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If you think outbound is dead, you’re either lying or you’re bad at it.
Quotas keep rising, your people are grinding, and the pipeline isn’t growing. It’s an equation that drives you mad. While everyone wants more opportunities, only a few know how to build an outbound culture that delivers.
I’m Todd Busler, former VP of Sales, now co-founder of Champify, and I’ve spent my career sharpening how to build a company pipeline that’s self-sufficient.
On this show, I’m talking to sales leaders who have cracked the outbound code. They’ve built an outbound culture beyond their SDRs and scaled repeatable systems that drive real pipeline without relying on hacks.
We’ll break down the winning plays, processes, and frameworks behind growing that outbound muscle to help you get results faster.
No fluff. No hacks. Real strategies from real people who have done it so you can stop guessing and start opening.
John Ley (00:00):
The point of the story is if you are so certain that your product is going to be a really good fit, it's not just a SDR sequence. Let me call and email a few times and I recycle it back into the account pool once I'm done. It's a no. You should pull out every trick in the book because we're so certain that it's going to be a really good FA if we get 'em on the phone.
Todd Bustler (00:24):
Everyone wants to build stronger pipeline, but only a few know how to make it happen. If you're listening to this show, outbound is not dead, you just need a little help building a system that actually works well. You're in the right place. I'm Todd Bustler and on this show we're breaking down the plays, processes and frameworks behind Repeatable Pipeline growth straight from the people who've built it. Let's get into it. Hey everyone. Really excited to introduce Johnny Ley to the show today. This is a little bit different than previous episode. He's an enablement leader, right? And any successful outbound function nails the enablement and training organization. John's the perfect person to explain how that function works and if you're a sales leader, SDR leader, how to get the most from the enablement function. He's had a great run at Square building the entire SDR organization, huge parts of ops and enablement, and then he was brought into Brex by their previous CRO, Sam Blonde to be his right hand man. In this episode, he cover what exactly was brought into Brex to solve, what role does enablement play in a well run sales organization, how he enables leaders, what he decides to focus on and how and advice for sales leaders, VPs, CROs, getting the most from enablement. Enjoy.
John Ley (01:44):
Well, yeah, so when I first started at enablement, my boss, Sam Blonde, the CRO. I was an opportunistic hire. He didn't really know what to do with me admittedly, and so he told me just go survey the go-to-market teams and figure out what's not working and fix it. That was high level and so I took that literally and I would join the sales team meetings and I'd have the sales manager ask the AEs to write down what's working and what's not working. I would see that 24 hours to find the meeting. I would show up at the slide and it would be a list of what's not working and I would make sure the room agreed with, is this the number one thing that's not working for you guys? And everyone would go on rants, and this was not training related. This was our turnaround times with the finance to get our deals approved is taking way too long.
John Ley (02:32):
I work with the ops and the risk team and the process to communicate with them is broken. I don't have any way to quantify savings when I get into rebate conversations, like real shit that would happen on a day-to-day basis that would just have them walk into quicksand. And so my first project, I remember it was organizing Salesforce case management, so we had a communication path with our risk team, nothing enablement related. It was something that once we shipped, it saved people a ton of time. So that's a good place to start is what I would say.
Todd Bustler (03:04):
It's interesting.
John Ley (03:05):
On it. What's not working. I would have sales reps tell me, dude, that is so much more helpful than doing a Zoom and doing a discovery training or doing a, here's the five best principles for demo. They're like, just fix the shit that's broken for us right now.
Todd Bustler (03:20):
Why do you think some of those managers weren't able to fix that? Was it because you were just talking across all of the different teams? What enabled you to go do that? Or is it just because you had the ear of the CRO?
John Ley (03:32):
Two things, one is the ear of the CRO help, but two is I was just more poised. God bless the people. I was a little bit more poised. I was a little bit more cross-functional. I could empathize when sales leaders would try to fix it, they'd come in so hot and they didn't know the solution. They would just be like, this is broken. What's going on? This needs to be fixed. And so it felt a little in haste and they weren't part of a collaborating with a solution for it. So I'm like, Hey, this is broken, but I also have a few ideas and I can help and I have time to do it. I'm not distracted by calls and deals and all that stuff.
Todd Bustler (04:05):
So I imagine you prioritized, you figured out, all right, let me unblock some stuff really quickly, get everyone happy with what's happening. Then there's prioritization of what to tackle next. How did it scale from there? How did enablement scale from there? Yeah, you eventually build a team. You have to prioritize different things on a per monthly sprint or quarters. How'd you go about it?
John Ley (04:26):
The first thing that I'd say, I know we've talked about this, what's not working if you are the first-of-its-kind enablement profession, if I was joining Shopify today, I would really make sure that Shopify has their sales process, well-documented stages, exit criteria, entry criteria. Everyone needs to be really aligned. It sounds super cliche, but if you don't do that well, then you have shit conversion data. You can't do anything effectiveness related. So I can't fast forward a year from now and run programs and be able to tell you why I shortened a deal cycle or I improved conversion rates or I improved a competitive conversion rate. We weren't even capturing competitive. So I think the deal architecture and Salesforce is first thing that you have to do. It's really boring grunt work and it's operational, but where you can get kicked out of the adults table really quickly on the enablement profession is if you can't show your own reporting and what impact what sort of KPI you're actually trying to influence. So if the systems aren't designed and I'm like, oh, I'm doing this competitive training, but I have no way to measure how often this competitor's coming up or if it's working, you get relegated pretty quickly. So I would say being more in charge of the data points that you want to influence is priority number one.
Todd Bustler (05:44):
What roles did you end up or functions didn't you end up working with the most? You mentioned compliance and risk and finance team. Then earlier before we hit record, you were talking about the ICP, which is combination of traveling, sales and marketing. What ended up being some of the projects that move the needle and what teams did you find yourself maybe working with more than you expected going in?
John Ley (06:06):
Yeah, at Square I worked, the traditional answer is on enablement and product marketing work really closely together and that's true, but I worked a lot with the teams that helped with throughput a lot more than I thought. And so I'm calling out the finance team, calling out the Salesforce development team. I'm calling out our operational partners. We're a financial services company that you can get started without a contract, but we need to make sure we do KYC, we assess risk, you got to go through legal finance. And so I generally found that you can make pretty people a lot happier by just increasing throughput. So that was a surprise for me. I had never worked with any of those teams when I was at Square.
Todd Bustler (06:49):
It's interesting, I think a lot of people think about enablement is like hardcore role plays and specific objection and handling. It's look, if you can just unblock a lot of shit our best people are dealing with, there's a lot of alpha there.
John Ley (07:01):
Yeah, a hundred percent.
Todd Bustler (07:02):
A hundred percent.
John Ley (07:03):
We were talking Johnny right before we hit record on ICP and you mentioned some costly or difficult learnings you had at your time at Square. I want to hear about them and then how you use some of those learnings because at Brex at least feels from the outside at different points in your journey. You've changed that ICP like, Hey, we're not going to work with these companies that we originally targeted and now you're moving up market. So I'd love to hear your kind of evolution of the understanding of the ICP and some traps for people to avoid.
John Ley (07:33):
Yeah, a hundred percent. There was a very brief stint when I was at Square leading the sales development team and at the time the program kickoff, it's like a numbers game. It's like how many leads, how many calls? You're building a capacity model more so than you're building a sort of a customer strategy. So you're building a lot of the capacity models. And so a lot of these assumptions that we made around leads, we would get these huge lists. We would get these big lists from Dun & Bradstreet or ZoomInfo or whatever it is, and even think about something as simple as I want to look at the mix code for restaurants. And for that you'd get a really, really wide spectrum. That could be anything from a McDonald's location to a fancy French bistro to an ice cream parlor in the middle of nowhere.
(08:21):
Those are all technically restaurants. And so what we really wanted to make sure wasn't going to happen is filling the top of the funnel with just a bunch of leads that aren't valuable for sales at all. And so I'm calling that ICP, but that's generally a good starting point. You and I before we started recording or we're also talking about who's in charge of ICPs at organizations. Is it marketing, is it data science, is it rev ops? I've seen so many brilliant data scientists try to nail the ICP and it never really works. I think function that knows the ICP the best are the sales reps that have been at organizations for at least two years. They've seen deals that they've gotten to the end where the customer wanted to join but then ran into this roadblock or they've seen, oh shit, never thought that would be a really good use case, and they end up finding sort of a pocket of customers that end up doing really well, so.
Todd Bustler (09:21):
It seems like a maybe superpower you have or just something you don't realize you're doing that a lot of people may not. It's just, let me go direct to the source on some of this stuff, get some real feedback, do a good job synthesizing it, and then get the right people in the room to make the right decisions. Is that right?
John Ley (09:39):
That's right. At the end of the day, that's as simple as that is let me interview about four or five people and I'm really good at distilling it in, organizing it in a way that people could digest on one page. But yeah, sometimes, yeah, that's how I think about the work.
Todd Bustler (09:56):
I love it. John, I saw you said customer feedback, not just some internal opinions or thoughts shaped some of Brex’s biggest wins. And I'm curious how you started to, because Brex, when they launched, I know I listened to a lot of Sam blonde stuff and really creative on getting into deals, but then scaled really quickly. So what involvement did you play in the outbound process? What was that journey look like and what were some of your learnings there?
John Ley (10:21):
Yeah, so I would say a lot of the Sam blonde stories around, he thought very creatively, I'm trying to leave a mark for early customers. And so Brex was a corporate card. We were startup, we were making cards for startups and we knew, right, we talk about ICPs, we knew if you were a venture backed startup that you've raised, you probably have these challenges that we had or a lot of founders had. And so we would go out of our way to do things like the deliver a fancy bottle of champagne during a fundraise. We would write, we call them grad cards for any company that would successfully go through their next round of fundraising and there'd be cards for the company and everybody, it'd be in the office in San Francisco and everybody would write their name on it. So it was like we would know when startups would attend to a conference, and there's a kind of a famous folklore at Brex where Larissa Rocha at Brex figured out where these at attendants would be staying at their hotel and personalized a Brex card and got the hotel staff to slip it under their door.
(11:22):
So I think the point of the story is if you are so certain that your product is going to be a really good fit, it's not just a SDR sequence. Let me call and email a few times and I recycle it back into the account pool once I'm done. It's a no. You should pull out every trick in the book because we're so certain that it's going to be a really good fit if we get 'em on the phone.
Todd Bustler (11:43):
Yeah, I love that. It's like the unscalable stuff right now works really well and it's also because a lot of people won't do that, but I think you make a good point in that it comes from the conviction that this person is such a good fit that makes it worth your time as someone to do that, not just like, Hey, I'm willing to do it. It really comes from the conviction.
John Ley (12:03):
That's right. That's right.
Todd Bustler (12:04):
Talk to me, Johnny, about some of the onboarding from the rep perspective. I mean this from a, I'm sure you've figured out over time what this rep profile looks like and how you've done enablement at the manager level on figuring out, Hey, how do I help these people recruit? How do I figure out what that profile looks like? And even through the onboarding thing we were talking before you hit record when you said, do we actually enable these teams to go sit with people in customer success and understand how they're really using our product? So I know there's two big parts there. Take it any way you want. Were you involved much in the hiring profile, who to hire? What did we learn? Not so much.
John Ley (12:41):
Not really. I know you started asking. Not really. I let managers do that for the most part.
Todd Bustler (12:47):
And then on the second part, did you build out training certifications first 90 days? How did the process at Brex get improved over time in terms of onboarding new reps? It's a big thing people are talking about, especially as they're trying to get more efficient and reduce ramp times. What were any of the big step function improvements you've found or big learnings on that front?
John Ley (13:10):
Yeah, it's a good question. I think there's four buckets of content that could be incorporated with a new hire program. There's some sort of async learning where reading materials you can have, there's some category of live trainings. I'm going to get in a room, show you a slide deck, hope you remember the information on the job learnings where you now are practicing and shadowing your peers and that, and then there's what I'll call a certification. So we're going to put you through some sort of exercise. It could be a call recording that you've already had with the customer, but it's a certification. We're going to make sure that you can nail one thing. I think a lot of people, as we've gone remote, have really gravitated towards the async and slide decks, so let's put as much as we can in the cloud so we can scale.
John Ley (13:53):
The problem is those all really suck, like AEs sit through these videos or maybe they don't sit through their videos, nothing gets retained, and so it's just kind of this catch 22 where more of the sort of real life simulation on the job is the important part, but it's tough to scale, but we do it anyway. So we make a point to have a certification process that reflects an actual sales deal. So our certification is step one, first week, can you target the right person? What are you saying? Why are you reaching out to them? What does a personalized phone call and a personalized email look like? They email that to me. They call my cell phone, so they have to call my cell phone. I decline it three or four times and make them actually try to target me. That's the step one. Step two is a discovery call where we have a rubric and you get on the phone with us.
John Ley (14:40):
Step three is how do you involve your solutions consultants to give a tailored demo? Step four is deliver a high impact proposal and try to wrap up a deal with a couple personas. So we'll put an economic buyer and the champion in the same room. Everyone's got their ready positions, and so we do those four things. We're like, if you can do those four things over the course of the first couple months, we think you're on a pretty good path moving forward. So I don't know, where do people struggle the most in those four parts. Discovery.
Todd Bustler (15:06):
Any part of it in particular? Just not going deep enough or any specific area.
John Ley (15:11):
I think one thing that we've really learned is the importance of use cases with your product. There's a big LinkedIn debate over the last couple of years that it's problems are more important than product, which I generally agree with. But I would say to further that argument, I would say product use cases and how people consume it is way more important than product capabilities. So you definitely need to know your product. I would say it's hard to do really good discovery if you're not fluent with your company's use cases. What were customers using before? What was painful? What got unlocked when they joined your company? And now tell me about five different types of verticals. That's true in, so you have to be a bit of a chameleon on discovery calls. And so now we've brought in a lot more shadowing our CSM or actually getting on the phone with customers that have been around for a year to understand what they like about Brex, what it was like before joining Brex. I really think deepening the understanding of your customer portfolio helps with better discovery.
Todd Bustler (16:20):
I agree on the use case. This part, I like that, like you said, it's either focus on the problems or focus on the product, and it's actually in the middle there where it's like the before and after is what being used, how your product enables a specific use case or business process or something to be improved. Who helps in that onboarding it, whether it's four weeks or four different process. Is this all your enablement organization? Do you have sales leaders and even high flying ics getting involved in certain components of this? Because a common pushback I hear from sales leadership is, look, I don't have the time to do this. Who's responsible for this? How have you guys scale that?
John Ley (16:58):
Yeah, no, that happens all the time. And the short answer is yes, we do rely on a bench to help us. I would say there's a combination of sales. So if you're a sales manager, you always like one 30 minute slot a month. If you can't afford one 30 minute slot a month. The size that we're at that works for us generally with when ICs and sales reps get asked to join, it's part of a team lead position that they're in or they volunteered to be a sidekick part of their management track, and so that's where I think the relationship with your people team is generally helpful is identifying that there are specific responsibilities depending on what sort of track you're on. But yeah, I would say enablement teaches a third leadership and sales reps teach a third, and then I would say XFN partners teach a third. It's nearly impossible for one person to be a subject matter expert on everything that just won't work.
Todd Bustler (17:53):
Yeah, that makes sense. You have to split up. The last part I want to dig into here. One thing that I think has really changed in the last 10 years of software sales is the markets are changing so quickly. We all hear about all these AI oriented companies that can develop product way faster. I'm sure you're seeing it at Brex, we're seeing it at Shopify, changes the competitive landscape. There's new features that you have to continue to enable people. Have you changed the frequency and cadence on how you do competitive education or product updates because it is faster than ever and I wonder how people are approaching it at a larger scale.
John Ley (18:32):
Yeah, no, it's a really good question. I think back on as somebody that's owned competitive programming, I think back on where I would spend a lot of my energy just a couple years ago and I have a library of decks and I would break down, you go to a website and it's a bunch of, oh, here's all the green checks that we have and all the red Xs that they have. Sales does not want that. Sales wants shooting straight. Why am I going to maybe lose this deal? So I had a lot of very practical, this is where we're getting crushed. This is where we're actually really crushing them. So this is how you do that. And I have to do that on a number of different competitors and now I'm spending a lot of my energy on working with internal engineers to develop a chat bot.
(19:16):
So I'm like, what's the point of making 50 decks when I can just start referencing internal documentations or help centers or external resources and I can just query that. So it's like imagine I'm an SDR that doesn't have that much context. I'm reaching out to this controller and I want to give them an objective stance on these two comparisons. Where we're putting a lot of our energy is with tooling with the engineering team. So now I can just start querying where do we beat and where do we lose a certain competitor? And we think that if you federate that to all the employees as opposed to a series of decks, then how could that not be the competitive program?
Todd Bustler (19:57):
A hundred percent. That's it. That's definitely it. I think we're going to laugh in maybe months. Oh, we're going to once every two weeks or once a month, we just pick to do that. Why wouldn't you just ask this thing? Or a bot's going to get updated based on calls that we're having. That's definitely the way it's going to go. What advice do you have, John being in your position for? I think a lot of people that listen to this are first time VP of sales or first time CRO and trying to learn from a lot of their peers. I think if you're that first time sales leader hiring enablement for the first time, what advice would you have for those people?
John Ley (20:32):
So CROs that are looking for a first time enablement hire, I would recommend you do three things. One is find somebody that has a sales background that wasn't a sales reject. That can be hard to do, right? That can harder. That narrows the pool, but that's a really important part, especially if this is a first-of-a-kind enablement hire. If you miss that, somebody can get laughed out of the room, not taken very seriously. You want somebody that's been sales manager, sales rep, wasn't a reject, did pretty good, had an opportunity to get promoted into enablement. That's kind of what you're looking for and hopefully you can find that person. The second thing that you want is somebody that can, there's two things this person's going to need to do. One is make trainings that don't suck. So they have to be interesting, have a point of view on something.
John Ley (21:21):
They can collaborate with their peers really easily, make trainings that don't suck. The third thing that they need to do is present a strategy on how they want to build enablement. That could be like, what's the enablement service model? How do I intake people's ideas and prioritize? What would I do with the second enablement hire? What would I do with the third? Enable? You need somebody that can cut together a basic plan. So it's those three things. Vet for one, practical sales experience, somebody that's trusted. Two build trainings that don't suck so people take you seriously. That's your field validation with the field. Three is, can you put together how you would grow an enablement team as we grow over time?
Todd Bustler (22:04):
I like that third part as a way to like, okay, there's always shit that's broken, right? There's always some IC or manager saying, why don't we have this? How do we make this better? And you need some way to go about that. I agree with that first part too. I think I've worked at organizations where people would sit there and see a sales enablement leader and you could just tell there's no listening happening here. Who is delivering the messages whether we like it or not important?
John Ley (22:32):
Yeah, I agree. And teams get bigger, and sometimes people have this content specialization. That's not a blank statement, but I'm talking about if you're really trying to find somebody to anchor the team around, like a pillar for the team, those would be the three things I wouldn't compromise on.
Todd Bustler (22:47):
Love it. Johnny, this was awesome. Appreciate it. I thank you for your time. Congrats on the run you had at Brex. I appreciate you taking some time to sit it down with me.
John Ley (22:56):
Todd, thank you so much for having me.
Todd Bustler (22:59):
Thanks for listening to Cracking Outbound. If this was helpful, let us know by messaging me Todd Bustler on LinkedIn and share this episode with a friend that you think will be interested. If you want more resources about building and scaling all things outbound, you can sign up for our newsletter at champify.io/blog.