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Where Enablement Goes to Die: The First-Line Manager | Ally Combs, Bretton AI

from The LeanScale Podcast with Anthony Enrico

62m 8s

Where Enablement Goes to Die: The First-Line Manager | Ally Combs, Bretton AI

Allie Combs, head of GTM enablement at Bretton AI, shares profound insights on how to build successful, scalable sales organizations rooted in true demand generation—not just demand fulfillment. She emphasizes that enablement is not about training alone, but about empowering sales teams with autonomy, data, and strategic thinking. A critical underpinning is investing in first-line managers, who act as the bridge between leadership and frontline performance. Hiring for enablement demands a focus on character, intelligence, and coachability over experience, using unconventional interview techniques to uncover genuine potential. She advocates for in-person engagement, mentorship, and intentional relationship-building to accelerate career progression. In practice, she champions agile, self-built tools like vibe-coded LMS and reporting systems to deliver faster, more flexible enablement without heavy procurement costs. The future of enablement will center on helping sales reps become business owners using leading indicators and real-time data, rather than relying on static templates. Ultimately, success stems from a culture of trust, transparency, and meritocracy where performance, not perception, drives growth—making enablement a vital engine for sustainable, scalable enterprise sales.

Transcription

9994 Words, 53549 Characters

English
If you really, really, really understand how to do true demand generation enterprise sales rather than demand fulfillment, and I just kind of fell in love with that vision. Allie Combs is the head of GTM enablement at Bretton AI, and she has one of the sharpest views I've ever heard on why most enablement programs quietly die. In sales, I do feel like it's a bit of a tricky role to recruit for. What are some principles that people should be looking out for? Because I see people probably misfire on hiring this role more than any other role in the organization. You just don't know what you're going to get because every salesperson is going to say that they're the best. I know it really is a completely different world. Like I started lean-scale in 2021. Rev-offs essentially meant sales force, outreach, gong if you were very, very progressive. Yeah, I would emphasize that a hundred times over my experience over the last nine months has been. And I think you'll see this all over like dead on the internet too, but the vibe coding you do have to be really careful with. It can be buggy, it can hallucinate, it can do weird things. All right, you were already carrying a bag and selling when you took a paycut and several emotions to go back to being a BDR and app dynamics. What did you see there that made that trade obviously worth it? That's a great question. Certainly a unique move to make in your career. At the time it was a difficult decision, obviously taking a paycut and several emotions. What really excited me and made me make that leap was this promise or this idea that they were going to invest in me, educate me, really teach me how to do true enterprise selling. In the years previous in my career, I had done channel sales, it was a bit more transactional, still very an aggregate large dollar volume of goods sold if you will, but they painted this vision for me of, look, you can own your own destiny and own your paycheck if you really, really, really understand how to do true demand generation enterprise sales rather than demand fulfillment. I just kind of fell in love with that vision of being in control of my destiny and trusted, well, I had a good impression and kind of trusted that they would do that and they did. It was probably the best career decision I made in my whole life. I think it takes a lot of foresight too, but I've always loved having a scoreboard because it's not up to whether somebody likes to use somebody has a good perception of what you're doing or they feel like you're doing a good job. It's, look at the scoreboard and who's on top and that's it. Exactly. Their whole business model on bringing in people who are coachable and really investing in them and teaching them, that's repeatable, scalable system that works, is predicated on hiring, very high performance, very driven folks and it's a meritocracy that you used to say, you know, like your success is up to you and the people who are the most successful will be rewarded. And that came to life, right? It was a very much promote from within culture, so you could see the dream happening all around you, which really made you believe that you could be that person that got promoted. And that that became true for me, thankfully, because of all the people that invested in in my learning when I was there. What did I know a lot of people that have a tough time kind of breaking out of that BDR role into that account executive role? It sounds like one, make sure you're in a place that has the right culture that is looking for those opportunities to promote. Outside of that though, is there anything beyond hitting your numbers and performing that you give as advice to a BDR, trying to break into an AE role? Yeah, and I've had this conversation many times through the years as I've talked to BDRs, or even young young people who are kind of in commercial roles trying to break through the next ceiling into the more of an enterprise space. And I think it always boils down to the person that is doing the hiring needs to look across the field and go, I trust them, I want them. It's just like when you're selling a deal and you need a champion to take your deal across the line. The hiring manager who's going to hire you for the next role needs to want you above all else. So when I was in that BDR role, and it was a very highly competitive sales force, what I started to do naturally was say, okay, how do I do the commercial role? And I started putting together, actually, this was in an office, so there was a printer. So I bought a binder, I bought tabs, and I started to print out the different templates and the sales process, assets that we were following at the time. And I started to learn, what does it mean to do POVs? What does it mean to put together pricing? What does it mean to put together a business case? And I'm a very tactile learner and it helped prepare me for that role, but I think it also gave me exposure. So I would go and I would say, hey, commercial manager, who's the best person on the team at making business cases or who's the best person at POVs? And I would just go over to them and try and talk to them and figure out what they were doing. And so I think it just goes back to that age old adage of, you dress for the job that you want, not the job that you have, and you prepare for the job that you want, not for job that you have. So in my, you know, I was still doing great in my court job, but trying to prepare myself for the next job. And I think that made a big difference. And obviously through that process, I made relationships, so other people would vouch for me. And I got to know the hiring managers at that next role level. And that was true. Like almost in every promotion that I got, that it was the hiring manager who had a relationship with, who pulled me up. And I often got pulled up earlier. I think because one, you know, you have success and sales here more likely to get pulled up, but that personal relationship was a really important part of each of those promotions, especially early in my career, trying to break through those barriers in a really competitive sales force. Yeah. And I think it's a mix of absolutely like, perform your core job, starting to reach into the new job, and then who you know, and building the trust, because it is so much easier if we have somebody on the team. It's like, hey, they're already actually kind of doing that job. Okay. If we're going to, if we're going to open up the role, they're already doing it. So let's just give it to them. Why waste time, opening up a rack, looking for other people, looking outside, you know, they're already doing it. So it, because it's, I think a lot of people don't realize it's a big risk to hire someone. So any time you can mitigate that risk by somebody already proving that they can get it done is a huge win for anybody hiring a role. I think it's so true. And I know this is a really practical, tactical point. But in today's day and age, if you're young and your sales career or you're early in your sales career for a BDR, I would highly recommend going somewhere where you can be in office with people so that you can make those relationships and you can learn faster. It is so hard to learn remote what you can learn in an office comparatively, because you can go sneak in a conference room and hide in the corner. Well, well, here appear does a presentation. I mean, you just make so many more relationships. So I would highly recommend that to, especially young and career people, BDRs, commercial sellers who want to promote quickly, go where you can actually be in an office with people and learn faster and make those relationships. I would 100% agree. And I do feel for people who are just getting into the workforce right now, because you never know what you're doing right when you start. And those relationships are everything. And it's very, very difficult to build remote. So even let's say somebody is listening and they are in a remote role, at least look for some opportunity. Like, is there a customer conference that you can request to be in person at? Is there some reason to travel to the home office if there is one? Is there a trade show that you can go to? Like, look for any excuse to go find people in person, even if you have to travel to do it. But yes, I agree, ideally, if you can get in a place that has an office, I think that would be huge. But yeah, the other thing there, if you're remote, is go ask for a formal mentoring relationship with an amazing seller or a new first sign leader. A lot of sellers who want to become managers should be, will be encouraged to take on those mentorship roles, to prepare them to be a manager, because back to your point on doing the job before you have the job, if you're saying a really successful enterprise seller looking to go into sales management, how great is it for you to have a roster of mentees that you've coached to prove that you're great coach. So I think that can be a really good work around to help accomplish some of the same as well. And then of course, just being really intentional. When you're at sales kickoff, when you're at QBRs, don't just stick to the people you know, go get uncomfortable, go meet new people, go mingle at the table with all the execs, you know, they see that too. Absolutely. I am, I would love to hear. So you went BDR, count executive, you had an amazing run in that position. And then you made a big, a big pivot, a big change into getting into enablement. How did that happen? What was drawing you to that role? What did you see where you felt you could really add a lot of value making impact? Yeah, there were the sales sort of mentor in my life that ultimately sold me on this idea. And the heart of it was, I know how hard sales can be. I know how much it changed my life and my future children's life and probably their children's life. And how fulfilling would it be to wake up every day and think, man, if I can just have the tiniest bit of impact on someone else being able to provide for their future and for their family and to be able to reach their dreams and goals, that is such a meaningful way to spend my time. And so that that's ultimately what got me to make the leap after almost a decade of selling myself. And I just fell fell in love with it quickly. I think there's a lot of people that maybe don't understand enablement very well. I think it's a really misunderstood department in the go-to-market landscape. From your perspective, what is enablement and what are the core things that you own if you're an enablement role? Yeah, I completely agree. I think it's very misunderstood. I think a lot of people have had mediocre or bad experiences with enablement. I think a lot of places have very mediocre enablement programs. And I think if we go back to just fundamentally, what is the job of enablement? It goes back to making sure that the go-to-market teams have the knowledge skills and resources to do their job. The hard part about that is that sellers, and I'm one of them, so I can say this with love, don't like to be told what to do. They go to the hit, they've got to paycheck that they want to make. They don't really necessarily want someone to tell them how to do their job. And so the enablement and the programs and the systems have to be built in a way that empowers them to make the right decisions and makes it their idea ultimately. And of course, you want to hire people who are coachable that is an essential part of making a repeatable, scalable business, is getting people to kind of operate in the same or similar way. But yeah, I would totally agree. A lot of, unfortunately, a lot of enablement programs can be kind of moderately effective or ineffective. I've seen that too, and I think I've seen a lot of people who maybe take the approach of, oh, it's a training team, and maybe they put together the training materials and they'll go over like how we're doing MedPick here or something, and then they'll record some things and send it out. I've seen that version of enablement. Then I've seen the enablement version where they are deeply ingrained in how we're selling why we're winning, why we're losing, working across sales, marketing, product, and aligning the things that the team really needs to win and even leaning in on some strategy of positioning and where to go. Are there any non-obvious things that you have done that have had a lot of value in enablement that maybe some enablement people aren't really doing or taking initiative on? Yeah, I think one of the most underrated levers, and this is more than just enablement, but it certainly should be a really foundational core component of enablement is investing in first-line managers. In front of anybody who's been a seller and you think back to that time, you went to that training session and told you to do something and it felt kind of like work, you're not sure you're totally bought in. What do you do? You probably talk to your peers, but ultimately you end up talking to your one-on-one and your one-on-one to your manager and you go, do I really have to do that? And in that moment, the change that the business is trying to drive lives or dies, right? When the first-line manager is able to inspire their reps to change their behavior intrinsically and is able to just like we do for customers connecting their pains and their goals to our solution, you kind of end up doing the same thing with sales reps to say, "Well, look, I know you're trying to achieve X, Y, and Z. Here's how this is going to help you ultimately achieve your goals." And then you work on it together. And so I think the first-line sales manager is the hardest job in SAS, in my opinion, and is one of the most under-invested areas. They just deserve all love and all the enablements and all the support that they can get. I think that makes a ton of sense, especially the way you've framed it. Your enablements can deliver die with that frontline manager. And I do think a lot of enablement teams and just companies in general, they focus on like, "Okay, how do we need to get the sales person trained, prepared what materials do they need, and really, really focusing a lot of that love and attention on that level of the organization?" And then pretty much saying, "Managers, you figured out. That's why you made your manager, right? You just do it on your own. I don't know, you needed help anymore." What are some of the ways that you have enabled frontline managers or given the attention they deserve? What does that look like when you're doing it well? Yeah, I think one that starts from the top down and it trickles at every level, right? So when you have a CRO who is truly passionate and truly invested from the top down in investing in the leaders below them, it models that behavior for the entire sales leadership team. So that practically can look like the way the CRO talks about, talks to treats their next level of leaders and all the leaders of their org that can look like how they set expectations in how their leaders treat their people, right? So it's almost like when your kids or your parenting, you don't like your kids will do what they see more than they will do what they're told. So I think that is part of like an essential part of creating that type of culture and that kind of atmosphere as they need to see it demonstrated from the top down. And then I think on a practical level, it takes time and money. You pull them out of the field which can feel very counterintuitive, especially to execs who maybe don't understand the importance or the impact of it. You have to get them away from people otherwise they will not take the time to invest and develop their own skills or they'll be leaving their training session to go onto a critical deal call. And they've got to realize like you're as a great, you are a great manager if your team can operate well without you. Your job is almost to exist to replace yourself and to build up the next sort of generation of leaders. And so one of the things I've been lucky enough to experience in my life a couple of times are those leadership trainings. I've worked for some amazing CROs before. One of my favorite career experiences have been those leadership trainings. And just to provide a specific example, I remember there was it was a two or three day period we rented out a ballroom and it was just for the leaders. And we spent two or three days on two of the three rs. Now have you heard of the three rs? I would love if you can share. Yeah, it's a very popular leadership framework, but just for anybody who hasn't heard it, it's recruit, retain, and revenue. So what that means is you recruit great people who want to learn and become better. You retain them by developing them, developing their skillset, helping them progress in their career. And then when it comes to revenue, obviously, your job as a sales leader ultimately is to bring revenue across the line. So you're in the boat with your team, being a value ad, actually helping them close deals. In that, I think it was a two to three day training, we actually really only focused on two of the three rs. That's how maniacal we were and how detailed and how in-depth we were. And now, you know, it seems like a simple concept, but there is so much skill when it comes to being a great leader. And so I just, I feel really fortunate that I've gotten to work for some great seros who one understood the importance and the power of investing. and the sales leaders, especially the first sign managers. And we're willing to take the time and the money and take people out of the field to truly invest in their career growth. And the fun part about all of this is it actually does change people's lives. - It absolutely does. I know I've been the beneficiary of some fantastic leaders that have invested in me, given me a shot. And it has fundamentally changed my life, my career, the opportunities I have for my family, it's 100%. And it's so fulfilling when you get to do that for somebody else too, give somebody a chance, coach them up, train them up, and then you see them leading. I'm curious in the ballroom, what were the two ours that the team paid special attention to? - It was recruiting and retaining. And they used to say, and this might seem counterintuitive because especially for a first-time manager, someone's natural instinct is, I was a great rep, I can make you a great rep. But what ends up happening is they get so involved in the deal, something they kind of, what we have turned before, super-reppy, where they almost step in and do the job for the rep. And the rep isn't learned that way, but it's a natural human instinct to try and take over because they know what to do to get the deal done. Now, the saying goes, if you're a great people, when you develop them, revenue takes care of itself. So there is a lot to learn still on, how do you help someone execute revenue without just doing the job for them? So they learn well along the way. That all gets much easier if you've recruited someone who's intelligent with great character and hungry for coaching and you retain them by developing them and helping them learn and feel like they're bettering themselves in their career every day. - In sales, I do feel like it's a bit of a tricky role to recruit for. What are some principles that people should be looking out for because I see people probably misfire on hiring this role more than any other role in the organization. - Yeah, it's really hard. I don't think there are any silver bullets. There's a fairly well known popular hiring framework called ICE, which is intelligence, character, coachability and experience. And again, it can be sort of a natural human nature to think, I want to hire someone who has the most experience. Well, if you ever ask a salesperson, if they're great, their answer is always that they're the best. - What, know it. - Yeah, yeah. And so when you hire for experience, which again is natural human nature to think, well, if they've done it before, they'll come here and they'll be able to do it again. But ultimately, you just don't know what you're going to get 'cause every salesperson is going to say that they're the best. And so I think of those criteria, the focus really is intelligence and more than intelligence, character and coachability. And the really tricky hard part about interviewing is you can't just ask someone, tell me about a time when you were coachable or tell me about a time when you showed that you had great character. 'Cause I'll just tell you what you want to hear. You almost have to manufacture a situation that tests for coachability or for character. I can give you a funny example. The worst interview I've ever had in my life was with that same mentor who I still talk to today and I love and respect so much and has changed my life in many ways. But I want to go work directly for him in my first enablement role. I would say he's very masterful at this type of interviewing. I remember he, at some point in the interview was kind of like, how do you think this is going? And he had purposely sort of throw off the interview and put me in a situation where I should be feeling like, maybe this isn't going as good as I thought it was. It was very reasonable for me to go into that interview thinking, I've got it, it's a slam dunk. You know, I was very successful rep. We both worked together at Epinemix before. It would have been reasonable for me to just come in with a chip on my shoulder and think, I got this, you need me, I don't need you. And so I really appreciate that he's sort of manufactured that system, I think, just to see how I would react. Do I get defensive? Or do I stop and look for coaching and stay curious and stay humble? And I remember leaving that interview, writing him an email kind of like, here's what I learned, here's what I think I would do differently next time. You know, and I think, and this is not at all to suit my own performance, just it was just seared into my brain because it was so shocking and uncomfortable for me because I would say, it just took a total turn for what I was expecting. But that's a good interview. I think that's an interesting example of. - How did you respond? How did you respond when you asked me that? I've never been asked that in an interview, ever. - Yeah, I could feel that from his energy and his body language that it wasn't going as well as I wanted it to go. So I just started, that was just very vulnerable and honest, which is hard to do when you're interviewing for a job 'cause again, what the human nature is to say is to say, I'm great and to present the best version of yourself 'cause you're trying to sell yourself into the role. But what I look for when I'm interviewing people and what I think he was looking for in that moment is I know you're great, otherwise I wouldn't be at this point with you, but I wanna make sure that you're still humble and you're curious and you're coachable and you're willing to learn 'cause we're gonna do some hard things together. You know, this is, the SaaS is a hard job. This is a hard way to make a living. So you really need people who are in the boat with you or willing to learn who are humble, who can work through conflict and do hard things. And so, yeah, I look for that myself. In fact, one of the best hires I made on my enablement team when I was hiring an evenment people, I vividly remember sort of challenging her in a panel. And her instinct was similar. She just stopped and she said, yeah, you know, and asked some questions about what we were pushing her on. And instead of getting defensive, she just stopped and she truly tried to listen and truly tried to learn. And to this day, she's one of the, I think the highest performing people I've ever had a privilege of personally hiring on a team of mine and very, very successful. I don't, you know, in her career too. - Do you have any other ways to kind of inspect those two things during an interview process? I really love that one. I might be stealing that one. Any other way to test those things about their character? - Yeah, I hope that other people, once this podcast comes out, chime in with their ideas on how to do this because I don't have all the answers myself. But some other things that come to mind when it comes to trying to understand character and coachability are understanding what people's hobbies are. What do they do outside of work? Your A-players who are high performers in life typically are high performers outside of work too. They have often unique and interesting hobbies. They have, hi, achievements. I'm thinking back to one of the other gals I worked with. She was a peer on an inanimate team that I was a part of. She was an award-winning mortician. Her father, yes, that's a real story. She's great and her father was, you know, owned a mortuary and was a mortician. And she thought she wanted to do that but it just goes to show you. There's that pattern of high performance and everything that you do. - I didn't know they handed out awards for that. I didn't know where, where's the conference and who's judging this? - Yeah, it's news to me as well. But when she said that, I thought, I'm not surprised because it's like everything she does. She puts her heart and soul into. She's a very high performer. So I think that's one way is what are your hobbies and interests and how do you spend your time outside of work? And are they doing hard things? Are they, you know, other examples I remember from interviews and from great, great people who've turned out to be great or things like sports or marathon, you know, they volunteer to put themselves in uncomfortable, hard situations where they have causes that are near and due to their heart and they raise money for, you know, start a charity. you know, starting to tear it or something like that. So I think that can be kind of interesting. I wanna know that you have something else going on other than work. - No, I think that's really helpful. Just to get an understanding, hey, what's the full body of work of this person? And just unique ways to get, because when you're hiring salespeople, usually they're good at selling themselves. So telling you what you wanna hear and knowing what the right answer is. So I think some of these little like, hey, let's throw a curve ball here or there or kind of get off the typical interview script are really, really helpful to help understand. Like, hey, is this person gonna be a good fit here? Are they gonna put in the work in the effort or are they just moving between SaaS jobs and bagging their ramp time and moving on to the next one? - Yeah, there's probably one more I'd add to that list. That just came to mind too is that remind me, based on the thing that you said is, get them out of the office. It goes back to the whole beer test. Like, especially if you have a choice between a couple people, this was advice given to me, but pick the person who you'd wanna go have a beer with. (laughs) And I think just getting someone out of the office is really helpful to just let the, hopefully let the guard down see who they really are, continue to get to know them as a person. And then I'll give you one more random one as he's keep coming to mind. I had an old CEO talk about how when he's in an interview, he will ask people about their friendships. And what he's looking for are people who have had same or similar friends for a long time. And he sees that as a sign of character of, you know, I think about my husband. He still has a guy's weekend with his friends from elementary school. They're in their mid-40s now. (laughs) And every single year they make a point to get together and they play gold and I and they go play sports and play pickleball and they play poker, you know, and they just have a ball. And they've been friends since elementary and middle school. And now they're all, you know, mid-40s. So I think that's a good sign of character too is if you kind of kept some of those same friendships. And then I'll throw you, I'll throw one more at you and you can edit these every one too. One more would be a COO I interviewed with. And I think this is fairly, fairly popular too, but understanding someone's why. And he, but he specifically had a unique take on it, which was what happened to you when you were earlier in life that made you who you are today. And he said, oftentimes there's something that happened often when you're a teenager or you're a child, whether it's your parents got divorced or they lost, you know, you're a parent lost their job or you had to move and leave all your friends behind. Like there are these really informative experiences that happen in your childhood and adolescence that can really shape who you are in your motivations as an adult. And I thought that was a really, really unique take and he said a really reliable source for him and hiring great people is understanding that. And then I'll throw one more. This is what's especially random at you. - Peace. - Yes. - One of my favorite sales leaders, and I have a couple, but Josh Reiner, who's now the CIO at tactile. I remember interviewing with him. He's the one who gave me kind of my first big job that was out in the field and the reason I moved from Dallas to Kansas City. And I remember him telling me that one of his tall, tall signs when he's interviewing reps is he will try to take a car ride with them in their car when they drive and he said he is never hired. A bad rep who, when they're driving, will switch lanes to just get a little further ahead. So you know when you're driving, and there's naturally those types of people who are willing to stay in the long line in the left hand lane even though the right lane's totally clear. And then you have people who cannot physically stand it. I'm that way. I can't handle it. I can't stay in the long line. If I can get ahead by going to the right lane to pass people, I will. And so I thought that was such a funny weird, such a funny weird example, but he said it's never let him down. So there's a bunch of random examples for you. - No, I think those are great because it has to be the non-obvious stuff that they're not preparing for. Nobody was thinking that they would have been evaluated based on how they switch lanes or not. And I was wondering, did he mention anything about the cleanliness of the car? I know that's one that I've heard before. - Maybe it doesn't matter in sales. You can have a messy car and still hit your coat. I don't know. - I don't remember him mentioning that. I do think there's some degree of a reflection of character with how clean your car is now. I would say that I have to others. My car is not that clean, but you're not going to see-- - Are the front seats clean though. That's the-- - Yeah, the front seats are clean. There's toys in the back. It's very obvious that I have children. Yeah, but there's not old food and there's not, you know, it's not gross. So I believe he did not mention that. But I do think that's an interesting sign of a character. And also a little easier to orchestrate when you're leaving an interview is like, well, you know, walking someone to their car and getting a peek in it versus actually finding yourself riding somewhere with them. But I think that's a good one too. - No, those are great. Those are great. And I think a lot of people, again, they have a tough time interviewing for this role. And knowing, should I make a decision or not, but it's because they're typically staying at the surface level that anybody's going to be prepared for and probably give you an answer that you want to hear for. So some of these non-obvious things are really helpful. I'm wondering moving to the retention side. I also, as hard it is to recruit a good salesperson, I think it's even harder to retain a good salesperson. And there are so many factors that go into that. Is the product good? Is there growth? Do they have a good territory? Do they have a team around them? Oh my goodness, to keep the good ones, because people will be reaching out to them. They can move on at any point in time. What recommendations do you have to maximize retainment of your best reps? - I actually think it's pretty simple. If they are making money and they feel like they're being developed and they're learning and they're rowing in their career, they will stay. I think it's that simple. - Are there certain major mistakes that you think people make that really compromise any of those? - I mean, I think a lot of it goes back to that relationship between the rep and their first-line manager. A really, really common mistake is letting one on one's turn into deal reviews. If we're just constantly talking about if our one-on-ones are just a never-ending deal review, I'd be learning a little bit, but you're not helping me think like a business person or to learn how to be a critical thinker and owner of my own franchise. One of the, you know, if you think back to those leadership trainings I was talking about is one of the things we would spend a lot of time is on is how do you run a great one-on-one? And how much prep that takes? A first-line manager, we used to say, you spend an hour for each rep on your team on a Friday preparing for one-on-one. We used to describe it as the most important meeting of the whole week. And if you think about it makes sense because if you can empower someone to be more effective, if you are empowering them to become a better seller and improve in their career, and they can really see how that's gonna help them make more money and reach their goals, then the rest of the week is gonna be more productive. And you can sort of scale yourself in that way, it goes back to the whole, you know, sharpen your axe before you cut down a forest, but I think so many people, and again, it's just human nature. They let, they don't prepare for one-on-ones, they show up reactively, they don't truly focus on understanding their sales reps, wise and what motivates them in order to underpin those development conversations in a really positive, effective manner. And then it's just so easy to let one-on-ones become just elongated deal reviews. And I think you gotta step back and think, okay, if I'm my sales rep, and I'm leading that one-on-one, how do I feel? Am I empowered? Am I belittled? Am I annoyed? Did that make a difference in their life? You know, so we would spend a lot of time about on how to do a great one-on-one, how to prepare for a great one-on-one, and so much of the development starts in those one-on-one relationships. - How do you have a great one-on-one? - In a lot of leadership trainings that I went to, we follow the similar formula, and it was one, understanding their data, helping them out. understand their data. And that is, starts with two major sections, which is pipeline generation, and visible opportunities or qualified opportunities is basically just what are the opportunities that you have in your pipe. And all of that is underpinned by a concept of leading indicators, which I hope every organization adopts if they don't already. Are you familiar with the leading indicator concept? I'm familiar with leading indicators unless there's something particular about how it relates to one-on-ones. Not necessarily. I guess just maybe just for anybody who's listening, leading indicators as a concept will be as pretty simple or simple, which is, here are the, you know, if you're achieving these metrics ultimately over time, we know that by achieving these metrics you are likely to achieve your ultimate goal. So some examples of leading indicators that we've had in the past and the sales capacity are, you know, 10 new business meetings a quarter, two POVs, which is proof of values or like technical evaluations, one, business value assessment, and then two deals intimate of a significant size, and two deals and upside of a significant size. And if you are hitting each of those leading indicators, quarter over quarter over quarter, that ensures you have enough new pipeline and that ensures you have enough for pipeline qualified opportunities that are progressing of a large enough size to help you meet your goal. And when I was a sales rep at AppDynamics, this was a really, really, really important big concept and they modeled our leading indicators off of hitting, you know, a few basically, if you hit these quarter over quarter over quarter, you won't just hit your goal, you'll get to 150 or 200 percent of your goal because those at times were a hard hit. Now, here's where the connection is between a leading indicator and a great one-on-one. Now, like I talked about before, as a sales rep, part of being developed by my first-line manager is understanding how to think like a business person and an owner of my franchise. So, rather than just thinking deal to deal or doing deal reviews all the time, I have leaders who spent time thinking about my business and helped model that thinking for me to say, hey, how is your pipeline generation? I noticed XYZ insights in how many discoveries you need to do before you can book an NBM or how many NBMs convert to a qualified opportunity. Hey, you're a little behind on this leading indicator. Let's figure out why. Let's get a plan together. Okay, if we look at your deals, let's actually look into, you know, your little light on VDAs or POVs. Let's figure out why or your POVs are converting like crazy, but yet you don't have enough in commit. Everything's sitting in upside. Let's dig into why. So, that leading indicator concept and being an owner of your franchise helps that one-on-one become more valuable and more developmental when your leader can model for you how to think strategically about your business. I think that makes a ton of sense. And again, going away from, hey, we're just doing a deal review over and over and over and over again, but like helping you understand how to coach yourself, how can I operate a little bit differently? Not just to meet the goal, but there's nobody who gets in sales who's not thinking about their paycheck. So how do we crush your goal and really get you in a position to be successful here? I think that applies, that's why I love sales because there's just tangible numbers to it, but I do think that concept still applies to other roles too. For sure. And if you think about the whole business model, and again, this is something that I got to live as a sales rep at Epidemic. So I'm just, that was a very formative time, but the whole concept builds on itself. If I may sales rep who got to be a part of this system and saw a leader who invested in me and really helped me be better, I took the enablement path, but probably the majority of people want to go be sales leaders. Well, what have you then modeled for them? You have modeled world-class sales leadership. So now they get promoted and they're a better leader because they've experienced better leadership and they're a much better first-line leader because they have the programs and the systems and the willingness from the topstown to continue to coach and develop them as sales leaders to be better and better, better sales leaders. And then if you think about everyone else in the whole culture and the org, when you see people's careers progress, you believe, and you want to stay somewhere that has that culture and you know, the grass isn't greener and because you see the success of others and the career of regression of others happening, you believe, hey, this is the right place and that's going to happen for me too. And when you can do that, it's such an amazing opportunity to pass that baton down. I am, the last thing I'm hoping we can cover that I think would be really helpful for anybody who's in an enablement role and a sales management role, operationally, how do you like to set up your enablement department? What tools are you using? What processes are you following? Are there any rhythms that you're running that keep you aligned with the sales organization? What does it look like operationally to run enablement? Yeah, I think there's probably a couple of founding principles or elements. I think obviously as the company scales and the size of the company changes, it morphs a little bit. I think it starts with being a really tight knit team between especially the head of sales, enablement, and revops. And coming together, looking at the data and starting to identify where in our business model are things broken and we're going to identify those problems and we're going to solve them together because they're all intertwined. So in my career, I've done a lot of coming in with a new CRO who's been hired to scale a company. A lot of times it was, hey, come be our CRO, we've got great product market set, we've got great growth, but we need to scale to get to that IPO point. And so they're coming in with that sort of playbook formula of a repeatable scale with business motion. And you can't flip a switch and make that change overnight. So there's a lot more to build that culture and that vision and it takes some time, it takes a lot more than enablement. But I would say fundamentally a good place to start is what are our, you know, kind of what's my conversion funnel of my business? Therefore where are the core problems that we need to move? Therefore across revenue, sales leadership and enablement, we're all in the same page and we're focused on moving metric, you know, kind of or like one or two metrics at a time until you slowly create that system and that culture around you. Now if you want to get a little more tactical on some of those like universal elements, I would say obviously you need a repeatable sales process that captures data in the right way so that way you're able to identify problems more smartly. And that again also has to do with revops and your sales leader. I would say practical things in the enablement world and anybody in enablement, I don't, you know, no, no, this is going to be revolutionary, but you want to have, you know, the training experiences and the tools that create those high quality training experiences, you want to make it easy for the sales, the reps and the sales leaders to do the right best thing. So practically speaking, it's having the right content management systems and having helpful programming. So there's a difference between, hey, I have kind of like a weekly or monthly updates call on sort of light-ish change management, maybe a pricing quick, quick pricing change, it's not too difficult, a system change, a tool change, things like that versus your larger programs. So we used to have as part of our rhythm, here's an example, our regular enablement and update call. But then quarterly we would always have sort of, you know, one or two bigger programs and we would do a series and there was always, you know, a-- or we were trying to drive behavior change to solve a problem that was in our business and really change behavior. So an example, one of those was rolling up the concept of a three-wise business case or focusing on discovery to try and move our conversion funnel in the right direction and for early stage cycles, things like that. So I'm throwing some random stuff at you. - That's a very, very weighty question. We can talk for hours about that. - No, I'm sure. I think there's some just foundations and I think you threw out a lot of them that are really helpful that I think some enablement teams just need maybe to know, like, hey, this is under my purview, this is something I should be doing. And one, I always just like asking, are there any tools that you're using that you're a big fan of in the enablement space right now? I also know this is a very big like build versus buy moment for a lot of people. So are there tools that you're choosing to build on your own? - Yeah, yeah, man, the world has changed so rapidly in the last 12 months when it comes to GTM tooling. One of my favorites right now is levable. Now, for context, I'm in a series B, very freshly series B startup with a small team. We have under a dozen sellers. And instead of, you know, I was the first enablement hire here. And instead of coming in and buying a typical tech stack which would be something like, you know, an LMS, a CMS, some BI tools to visualize data, some tools like, you know, people are like backstory to scrape calendars and pick up data. And there's so many tools out now that the amount of spam that I get for GTM tools is out of this world. Now, instead of spending six to 12 months and five different procurement cycles and hundreds of thousands of dollars, I just vibe coded a simple LMS and CMS and reporting stack. I'm now also integrated. We call it the GTM machine. And I own it, which means I can change the code anytime. I love having that power. I don't have time to wait on answers for someone. I don't want to have to go to IT or to other teams to wait on answers for anything. And so the flexibility that has come from vibe coding, our core stack has just been immense. And it's been, it's been really, really fun. So right now I'm using levable for that. But we do, I built my, I built our forecasting tool. I built all the reporting. We just built a lead routing mechanism. Everything's connected to Salesforce. You know, all the other tools that we use. I'm building right now a Compintel battle card chatbot. That's connected to Slack that pulls competitive mentions and auto updates, you know, from real conversations, our kill points and our perspectives and our experiences that we're hearing from customers to empower our reps to have better Compintel responses. I mean, there's just so many cool things that you can vibe code now. Like I started LeanSkill in 2021. RevOps essentially meant Salesforce outreach. Gong, if you were very, very progressive. But now it's, it's, a lot of the focus has turned into like, how can we create a data model to where Ali can build whatever tool she wants on top of it? So how do we make sure the transcripts are stored in the right way? The account information is connected in the right way. You have semantic layer that can help the AI understand what everything means, context graph to help make sure all the points are connected and everything's connected in the right way. That has become probably the biggest focus of the work to unlock all of those tools you're talking about where before it was more like, hey, the role is let's go find the tools and then we'll go implement them. Now it's, let's get the data model airtight and then let's just go get building. - Yeah, I would emphasize that 100 times over. My experience over the last nine months has been, and I think you'll see this in all over LinkedIn and the internet too, but the vibe coding, you do have to be really careful with. So I have spent and continue to keep an eye on sort of babysitting things. One thing that we're working on, like you said, is my rev off scale is actually building kind of that in between layer you're talking about because part of the way that you de-risk a vibe coded app is by having that data layer in between. So my vibe coded app doesn't need to do the really complex logic that I'm trying to get it to do because I'm trying to report on specific behavior or activity or metric results. When you take the complex reasoning out of the vibe coded app and put it into something that's really solid, like I think we're gonna do, you know, like sales like, sales like, it basically becomes sales like because it sales force to snowflake, to then, whatever you want to attach on the other side. - That's essentially what they've turned themselves into is just a massive data warehouse that everybody just already has in their company. But people aren't even logging into sales force anymore. So it's essentially sales flake, I love that. - It is sales flake. Yeah, so that's kind of our next iteration is that data layer. And there will be more to it than just that. You know, I wanna be careful about what I share, but I completely agree with what you're saying. The amazing part about vibe coding apps is the usability and the UI and the flexibility and the freedom and the power that it gives me. But you do have to be so, so, so careful, especially if you think about, you know, the stuff that we're collecting and reporting on and there will be a part of board presentations that, you know, there's a zero tolerance for error. So we're doing some cool things in that data layer. Like you said, to tighten up some of those vibe coding issues that these apps tend to have. - Yeah, no, and there's definitely a point where it's like, hey, we need a level of governance and, you know, security and, when all the boring stuff starts becoming important, that's why you should just go buy something. But if it's a fun UI layer workflow, then I think I have a good time with those. - Yeah, I will say though that I never wanna buy another Scorm tool ever for all my enablement people that are listening, I bet they're cheering or giggling to themselves. We used to pay a lot of money for all the people on my team who are building coursework to have a Scorm tool, if anybody doesn't know, there's a really popular file type that typically your learning management systems will use. So you use your Scorm tool to create the course, you upload the course to your LMS, like a mine tickle or something like that. It takes hours, days, course building coursework is takes so much longer than most people realize. In the LMS, I'm able to vibe code the courses. It's so much faster than using these old, traditional Scorm tools and it is just pennies on the dollar. So that's one thing that I think, you know, my Scorm tools might be dead. No, don't come at me on that. There's probably other people who would disagree, but I'm gonna say this. - Some of these tools deserve to die. So I'm not sad about it. Anything that you think is gonna be a trend in the future of enablement, any foundations you think will carry along no matter what AI happens to become, where do you think this is all going? - More and more, people are going to need to experience the learning and be empowered to come to the right conclusions rather than, you know, in the past, it was pretty simple, it was just simpler. Times were simpler, you know, you had a template for your business case, that's all you had. Well, now people are, it's so easy to make templates all the time. I think one of the challenges that we're gonna have as an enablement team is how do you sort of reign in and still create consistency that creates a repeatable business model when it's very easy now to go rogue and go build your own resources and build your own, build, you know, almost build your own sales culture and sales methodology. And so I think in large companies, that's gonna get harder and harder to do that. But I also think the way that people experience tools and want to learn and want to operate has changed immensely. Gone are the days of, here's a acronym for how you write a really good email to an executive prospect, they don't want that, they want a tool that does it for them. So I think, I think, there's going to be some fundamental questions of how how do you enable them to be effective and where do you start to do work for them and then at what point is that too much that you've done and you've taken away all the thinking so you know I'm super eager to super eager to see but people's expectations are certainly changing on how they learn what they learn the tools that they use what's done for them and what they have to do and I think a lot of that is good and I think some of that comes with some inherent challenges that are going to be tricky to figure out. I agree well I think with everything else in GTM six months 12 months from now we probably won't even recognize half the stuff we do and I think it's changing so fast and it's just really important to be up to date but I really appreciate everything you shared on the podcast today I think so many people have a real tough time understanding exactly what an element does and I appreciate the depth that you've taken the function and how you've helped the companies that you've helped I'm also a big fan of the 3R system that you went through especially focused on recruitment and entertainment and exactly what to do with those I am stealing half of those interview questions and techniques I don't know if I'll be able to sneak into somebody's car but I'm going to do my best and also I really appreciate the formula for a one-on-one and how to manage and bring up the next generation of leaders so Ali I appreciate you being on the podcast everything you shared and I can't wait to see what you do next in your career. Thanks it's been it's been a pleasure to be here I really appreciate you having me and for anybody who's listening please don't be shy reach out tell me what you think tell me where I got it wrong tell me tell me your perspective on things I'd love to you know meet everybody and so don't be shy please look me up on LinkedIn send me a message and Anthony it's just been it's been a pleasure working with you think real highly of you and your team and excited for everything that you're doing too

Podcast Summary

Key Points:

  1. True demand generation enterprise sales requires deep strategic thinking and ownership, not just transactional execution, and is a key differentiator between successful and mediocre sales roles.
  2. Enablement’s core purpose is to equip sales teams with knowledge, skills, and resources—empowering them to make decisions independently, not simply following rigid instructions.
  3. The most effective enablement programs invest in first-line managers, as they are the critical link between leadership and frontline performance, and their development directly impacts team success.
  4. Hiring for enablement requires prioritizing intelligence, character, and coachability over experience, using non-obvious interview tactics like behavioral scenarios, hobbies, or real-life experiences to assess true potential.
  5. A strong culture of trust, transparency, and meritocracy—where leaders invest in their people and promotions are based on performance—drives both individual growth and organizational scalability.
  6. Sales professionals should proactively prepare for advancement by learning new skills, building relationships, and engaging with teams in person to gain exposure and trust.
  7. Vibe coding and custom-built tools allow agile, flexible, and cost-effective enablement solutions, but require careful governance to avoid hallucinations, errors, or data mismanagement.
  8. The future of enablement lies in empowering salespeople to think like business owners using data-driven insights and leading indicators, not just templates or scripted processes.

Summary:

Allie Combs, head of GTM enablement at Bretton AI, shares profound insights on how to build successful, scalable sales organizations rooted in true demand generation—not just demand fulfillment. She emphasizes that enablement is not about training alone, but about empowering sales teams with autonomy, data, and strategic thinking. A critical underpinning is investing in first-line managers, who act as the bridge between leadership and frontline performance.

Hiring for enablement demands a focus on character, intelligence, and coachability over experience, using unconventional interview techniques to uncover genuine potential. She advocates for in-person engagement, mentorship, and intentional relationship-building to accelerate career progression. In practice, she champions agile, self-built tools like vibe-coded LMS and reporting systems to deliver faster, more flexible enablement without heavy procurement costs.

The future of enablement will center on helping sales reps become business owners using leading indicators and real-time data, rather than relying on static templates. Ultimately, success stems from a culture of trust, transparency, and meritocracy where performance, not perception, drives growth—making enablement a vital engine for sustainable, scalable enterprise sales.

FAQs

The most important traits are intelligence, character, and coachability—more than just experience. Hiring managers should look for candidates who are humble, curious, and willing to learn, often tested through situational interviews or personal interactions.

A BDR should proactively learn the skills of enterprise selling, like creating business cases and conducting POVs. Building relationships with commercial managers and demonstrating initiative in learning helps build credibility and trust for promotion.

In-person interactions allow for deeper relationships, faster learning, and better relationship-building with colleagues and executives. Remote roles make it harder to learn and build trust, so seeking opportunities to attend conferences or travel is beneficial.

First-line managers are critical to success—they influence team performance through coaching, development, and empowering reps to think like business owners. Enablement should focus on strengthening their leadership skills.

Ask situational questions that challenge a candidate’s mindset, such as asking how they’d respond to a difficult or unexpected situation. Observing humility, curiosity, and openness to feedback reveals true coachability.

The three Rs are Recruit, Retain, and Revenue. Recruiting great, coachable talent; retaining them through development; and driving revenue through effective leadership and team performance.

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