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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.
Ryan Heinig (00:00):
The best advice I would give to an AE that is focusing on prospecting every day is go see coaching. RDs, especially the bad ones, and there's tons of bad ones out there, they want to go focus on the number one deal in their pipeline and they want to go be a part of that. And if you aren't the AE that has that number one deal, you're going to get less attention. And the best AEs in the world, they go seek coaching, they go to another RD outside of their direct leader, they go to a rep that is absolutely crushing it.
Todd Busler (00:31):
Everyone wants to build stronger pipeline, but only a few know how to make it happen. If you're listening to this show, you know 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 Busler 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.
(00:58):
I'm really excited to have Ryan Heinig join the show today. After a great run at leading companies like Qlik, AppDynamics and VP of Americas at ThoughtSpot, he made the jump to be the CRO at Philadelphia-based 2X Marketing, a marketing services business backed by Insight. He explains why he made this move, how he evaluated the opportunity and how you should evaluate future opportunities and why his team says he's empathetic but firm. You'll notice his ability to get strategic but also stay really close to the details. I think he's one of the best CROs in the game right now and there's a lot to learn from this episode. Enjoy.
(01:33):
Ryan, thanks for joining me. How are you doing?
Ryan Heinig (01:35):
Good, man. How are you doing? Good to see you again.
Todd Busler (01:37):
I'm doing great. Friday morning. Feeling good. Excited to chat with you every time we talk, I learn a lot and I know based on the prep here, there's going to be a lot of good stuff here, so I appreciate you taking the time. Your run to CRO at 2X has been really impressive from learning under some of, I think, the best leaders in all of B2B SaaS and sales in general, and some of the hottest companies from Brian McCarthy and the ThoughtSpot guys, AppDynamics, and now doing it at 2X with a company I know just got a really big investment. 2X. A little bit untraditional. What drew you to them? How'd you think about this opportunity?
Ryan Heinig (02:14):
Yeah, no, a hundred percent, you're right. I definitely learned from some of the best and it's helped my career. Learning is critical. I always tell people, get a mentor. That's the best thing you can do. And you're right, 2X is totally unconventional. Matter of fact, a lot of my software friends probably call me once a month and ask me how my midlife crisis is going. It's not a midlife crisis, just so I let everyone know what's the number one thing that you want to look for whenever you're selling any solution, whether it's software or you're selling chairs, is there real pain in the marketplace and does my solution uniquely solve that pain? And I have to say that a 2X has the most pain in the marketplace as compared to any solution I've ever sold. What really drew me to it was I saw it happening firsthand at ThoughtSpot. I was sitting in the boardroom right next to Scott Holden, our CMO, and watching his budget get cut by 30%, but still having his revenue and his pipeline numbers exactly the same. Every marketer is being faced with this challenge. And if you don't think about your marketing org differently, you're going to struggle. CMOs have the lowest tenure, 18 months is the average tenure of A CMO. So I was really drawn to that and that's what caused me to join 2X.
Todd Busler (03:18):
Before we get into all the details of how you make the revenue orgs hum and what you've learned and what you've carried over and what you had to change, how do you go and vet that opportunity, right? Because sure, you saw this and you're like, okay, there's something here that caught your interest, but it is a little different. How'd you go test for that poll?
Ryan Heinig (03:36):
Yeah, I did a couple things. One for me, leadership's critical, especially as you're in senior roles. So I really fell in love with the CEO. I think Dominic, our CO is one of the most talented individuals I've ever met with both from a intelligence perspective, but also his ability to get things done. It's pretty amazing what he's done at 2X to get us to the point at which we're at. And then two is you have to go test your network. So I called a bunch of CMOs, I said, hey, if I was selling this, is this something that you'd be interested? Do you really have this pain? Are you struggling with this? Would you be open to a model like this? I did the same thing when I went to ThoughtSpot. I called a bunch of the BI directors that I sold to in the past and said, would you be interested in this? Use your network. And that's something we'll probably talk about throughout today is always building that brand that you have a strong network of people that you can call on and ask a favor, I think is critical to the industry that we're in.
Todd Busler (04:24):
Love it. What's it like selling a tech enabled services versus traditional SaaS, right? You spent a decade doing very traditional kind of pay per seat normal models, and now this is clipping on its head. I think you've been early on a trend and I feel like a lot of people are moving more to this services oriented model, but what's the biggest differences been?
Ryan Heinig (04:46):
And you're a hundred percent right, and any enterprise software seller, we think we're the best in the world. So I obviously came in expecting and assuming I knew everything and that everything would be easy. The good news is that about 95% of it is the same. I'm a true believer that the best sellers in the world do four things. They PG, they do great discovery, they do great qualification, and they're amazing at champion building. And once you know it, the best reps at 2X do those four things amazing. Their pipeline's always full. They're always getting to the real pain and not the surface level pain. They're qualifying deals and only spending time on the deals that matter, and they have the best champions in the world. Their champions want the deal as much as the rep does, and that is all the same. No difference there whatsoever.
(05:29):
The only two things that are a little bit different in our world, you really have to do great discovery. You have to do great discovery everywhere, but we can solve a hundred different problems for a CMO. And if you really just attack that surface level pain and not really dig into it, you're either going to do a small deal or you're going to lose to no decision. So we spend a lot of time on that. We do a lot of skill development around great discovery. And then second piece is authenticity. And what I mean by that is I've seen sellers in the software world win because their product's the best. And when you're selling services, you're selling people, you're selling you. You truly have to be authentic, the person has to trust you. So we do a lot of time around that too and making sure our reps really come across representing the brand and representing their authentic self.
Todd Busler (06:13):
Has it been challenging, Ryan to get people with traditional SaaS background that are more like, hey, this is exactly what our solution solves for the two or three use cases? Yes, you have to hunt to find them and build champions, but it's more straight and narrow where this feels like you have to get in there and understand someone's whole entire go to market process. And of the a hundred things you could potentially help with, what one am I going to narrow in and has it been hard to teach people that?
Ryan Heinig (06:39):
Yes and no. If you look at the AppD playbook, which again, I think is the best playbook in the world, what do they hire for? They hire for ice intelligence, coachability character and experience. They also talk about curiosity a lot. So a lot of times that discovery is just intellectual curiosity, and we have had a few reps that have struggled that are used to solving one problem. That's why we've had a lot of success hiring from analytics. As analytics solves a hundred different pains in the marketplace, what you sell, you can talk to a bunch of different buyers. So someone that hasn't sold just a singular point solution is sold to multiple buying personas has come here and they may able to flip that. But again, from a hiring perspective, I think something that's critical is you have to hire people that are willing to learn. The world is changing so quickly, and if you don't have someone in your team that really wants to learn, and in our world, marketing's not that difficult. It's not like software engineering where I'll never understand software engineering. If I spend enough time, I can understand marketing and our reps that really understand marketing and want to learn. And I think that applies in anything that you sell. They do the best. They really show up for their client and their client really trust them.
Todd Busler (07:47):
I think that people that have sold analytics, which yeah, that's a category, but it ends up being broad. You're tying to a bunch of different use case those reps are trained to, okay, go and find these different business problems. I think it's very hard to sell in that category too. Always so many players in the differentiation is not that high. I have a rule. No more charts, not semi chart, no more charts. You have a reputation, Ryan, every time we've been at Champ five for about three years, every time I post something about you or you give us some content or some nuggets that I share, I get a bunch of dms people saying, oh, I loved working with him. I learned so much. That's awesome. You shared that I think you have this reputation for being very people driven, but also very firm and performance driven. What's your philosophy on scaling the sales culture alongside pipeline and everything that goes with it?
Ryan Heinig (08:38):
Yeah, if you asked me that question three weeks ago, I don't know if I would've had a good answer, but I was talking to a rep that used to work for me the other day, and as we hung up the phone, she said, okay, I'm going to go chatter my inner Ryan. And obviously I was like, what the heck does that mean? And she was empathetic but firm and I was like, huh, that's a good way of putting it. I think too many sales leaders can go one way or the other. So for us, culture is like we have a lot of fun, but there's high expectations. We realize we're at a special company, we realize that we have a comp plan that you can make life-changing money. You don't pass up those opportunities. Culture is we treat people like adults. People don't want to be micromanaged, but they want to be successful.
(09:15):
You have your kid's baseball game, your dog's sick, no problem, go do it. But when a client raises their hand or a deal is coming across the finish line, the expectation is that you'll be there. So I think the balance between being empathetic, letting people have fun, having an environment where people can try new things and not be afraid of failure, but being very firm that I expect high expectations. We tell people in the interview process like, hey, if you want a 40 hour work week, don't come here. There's easier places to go, make your base salary and a little bit of your variable, but if you want to do something special, a, you'll have a lot of fun. You'll learn a lot, and the expectations are going to be high. We think we have an incredible opportunity in front of us and we want to go get that.
Todd Busler (09:57):
When you were starting, I think more of the firm fear-based leadership, I would say on the stronger end of that was more popular. What's it been like taking maybe people earlier in their career where just philosophically and culturally, I think this has changed quite a bit. Any advice for people trying to walk that balance between firm but also, hey, we're having fun. I'm giving you a big opportunity here.
Ryan Heinig (10:25):
Yeah, yeah. Well one, I agree with you a hundred percent. It's a hundred percent change. I've even seen the leaders that fear-based leader, they've changed and they have changed their talk track a little bit and it's good to see because honestly, I think the empathetic affirm is the right way to do it. For me, and I struggled with this in the beginning of my career, you want to be everyone's best friend. You always want to give him good news. I think you have to be very direct in your expectations. We talk about it a lot like, hey, if we have an opportunity to review and we decide on an action, you have two choices. You can think about it and realize that you don't really want to take that action and then come back to me and we can have another discussion or obviously go do the action.
(11:05):
But outside of those two things, you not doing that action is unacceptable. And there's certain things that I really will now home. If we decide to do something and that doesn't get done, I'll make a big deal out of it. We have to understand that our time is valuable, and if we put together four or five people in a room and do an opportunity review and at the end of the day it fails at the last mile, the rep executing that action, that's unacceptable. As a leader, I think there's certain things you have to not let slide, and that's critical.
Todd Busler (11:32):
I want to dig into that, Ryan, because I think a lot of leaders, I know I was guilty of this earlier in my career, it's relatively easy to say, here's the expectation, here's what you need to do. It's a lot harder when that doesn't go well to say, okay, what do you do when someone's not meeting those expectations? What does that conversation look like? You've done this hundreds of times. What have you learned there? What's good look like?
Ryan Heinig (11:54):
Yeah, one, I think it starts with winning the hearts and minds first. And that's something I talk about with every single one of my leaders and every leader that I've ever had. If the person understands that you have their best interest at heart, difficult conversations are easier. I fired people that at the end of the day, they didn't want to get fired, but they knew that I was doing it in the right manner and I always had their best expectations at heart. So to answer your question directly, I think you have to lead with data. You can't let it get emotional. You can't let it be like, hey, I think this or I feel this. You really have to start with data. And then I think you can flow into the more qualitative hearts of, hey, it just doesn't seem like you're getting this. Let's talk about it. And you have to prepare for those conversations. Too many leaders just run into those conversations. If I'm going to go have one of those conversations, I'm going to block the half hour before that. I'm going to make sure the words that come out of my mouth are the right words because in those conversations you say the wrong word and really can go the wrong way. And it's really important to be crisp in those conversations.
Todd Busler (12:52):
That's great advice. You see people like, hey, you have a massive sales meeting come up. Sure, everyone's going to prep for it. But that internal conversation, those coaching moments, you only have so many of them and they matter. And the words matter a ton. I think that's great advice that people maybe under prepare for or don't realize how important it is.
Ryan Heinig (13:11):
And that's where you win somebody for the future. That person will work with you forever. You have that a player and you've turned them into even a better person because you've changed them a little bit. People want to be coached, especially in this industry, no one comes into software sales or services sales wanting to be average. They want to be great, and if you as a leader aren't helping them get there, they're going to go find someone that does.
Todd Busler (13:37):
A hundred percent. Ryan, you've led it done as an IC and then led at every level. Now AE frontline leader, second line leader, VP of Americas, CRO, how's your view on, you mentioned those four critical parts to be successful, PG pipeline, Jen is a critical part of that. Obviously you named it first. How has your view on outbound evolved with each step up?
Ryan Heinig (14:03):
Yeah, I think there's obviously different things you have to focus on when you're at different levels. One, when you're the AE, you're the one doing it, right? And I think the best advice I would give to an AE that is focusing on prospecting every day is go see coaching, right? RDs, especially the bad ones, and there's tons of bad ones out there. They want to go focus on the number one deal in their pipeline and they want to go be a part of that. And if you aren't the AE that has that number one deal, you're going to get less attention. And the best AEs in the world, they go seek coaching, they go to another RD outside of their direct leader, they go to a rep that is absolutely crushing it. If you're an AE, schedule a meeting with other people and ask for advice.
(14:42):
You'll never have more time on your calendar than when you're an AE. Go use that time and go get better. Then you move to an RD, right? And now your job is to enable your team. And one of the things I used to focus on a lot when I was an RD is like, how can I do one thing myself that then helps the eight reps on my team? I used to spend time writing the email. If we get an event coming up, I would write the email and then if I knew I put that half hour in, that would save my reps a half hour times eight, and the email might be better than what the reps write so they have a better chance of being successful. Go spend time with your field marketer and make sure that the event coming up is the right event or just schedule the one-on-one and just say like, hey, we're going to go after AmerisourceBergen.
(15:24):
I'm just going to sit here and watch you break down this account. And I'm not going to say anything until there's something that I would maybe do differently. So the rep is about to write the PG email and they don't mention that the person that they're going after came from SAP and SAP is our number one client. Don't you want to coach your rep to do that? But you can't do that unless you're in the moment. So RD is really all about enabling your team and then usually move to a second and third line leader. I think the number one thing is again, the firm expectations. So if you're going to run a Monday morning meeting, a PG meeting, your job as the VP is not, get lazy and show up for that meeting every once in a while. Make sure that your reps know that it's important there. Make sure that your RD knows that it's important. The PG mindset doesn't change even when you're the CRO. It has to always be there and be a fabric of the culture.
Todd Busler (16:09):
There's so much cold there. And for people listening, RD, regional director, frontline leader, I like that you sit down and do that with them and observe just like, look, I'm going to watch you do this and I'll tell you after what could be done differently. But there's little nuggets that people that have been doing this for a while think are second nature that aren't right. And you have to be taught that. And the best people are getting into the weeds and teaching.
Ryan Heinig (16:35):
It might be a tactic or it might just be like, hey, by the way, that person you brought about to go after, I've sold to six times in the past. Yeah,
Todd Busler (16:40):
I can text them. Hang on, there's an easier way to do this.
Ryan Heinig (16:44):
No, and again, that's where you win the hearts and minds of your rep is when you really lean in like that and help them out.
Todd Busler (16:50):
I think one thing that's also interesting about your background is there's some people that have nailed commercial and S and B. There's some people that are like, look, I've only been in Strat where I have five accounts my whole life. You've seen the gamut and the motion changes dramatically across that. When I say that, I mean commercial at enterprise to majors. How do you keep the PG motion consistent when the tactics look very different across those different segments?
Ryan Heinig (17:19):
Yeah, that's a good question. And they're totally different. And I have, I've been an enterprise rep and then I ran commercial and then I went back to enterprise and then I ended up taking over commercial. So I bounced around a lot. They're very different. So commercial, right? You have a bunch of early people in your career. You say jump, they're going to jump, right? You say PG, they're going to go PG. The main thing there is coaching and enablement. So that's where you're doing more of those one-on-one meetings, making sure the messaging are tight, asking the B, c you on the emails, there's going to be a ton of effort there and ton of action, a ton of outbound. You want to make sure that it's quality going out. Then you move up into enterprise and majors and these are the reps that they've already done it, right?
(17:55):
They know everything. And that's where I think the cadences are critical. It has to be part of the business. So do I have that Monday morning meeting? Is there an expectation that you are consistently hitting the leading indicators? We have to do a good job if that rep is the number one rep in Q1, make it about them and say, hey, I know you're the number one rep in Q1, but I'm looking out for your Q2. So one thing that we did, a ThoughtSpot that really helped here, again, RDS first line leaders are the most important role in your company. They have to be the best in the world. We would have a pipeline forecast meeting with the RDs. So every single time we did that, we had RDS that were consistently the number one and number two RDs in the company. They show up to the pipeline forecast call, and they're the worst from leading indicators and they don't want to be the worst at anything. And you have to have that accountability. And what they would do is to get off that call, they would be a little uncomfortable and they would go drive pipeline within their team. So it has to happen at every level, has to do it differently at every level, and you just kind of got to figure out what works.
Todd Busler (18:56):
Yeah. Two big takeaway for me there is like there's no one size fits all there. Cadence matters, but the cadence is going to look differently and how do you use that cadence? And for people listening when Ryan's saying Cadence, this is an operating cadence, the series of meetings that you're having leading out to the results. Yeah, some good points there. How do you think about the key indicators for outbound? Are we on track? Are people just doing busy? Are people just doing mindless activity? How do you think about it?
Ryan Heinig (19:25):
Yeah, I think it's critically important to not look at any leading indicator in a vacuum. So a lot of times people are just like M zeros or discovery calls and they can be busy work because the threshold to hit a discovery call or M zeros almost nothing. One of the best things we did at ThoughtSpot is we changed the focus from the number of M ones or M zeros, excuse me, that we were setting to S twos, which was at the POC stage. Because at the end of the day, if the M zero is a quality M zero, it's going to go to M zero to M1 to S one and S two. So you really have to measure the full kind of early sales stages and make sure that all the leading indicators are being hit. If they're not, you are just doing busy work.
(20:07):
And then to your point, you asked an earlier question, that's what allows you to coach. So you have that rep that is setting 3M zeros a quarter, which is way less than they should, but all three are converting. They're going after the right ICP, they're going after the right buyer, they have the right messaging. Now my message to that rep is, hey, you're doing all the right things. You're not doing enough. How do we help you? How do we maybe get you involved with some partners or how do we get you another account that you can get after because you got all that stuff tight? Or you have the rep earlier in their career that's doing 27 M zeros and none of them are converting. It's like, look, you're just looking for a yes in an email. Let's slow this down a little bit and make sure we're going after the right people. So that's where the leading indicators help you be a better leader. And then again, go win that heart and minds helping that rep get out of something that they don't even know how to get out of.
Todd Busler (20:55):
There's a lot of gold there, Ryan, right now I think selling, whether it's SaaS or services, the markets are changing so quickly from like, hey, we value prop where you had an interesting kind of unique or comparative differentiator. They're going away very fast or new AI entrants are coming into the market. I talk to a lot of sales leaders that are saying, hey, I'm putting a lot of effort in PG, I'm getting people to get into meetings with the right accounts, but we're actually seeing our conversion to a visible opportunity or to A POC or whatever. You look at that middle level of success drop dramatically. Do you have any examples of where you've seen a big change like meeting top opportunity conversion drop, and how do you dissect that? How do you figure out the root cause? How do you get to the answer? How do you act on it?
Ryan Heinig (21:47):
Yeah, it's real. We're seeing it in all the businesses. To me, the difference between the opportunity moving throughout the sales cycle is your champion. So we recently this year we saw this happening and we rolled out the value framework, which everyone's familiar with, current state, where we go from there and we made it mandatory early in the sales cycle and we made it mandatory that you develop that with your champion. At the end of the day, a lot of the deals die when you're not in the room. They die. When the champion's really excited about something, they knock on their VP's door and the VP C says, get out of here. And that's your champion doesn't know how to sell better than your champion knows how to sell. So if we're not enabling our champions with, hey, you're going to get the question, what is the current state and why are we even talking about this?
(22:29):
What is the desired state? Where do you want to take this? Okay, so I'm kind of listening to you about this piece of software or the services that you want to buy, but really what are the required capabilities that go make this happen? And then obviously the most important question, this is where 80% of champions fail is like what are the positive business outcomes if I let you buy this that make that happen? So we develop that framework with our champion and then our champion uses that slide. So we create those pieces of collateral and if you look across a lot of the enterprise software companies, the best ones in the world are doing that and it's mandatory and it really, again, too many people look at that as an internal checkbox that make their SVP of revenue feel happy. It's not for that. It's for your champion to use it externally. They don't sell software. They're not used to selling software, but they have to do it.
Todd Busler (23:17):
Has there been much differences selling services, tech enabled services versus pure SaaS when it comes to things like required capabilities and PBO and for people, PBO is positive business outcome.
Ryan Heinig (23:29):
The required capabilities definitely has changed because when you're selling tech, there's going to be technical requirements that you either do or you don't and they're going to flush you out of that. So our required capabilities list often is less than what it was like in software, but the PPOs are just as critical. People want to know, hey, if I go buy 10 FTEs from 2X and I change the way that I'm going to do marketing, what are the positive business outcomes that are going to happen from there? Our customers hold us accountable. Did I get more awareness? Did I drive more pipeline? Is my revenue converting? Am I moving through stages better? They're all the type of things that we allow to do in a better economic way, and we want our clients to hold us accountable to that. If we're not making an impact, then you shouldn't retain us as your service provider.
Todd Busler (24:14):
It's nice though, what you're selling right now in this environment, just because this such clear, here's cost savings, here's exactly what it's going to be, here's the alternative, which I think the people selling sexy SaaS, ai, whatever it is, it's like cool, if you're on time savings today in 2025, you're in trouble getting that attention. So it's a nice opportunity you have in the early days. Ryan, if we go back to getting going at Qlik in the BI space or AppDynamics, what were some of the hard lessons you learned when it comes to outbound? I think a lot of these early learnings shape a lot of your thinking. So what have you learned in those earlier days?
Ryan Heinig (24:53):
So I think what I've learned is you have to stick out from the crowd, and that was important back in the day. But now with sequences and every buyer just being slammed with messages 24 7, I know I see it myself. You can very clearly tell when it's a sequence, you have to spend the time. I'm a big believer in the veto letter. What's veto Ryan? Very important top officer. I think it is. Google me on that, but I think I got it. So if I'm going to go after the right person, I have to be able to stick out. So Google around, use Facebook, use LinkedIn, check their podcast, see something that we use a lot. Is the person a chief member? Are they part of CMO huddles, people like being in their community and our CMO presents in CMO huddles or did they previously work at one of our top clients?
(25:43):
You have five seconds for someone to glance at an email and maybe read it. And if you don't do something differently, if you say increase pipeline by 30%, that's just a delete. I'm moving on from there. So messaging is key and it's even more critical today than it was. And then I've really kind of, and this is something that I've grown into in this new role, is the power of tools like six Sense going after people that are showing signs of buying your product solution or services. Leverage these platforms today because you want to be prospecting into people that are in market. Those people are going to be the people that take the meeting. So really leverage those type of tools, those intent tools, it's going to help a lot.
Todd Busler (26:24):
Both of those companies were and still are in super competitive categories. So a lot of the leadership at your competitors was running some flavor of the same playbook. What do you think led to the success there? Is it just better execution? Is it, you nailed the training part. Why do you think led to some of your success there or what did
Ryan Heinig (26:48):
I do? I mean, I think at Dynamics, again, I said it before and I'll always say this, is that I think they had the best playbook in the world. I do think our competitors were really good products and things like that. I think we led a better go to market. I think that we had the value framework now and we used the three whys at that point. I remember one of our abs showing me the presentation that his champion or our champion built, and he was like, you'll never guess what Eric built. And I was like, yeah, I will. I built that and gave it to him. So I think those things are critical. The other thing that we had both Qlik and AppDynamics and ThoughtSpot is there were set use cases, there were set budgets, there was a set problem in the market, people had budgets set aside for this and we just had to go be better. So I like being the disruptor and I think if you're looking at new opportunities, is there a budget set aside for solving the problem that my solution sells? If not, it's an evangelical sale and that's tough. So I think you really want to go focus on something. Are people used to buying something in this category and can I just go be the better solution?
Todd Busler (27:50):
Yeah, it's a lot easier when, hey, we're going to spend in this world. Tell me why you're the best one or tell me why it's with you. Then hey, go create budget. And I'm seeing that firsthand on the other side, and it's not easy. All of the champion building, it has to go to a level 10, right? Because not only is it why do we need to do something in this new category that most people haven't heard of? It's not the safer bet. It's hard. Where do you think most of these outbound teams, Ryan break down. A lot of people say, hey, we're going to go try this PG motion. I had a conversation with some CRO who has run it successfully. Where does it break down?
Ryan Heinig (28:27):
Two things is showing that it's successful inconsistency. So let's start with the first one. Every single time gets someone gets a meeting, maybe not every time they send it to me and I send it out to the team, PG sucks. It's hard, right? You're going to fail much more than you succeed. So you're in a slump and you see your colleague send a great email and get a meeting with A CMO at a great ICP account. Those are things that lift you up and then you also have to share it when that deal close wins. So you got to really celebrate, hey, this is sales proactive, right? 61% of our business last year was sales proactive. There are deals that don't exist if sales hasn't sent a LinkedIn or sent an email. And you really have to know those numbers and celebrate them when they happen. And the second part, we already talked about that consistency. So you're going to be busy or not busy and things are going to flow. You start getting lazy on the Monday meetings, the reps are going to get lazy. It has to be a fabric of your business, a PG culture, people always talk about the great software companies of today have that PG culture and it works because the reps with the most pipeline have the most success.
Todd Busler (29:27):
I think everyone's always looking for shortcuts and everything you're saying here, when you listen to it, you're like, this is relatively simple, very hard. But it's relatively simple equation. I think what separates people like you that from others that haven't been super successful is you're beating that consistency drum. You're constantly having those conversations that are slightly uncomfortable and that's required. There is no other way.
Ryan Heinig (29:54):
I had a mentor that used to always say is enterprise software sales is simple, not easy. It is super simple. You go back to the four things we talked about. These aren't rocket science, but it doesn't mean it's easy. Everyone's a little nuanced, the consistency. Another mentor used to say being a sales, like going to the gym. You can go to the gym every day and not look good, but you have to go put in the work. And if you do that, you'll be successful.
Todd Busler (30:16):
More tactical question here, Ryan, what's something you believe or you used to believe about outbound that now a decade later you don't believe?
Ryan Heinig (30:26):
Yeah, so I fell into this at Qlik. I did a lot of those veto type messaging and then when I was at AppD, it's all of the sequencing tools came out and I was like, this is great. Just plug and play and see what happens. And you get a couple early wins and you think that you found the cheat code. I am starting to move further and further away from sequences. There's still areas where it works. So we have a closed loss sequence that's very successful because it's super simple message and it's repeatable. But if you really want to break into a net new account, it has to be creative, it has to be unique. And too many reps just think, if I'm going to load up my sequence on Monday and let it ride, it just doesn't work. Buyers, they can tell what the sequence is and the number of responses that you're going to get are less and less as the years move on. So if it's not a special message, it's not going to get answered and you're wasting your time.
Todd Busler (31:12):
Anything else? I
Ryan Heinig (31:14):
Agree with you, but we don't really use them now. It's almost like why invest in an incredible tool like Champify? You have to go find that buyer. And if you miss that opportunity, when that buyer goes to a new organization, you miss your opportunity. You have to leverage those kind of tools or you have to leverage deep research. And I am a fan of leveraging AI there to help me pull out the nuggets to be unique. But if you don't just spraying and praying, it's not going to work.
Todd Busler (31:41):
It wouldn't be a podcast in 2025. Without talking some about ai, you just mentioned the deep research use case. Is there any other parts where you're seeing AI dramatically help your team?
Ryan Heinig (31:53):
I think it's that. I think it's the beginning of the prospecting cycle. I think we are starting to play around with the inbound motion like, hey, can AI really help nurture the people that aren't ready to go into the cycle? And I believe that either today or sometime soon, that's going to be really successful with that. But as far as outbound, there still needs to be human there. But I think there's a lot of ways that you can leverage AI in account research in getting to, we will use the value framework, we'll put that into the AI platform and say, hey, help me fill this out and then I will get an idea of my messaging before I go to it. So I do think that you're going to see more and more AI leveraged by sales executives.
Todd Busler (32:32):
Yeah, I think very similarly like that. I think there's some interesting use case of AI when you sell more s and b, more like super mature categories, more commoditized, hey, can I rip something out that I pay $5,000 for? But if you're selling super strategic to a small list of accounts, it helps with the research a ton. Don't get me wrong. You can find things that you never would've found or help put together stories a lot easier, but doesn't change the work you have to do. Or at least not yet, or I haven't seen it. When you stepped into the CRO role at 2X, a lot of people listening to this are stepping into their first leadership role or trying to vet an opportunity that they want to step into an early leadership role. What were the first changes you made? You came in, you did some understanding, you talked to some mentors to understand the pull in the market, then you got there, you always have an idea of what the company's doing well and not, and then you see it for a couple of weeks. What were the first changes you made? What were the big go-to-market priorities you tackled?
Ryan Heinig (33:30):
I say this all the time. I walked through a situation where I was incredibly lucky, still away from with her today, came into a situation where I had a sales leader name's Melissa, one of the more talented sales leaders I've ever worked with. So I was really able to point her on, hey, just continue to go run the business. Why focus on building the business? And then the other thing is throughout your interview process, if it's not super clear why they're hiring you, are you really needed for that role? So my CEO was like, hey, here's the things that we really need to focus on. So I came in and I made changes in areas where we needed to make changes. I coach anybody coming into a new org don't go making dramatic changes just to make them. So we focused first and foremost on sales stages.
(34:08):
There was three sales stages didn't align to the buyer's journey because there was three or four key actions that kind of were stuck in each sale stage. And then also the sales stage just didn't have very specific extra criteria. So it was more of like a discussion, are we in stage two or are we stage three? It's like, no, there needs to be a specific extra criteria and then you move to the next stage, which helped us really fix up our forecasting. And that was really my number one mission to come in here. I mean, if you think about it, forecasting our world is the most critical. It's way more critical than SaaS because if I sell a bunch of services and I don't have the people to deliver 'em, that's a poor customer experience or vice versa. If I have a ton of people sitting on the bench, my gross margins get smoked.
(34:48):
So we really focused on the specific stages, the specific sales categories. We focused on moving forecast to a math equation as opposed to just thinking about how we feel about the deal. And we focused on hiring, right? Hey, we're going to really build a ideal rep profile and then we're going to build a repeatable process. So we put every rep through that so we know the reps that we like and we don't like. And then finally, the last thing that we focused on was driving comp to drive behavior. So what are the key things that we're trying to achieve and let's build a comp plan that really aligns to those things. So we ripped up the initial comp plan pretty quickly and build a new comp plan. But again, all this stuff was much easier knowing that I had a rock that could really go run the business wide focused here.
Todd Busler (35:31):
Did you know those were the three key things when you were taking that role? Like, okay, here's the exact things I need to fix, or how did it become clear that, okay, hold on, I need to nail this forecasting thing. I need to get this rep profile set up?
Ryan Heinig (35:44):
Yeah, the action was fixed forecast. That's super broad. You got to spend time. I didn't make any changes for two months. I just live in the business. And then you start seeing things. You see things like, hey, three sales stages, that looks a little different. I've never seen that before. Okay, let's map out the buyer's journey. Okay, there's these different stages that they go through that doesn't align to our sale stages. What are the specific things that we do in our sales cycle? And then we'll make sure those specific things are aligned to the sale stages. So you have to take some time to really understand the business and then meet with the other stakeholders like get out of just sales. I spent a lot of time meeting with the delivery team. I flew over to Kuala Lumpur, Malaysia and met with them to really understand the business, really immerse yourself in the business is the best thing you can do before you make changes.
Todd Busler (36:27):
You said something subtle there that I want to dig into. On the forecasting part, you said, hey, we really needed to map this to the buyer journey. What do you mean by that and what are some mistakes you see when it comes to sales stages, which ultimately is built to help the forecasting motion?
Ryan Heinig (36:40):
Yeah, I'm a big believer that your sales stages should map to the journey that your buyer goes through when they're evaluating your solution. Is there a proof stage? If there is, we should have a sales stage that says POC. Is there a stage in which we go through and go through discovery and understand different use cases that could be applicable? We should have a discovery sales stage. So one, there's that piece really understanding your buyer journey and it's not obviously an e-com buyer journey like you and I are buying sneakers. There's a full journey that the buyer has to go through. They present a leadership, so there's that stage and all those things. And then from there, something that thoughts file is incredible at is really have this specific exit criteria. It has to be a non-negotiable. When I go from stage three to stage four, you really have to understand very clearly what stage you're in and why you move to the next stage.
Todd Busler (37:30):
What's an example of that binary outcome of yes, we can move from three to four.
Ryan Heinig (37:36):
So to move to negotiate, you have to actually send a quote, right? A quote is out the door, right? To move from MBN, the qualified opportunity, there's three things. You have to have a champion. It has to be an ICP fit and it has to be identified pain, right? If you don't have those three things, you can't move to stage four, which is qualified opportunity. Each one of those stages has a super binary thing that it can be checked yes or checked no, but
Todd Busler (38:02):
There's a lot here we could keep digging into. Ryan, we have about three more minutes. There's two last questions for you. What do you see changing in the next few years? I think the last two, three years, this game has changed a ton. Yeah, everything you're talking about around consistency, using your network, being creative, running the right operating cadence and rigor, that's never going away, but the tech and the AI and the volume that is changing quite a bit. What else do you see changing in the next six to 18 months when it comes to the PG motion? So first you
Ryan Heinig (38:33):
Mentioned in the beginning, I do think that the focus on services is going to change a little bit. Insight just made a pretty significant investment in us. Insight is historically a software investor and really their philosophy was that these next gen services companies, they have to exist because the amount of tech that people are buying, someone has to make this tech valuable and these next gen services companies like 2X have to be there to make these companies and help these companies not only execute on the tech they bought, but just help them in general help their operating model. So one, I think there will continue to be a shift from software to services. Software is not going anywhere. To be super clear, I still think it's the best place to work in all of enterprise sales, but I do think that services will continue to be more important.
(39:18):
To answer your question about PG, what do I think will change there? I think people are going to respond to less and less PG and you should use tools like Champify. You should really use your networks and one thing we haven't talked about, but I think it's critically important to invest in every interaction that you have. You could be on a discovery call and you know that this isn't the appropriate buyer, but I'm going to leave you better than we started. You take that call for the referral to go help them get a new job. One thing that my team does a lot is whenever someone gets laid offers or out of work, we're helping them go find a new job. You got to build that network. There's going to get into a certain point where cold PG just continues to be super difficult and you got to find ways to be creative to break in the door.
Todd Busler (40:04):
What are other examples of how you take someone who's younger in their career, they don't quite appreciate playing the long game there great example of actually I know people that are hiring, we talk to great marketing teams every day. Here's some good talent. I can match these. How do you teach them on what are those deposits? How do you teach them on what good looks like there?
Ryan Heinig (40:28):
I mean, last time we talked about this on your last podcast where we literally have those 75 things to do an opportunity and they're all deposits. That's what those things are. And you teach 'em that, hey, you make these deposits so you can cash 'em in. I don't know exactly. I think the answer would be like when they come to me, every rep comes to me and says, hey, I see you're connected to this person. Can you go send this? No. And I say yes, but eventually the younger rep's like, how do you know all these people? How do you always get these people to respond and you're like, hey, this is like 20 years of doing the right thing. So I think they kind of have to just see it to believe it would be, I think my answer to your question there.
Todd Busler (41:01):
Final question, Ryan, there's been so much gold here, I appreciate the time. Where do people trip up as they're thinking about career acceleration? Look at your journey is really impressive. Awesome companies. You've picked good runs there. You can see that not only you built your network and your quiver of skillsets and have people want to follow you to every opportunity. Where do people go wrong there?
Ryan Heinig (41:22):
Yeah, this is a super simple answer for me is vest in a or focus on the right company with the right training and the right mentorship. So when I left Qlik, I was a leader and I went back to being a rep. I was told by everyone that AppD had the best training program and it is by far and away the best thing I've ever done. Every single person that I've talked to ever since then says, oh, you're at AppD. You went through the training and it did. I really got my MBA and how to sell at AppD. So do not chase titles. Do not say, hey, if I'm not a second line leader in two years, I never was the person that said, hey, I wanted to move into this role. Every role I moved into, someone pulled me into that role. So I think the best thing you can do is find mentors that are great and learn and go to great companies that really invest in sales enablement. And you're starting to see this a lot. Organizations are really investing in sales enablement. Learn as much as you can. The rest will just happen because you'll be successful if you learn a lot and then people will pull you into new roles.
Todd Busler (42:22):
Ryan, this was awesome. Tons of gold. Like tactically on what does a sales stage look like? How do I fix this? Forecasting to big picture, picking the right companies to building your mentors to understanding, add those deposits to where the market's going. I appreciate you taking time. I appreciate your mentorship to me, and I just see you are a master of the craft and you probably still feel like I have so much to learn and I think that's what makes this thing we do every day. Interesting.
Ryan Heinig (42:51):
Yeah, always fun hanging out with you, Todd. Appreciate it.
Todd Busler (42:53):
Appreciate it, Ryan. See you. Thanks for listening to Cracking Outbound. If this was helpful, let us know by messaging me Todd Busler 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.