex Kracov: Yeah, I think they all work to your point. I mean, it just depends if do you believe in it. Do you follow it? Is it the right for whatever segment you're going after? So yeah, that makes sense. Sales enablement, I have found, is just inherently so cross-functional. You're working with so many different people within the sales org, within kind of across the company. From your perspective, who are those cross-functional personas that you sort of work with most closely?

Lish Barber: Product marketing, sure. RevOps is my ride or die. Then, obviously, all of the managers for the teams that we work with. Because we can't do without them. So those would probably be my top cross-functional stakeholders. And if I've forgotten someone, I'm very sorry.

Alex Kracov: And so I'd love to kind of go through each of those. Like product marketing, what does that relationship look like? How do you work with the product marketing team?

Lish Barber: Right now, we have a bi-weekly meeting where we're sharing - we'll do roadmapping together on a quarterly basis to make sure. Because the reality is like the work we're trying to do, whether it's a problem we're solving that's being driven from sales leadership that might need PMM support, or product is launching a new thing that's going to need sales enablement support, our roadmaps overlap. The same can be said for our RevOps partners. They might be updating a new process in our systems or our tools. They might have CPQ that they want to update and rollout. So all of those partners, we all impact each other's roadmap. So it's silly to not be roadmapping with them and then finalizing a forecasted roadmap, because we should be flexible, and getting that signed off. Like, are we working on the right things? Because this is what we're going to hold ourselves accountable to. So that's what PMM and enablement looks like today.

I like to have the gray between the two teams as well. Because if we are aligned on what we're trying to achieve, we can share the work. Sometimes there's things and certain companies where it's competitive lens and PMM, sometimes I've seen it land in enablement. And it doesn't really matter, as long as the field is getting what they need to be successful.

Alex Kracov: Yeah, it's interesting how your sales enablement is sort of caught in the middle between all these different functions. Imagine the payments are coming to you. We got to launch this product. We got to train the sellers. Then RevOps is like, "We bought this new software. Train them on this." And so it must be so interesting to kind of balance all those different requests at the same time.

Lish Barber: Sowing the field is what I call it. Is it a revenue-impacting thing? And if it's not, we got to say no. Or, we've got to go back and go, are we working on the right things? Because, theoretically, if we're all trying to drive revenue, we should be somewhat aligned. So it's a lot. It's a lot of trade offs.

Alex Kracov: And you try and set up really clear guardrails of who does what. Like product marketing always makes the deck for the training, but sales enablement will set up the session and invite the right people. Do you try and define those roles and responsibilities very tightly, or do you try and keep it more loose and open-ended depending on the situation?

Lish Barber: I try to keep the workflow of a process pretty, pretty tight. So for example, when we're doing a product market launch, we kind of know who's roles are what in a product market launch. If it's like a go-to-market play, that might look different. But we just align on, like, here are the motions we know we're going to work on as teams together. What makes the most sense, where are our strengths as teams, and define that upfront with a good old racy, and then away we go.

Alex Kracov: Love a good racy.

Lish Barber: I know.

How to Be a Strategic Business Partner

Alex Kracov: Then you mentioned one of the key roles of sales enablement is being just a business partner to the sales managers, the sales leaders. What does that look like? Are you just constantly meeting with them to kind of figure out what their top competitor they're dealing with or their top issue of the day? How do you kind of go about being a really good business partner to key stakeholders?

Lish Barber: Honestly, if I was doing that, I would be really reactive. My goal is to try to give as much value as I can to a sales manager. So while I want to listen to what they are hearing, I also want to come with insights. I use data to do that. So I want them to be aware of problems they may not have even realized they had through data, and then ask them do we want to solve that, because we think it's impactful to do so? I think it's a healthy balance of both. But if it's just us coming to them with how can we help, how can we help, you become the cleanup crew. And you become the order taker. You don't become the strategic partner? I think there's so much people that fall into the order taker help bucket because they don't know how to use data, or they don't understand sales math to be more proactive with their sales partners.

Alex Kracov: Got you. So you're looking at all the sales data, the funnel data and saying, hey, our close rates are falling off, or these things are in trouble. Then here's some programs and ways we can attack that problem.

Lish Barber: Yeah, using conversational intelligence. That's a huge one for us. Also, there's a lot of this sales funnel math looking at that. But also just quantifying pain as well. If a sales leader says, like, no one knows how to pitch this new success program that you're launching, I want to go and verify that that's actually a pain. So I'll go and look at conversations that have been recorded and see how many times it's been mentioned so that I can make sure that it is a true pain, or it's not. You'd be amazed at how many things you end up not doing because that's just one person versus an entire field.

Sales Enablement Software

Alex Kracov: I'd love to switch gears and talk about a topic that is near and dear to my heart - software and sales enablement software. Maybe I'll even do my own product discovery in this part of the conversation. I'm curious. Like if you had a small budget and it's just like, what are the core sales enablement softwares that you need to buy? You mentioned a few in this conversation - content management, conversational intelligence, learning management. Are those the big three that you need to purchase as part of building your sales tech stack? Are there others? How do you think about the core of the sales team?

Lish Barber: I could not do a proactive job without conversational intelligence. So that's always going to be the first thing I go for. The LMS is probably number two, because that's how I'm going to build scale for my onboarding programs, or pre-work, or post-work. Although I do think if you were being really scrappy, you could still do a lightweight LMS for just libraries in your conversational intelligence tool. CMS is the last one for me.

I'll have to be honest. I'm at a point where I've bought three of them at this stage, and I wouldn't buy them again. I know it's a very controversial thing for me to say as an enablement person, who has all of this content that I'm trying to get into the hands of the salespeople at the right time. But I've been yet to find a content management solution that's really solved the problem. No seller actually wants to be in another tool. They already have so many. And so I just see this big theme and the enablement space of just like this consolidation of all technology. It's an interesting trend that I'm seeing and feeling.

Alex Kracov: Then where has all the content go? How do sellers find all the stuff product marketing is making? Do you just put it in Google Drive and call it a day? How do you think about that?

Lish Barber: Right now, it's in a CMS. But it's a bear to manage because we're such a small team, and it's got all the bells and whistles that we don't use. But in the future, we're actually toying with the idea of using our own product to build a content management solution. So that could be an exciting new venture for us as a team. I think about the amount of content that actually is used during a sales cycle. The reality is: it's like all of the slides that you've built for a sales team - most salespeople use maybe 10 slides during a sales cycle - do they actually need the 100-slide deck repository? It's just a question that I'm starting to ask more and more.

Alex Kracov: Yeah, this is not to plug Doc. But this is how I think about it, too. It's like, yeah, you have this huge library of stuff that you barely use. I think one thing we have found with Dock which has been pretty cool is like you have this actionable template that you can just use from client to client to client. It's a subset of the resources. It's not the ones, like the thousand in the backlog. So I don't know. That's how I think about it.

One thing I always ask myself, too, is like, why does sales need a separate system for all this stuff? Why does all the content and even learning management, why can't that just go in the company-wide wiki or the company-wide learning management system? Why does sales need its own dedicated system for that? I'm curious if you have an opinion on that.

Lish Barber: I mean, I don't, if I'm being honest. I'm starting to realize more and more that I don't know if they do. So it's something I'm still trying to figure out, if I'm being honest. I haven't seen it really drive more efficiency or effectiveness for the field by having this big governed thing where the rep still want to have agency to change things and make it more personalized, the conversations they're having. So I don't have a good answer there.

Alex Kracov: No. It's super interesting to hear your perspective on it even if it's got to like, I don't know. I guess, what is sales enablement role in buying and purchasing and implementing software? Is it usually RevOps who goes out and buys it, and then you're kind of helping enabling and implementing that process? Are you buying software? Who's doing what within the org in your experience?

Lish Barber: It's been different in every single company I've worked at. At Algolia, it was like very much I have my sales tech budget. I got to pick the LMS. I got to pick the CMS. I got to pick the conversational intelligence tools. At Lattice, it was a big partnership between our L&D team and picking our LMS. Yeah, I think, honestly, I've actually done a lot of the buying in hindsight. At Sigma, I've walked into a lot of tech that I'm trying to evaluate if it's the right technology we keep long term. And so a lot of it is just like, again, going back into discovery mode. What are the reps like? What do they need? What's slowing them down? And just aligning with RevOps if we've got the right solution in place to them today.

Sales Enablement Careers

Alex Kracov: I'd love to switch gears and talk about sales enablement careers. I'm curious. From your perspective, what type of people thrive as a sales enablement person?

Lish Barber: I think you have to be really, really, really organized and okay with a little bit of chaos. It's funny. I think like a lot of people see enablement, they only see the output, which is the training. They don't see all of the project management that goes into it, all of the discovery. You have to do all of the content you start to build in the background and all of the alignment and buying you have to get with your stakeholders.

Sellers make great enablement people if you're into doing that discovery. But I don't think it's the end all be all. I've had people that have been BDRs that have been amazing sales enablement people. I also think it depends on what part of enablement. Going back to the three pillars that I say, I think they require different skill sets. I think there are certain teams where you're going to get had a buy in if you haven't walked in their shoes. To go in front of an enterprise sales team and enable them, and you haven't done enterprise sales, that's a really tough sell.

Alex Kracov: I'm curious, why have you decided to have a career in sales enablement? Why do you love sales enablement so much?

Lish Barber: Because I'm a sadist. I'm kidding. Honestly, I love problems. I love problems so much. I love making things that are really unclear have that clarity for people. I love being a mad scientist and going: if we tweak these things and we give them these assets, does it actually drive the outcome? I just get fascinated with that process.

When to Hire Enablement

Alex Kracov: I'd love to end today's conversation with a question I'm wondering myself as I scale Dock, and maybe a question for other founders out there as well. When do you actually bring on a dedicated sales enablement person? Because I'm doing a lot of that sales enablement myself right now. We have a three-person sales team. At what point in a company's lifecycle do you think it's time to bring on a proper function for sales enablement.

Lish Barber: When you feel like you've got product market fit. Because that's when you're going to want to go and pour gasoline on the fire, right? And to pour gasoline on the fire, you need someone that's going to help you scale. Typically, I find that enablement gets on board too late into that journey. And so then they have no time to build. And for those people that fall in that situation, it's the tugboat first before trying to build the cruise ship. So that would be my advice. The moment you feel like I've got product-market fit, I'm going to go pour gas on this fire. You need enablement. They're with you.

Alex Kracov: Awesome. Well, thank you so much for the wonderful conversation today, Lish.

Lish Barber: Yeah, Alex. Likewise. This was fun.