Subscribe
Share
Share
Embed
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.
Isaiah Crossman (00:00):
What everyone says on LinkedIn right now is the new way of doing app. And by the way, yet another thing I don't agree is I don't think sales has really changed at all in the last eight and a half years that I've been in this game. It just varies from vertical to vertical, deal size to deal size, segment to segment, whatever, but the game is still the same.
Todd Busler (00:20):
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 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.
(00:47):
Hey everyone, I'm really excited to have you listen to this episode with Isaiah Crossman. What's really interesting about Isaiah's background is he was a little bit later in his career to get into sales and he joined a company called Wunderkind on the road from zero to a hundred million, doing super big deals, true enterprise selling. After that, he partnered up with some of the early folks at that company as they started Tropic and he joined there as the first sales rep and left four or five years later as the CRO.
(01:17):
He has hot takes on things like discovery and qualification and first meetings. And what I took away from the conversation is someone that can balance sales leadership but also getting very deep into the weeds. You're going to enjoy this conversation. There's tactical tips, there's strong opinions, but you'll leave with some actionable advice on how can I be better in my role today. I hope you enjoy.
(01:42):
Isaiah. What's up man? I'm really pumped to chat with you.
Isaiah Crossman (01:46):
Likewise. Good to see you.
Todd Busler (01:47):
Yeah, been a while. I think we went to that dinner we put together maybe like six months ago.
Isaiah Crossman (01:52):
Yeah.
Todd Busler (01:53):
You're one of the few people I really like their content. I feel like you go against the grain in a lot of things and most of the things you say I am like, that's right. Yeah, we've been trained on this other stuff, but I feel like the way you've approached it is this is what really works. I've done it and I really appreciate that about your content, so I'm excited to dive into it and hear some of those takes. You had a crazy run. I think you went to AE to CRO in four years. I'd love to hear about that journey and from your perspective, what were the main reasons you were able to do that? Because it's pretty rare.
Isaiah Crossman (02:29):
And before I even answer that, just on the content stuff, one, I appreciate it and that's kind of what I'm going for and maybe to just get into things that people might want to know or hear. There's so much advice about how to create content and I thought I would never post on LinkedIn. I honestly still can't believe I'm doing it, but when I started I was like, you know what? I love to teach sales and I feel like I have something to say and I'm not going to play the games, all the little tactics and strategies. I'm just going to try and put out content that I would want to read that I think somebody would send in a Slack channel to someone else that they know or someone that they work with, someone who works for them, and over time it would work.
(03:06):
And I really think at least for me it works. I don't get as much engagement as huge profiles and all that, but if you're going to do that stuff, just post the most valuable things you can. That will for sure over time went out. So I appreciate that. And yeah, I think that's how we met in the first place was just trading comments and stuff on LinkedIn and I've met so many interesting people that way. Yeah, so the run at Tropic, I got into sales like eight and a half years ago. I did two years of consulting political campaigns before that and I knew I wanted to get into sales. I didn't know anyone in sales, I know anything about sales, no, in my family was in sales and I just thought I could make more money and I thought I'd be good at it.
(03:38):
And so I learned to sell at Wunderkind, which is a MarTech company in New York City, world-class sales organization, especially when it was run by the former CRO, like the person who taught me everything. So the two Tropic founders worked there, they hit me up. They were like, Hey, we basically need to hire founding ae. I was just starting to think it was time to change roles. It's the only role I looked at and a couple things stood out to me. I was like, for sure I could sell this product. That hit me immediately at the moment I started looking at it. So if you want to go on a wild run, if the product isn't good and you can't sell it, no matter how talented you are, nothing matters. And then I would just say I'm not at all trying to be arrogant or anything like that.
(04:19):
I think in these kind of situations when you're going to teach people about sales or whatever, it's you have to establish a little credibility. And I think I am a very good fundamental sales rep and I think that was my secret. When I was at Tropic, I got there closed $1.1 million in five months myself that doubled the ARR of the company and then the CEO is basically like, do you want to take over the team? And then from there on out, as the team performed every quarter, we kept hitting numbers. The machine worked. There would be quarters where we'd be way behind, come from behind, hit the number, and so when you become reliable, you just move up and I mean right place, right time. And working for founders who I believed they had a mindset where they were like, if you do this for us, we will help you and make it worth your while.
(05:02):
And they did. There's no real secret trick. It's just like do the job, execute, play your strengths. And maybe I knew there was an asymmetric bet there that I was going to get good odds on. Maybe the average a person who'd been selling for six months might've had a one in 20 chance of becoming CRO Tropic, but I'd been selling for five years. Most people who'd been selling for five years at an elite level on a strategic team wouldn't have taken that role. And so I saw that bet and was like, I think this is going to work and work for me. And ultimately it did.
Todd Busler (05:32):
I think that's super well articulated. Most people that could do that job really well, it would be deemed as too risky. You're usually getting someone a little bit too junior. My story at Heap was very similar. They're like, I think you could do maybe 400 to 700k in the first year, and I did 1.4 or something. And then all of a sudden they're like, okay, teach other people how to do this. There's usually a handful of critical or pivotal moments that they're pushing the chips in again on you because the board's telling them, Hey, go get the more senior person that's been there, done that. Do you remember exactly what those critical moments were?
Isaiah Crossman (06:12):
Well, I think, to be honest with you, the CEO Dave just had my back very extensively through that period for a long time where I'm sure there were moments where the board was saying that, but the team was performing so consistently, at least for the first few years before Tropic had to pivot a lot. A lot of companies in that space had to change their businesses, but during the main key runup, I think Dave had my back really extensively. And so I don't think especially in those first few years, there was really much risk of that happening. If we hadn't been performing, I think the story would've been different, but I think it was just, yeah, consistency. The sales team always had really high engagement scores. You think a sales team, everyone's unhappy, the management sucks, they're brutalizing the team. And I think we were just very nice to the team.
(06:58):
It was fun to be a part of that team. People enjoyed working there, so it was like, what were you going to change Again, not to be like, I'm not trying to be self-aggrandizing or anything, but it was like the people on the team liked working there. I liked running it. The founders liked having me running it. For the most part, it was good. Maybe some executives from other departments didn't like me. I was very insular. No one allowed in our Slack channels just kind of marching to the beat of our own drum. But yeah, it worked at least for a while. I don't think there was any of that really.
Todd Busler (07:24):
That makes sense. What role, Isaiah, did outbound motion play in that journey? Did you have to figure that out early? Was there like, hey, you came in and there was a ton of inbound. Just walk me through how it went.
Isaiah Crossman (07:34):
It's funny, actually, interesting question. So for that whole time that I ran that team outbound was like 80, 85% of our pipeline mostly generated by the SDR team. And is you said in the beginning, a lot of the things that I say on LinkedIn are sort of contrarian, but you're like, I agree with a lot of them. I think this whole idea that outbound is dead and SDRs don't work and you have to full cycle AEs only, I think most of that is not true, at least in what I'm seeing. I work across seven or eight companies at a time, and a lot of them are having a lot of success with outbound. So the way that I ran the team at Tropic was basically, okay, what is the target for next quarter? How much ARR do we need to book? What's our win rate?
(08:16):
What's our ACV? Okay, how many opportunities do we need if you apply the win rate in ACV to get to those bookings? And then how many meetings can an SDR book in a month? How many do we need to have? Is that economically efficient? Will our CFO or VP of Finance let us hire that many people and do that much prospecting and whatever spiffs we need to do? So that's kind of the first part, right? It's just the math, it's, it's all a basic formula, nothing complicated. And then where I maybe differ from some people on building an SDR team is I think a lot of people go and they're just like, we need these grinders, these brutes who are just going to rip a gazillion calls. And they're all former athletes and nothing against former, some of them are amazing, but the profile of people that I look for in SDR team is just really raw, talented people, great salespeople, a lot of career changers, former teachers, former product people who did other interesting things for a year, two years, five years, 10 years, 15 years, those people crush and then great sales training.
(09:14):
So at Tropic, this was the case for some of my clients. Now this is the case where their SDR teams, the cold call mocks the practice, really world-class training, treating that like a serious sales org, not disrespecting it. I think a lot of SDR teams get put in a corner, nobody cares about them. Also, I think you had, did you have Molly McElgunn on your podcast?
Todd Busler (09:33):
Yeah.
Isaiah Crossman (09:34):
Yeah. I mean our SDR team was run by an incredible woman named Molly. Molly McElgunn, who I hired. I ran the team myself for maybe eight months and then hired Molly. She ran the team the entire time I was there, got promoted multiple times. Absolute animal. Everybody loved working for her. And yeah, that was the story there.
Todd Busler (09:50):
What did someone at your previous role teach you? Hey, take enablement, take training, really serious. I think that's a common trap that the first leader falls into. So how did you know to do that or who was coaching you or was that an eight?
Isaiah Crossman (10:05):
100%. So when I was at Wunderkind, the MarTech company in New York City for almost five years, right up through the first year of COVID, that team was run by a guy named Adam Soros who is amazing, just unbelievable. He was the head of sales there, maybe he was even an AE originally. He'd been there for a couple of years before I got there. Ultimately became CRO. And he treated the sales team there like a sports team. And I mean that only in the sense of a lot of game tape, a lot of practice. We had twice a week, eight 30 in person in the office, in the morning training where we would do call reviews, training sessions, we would do all these mocks and competitions and it's like if your team didn't get a certain grade, you had to all do it over again.
(10:43):
And in the moment it was kind of annoying honestly, and we would sort of roll our eyes, but it fucking worked. And so I had just seen that playbook run. I didn't invent it, nothing. I was just like, when I looked back I was like, wow, I'm pretty good at selling now. I came in with zero sales experience and I wasn't very good when I started. And so I went through the journey of getting good with really good coaching. And so then I just replicated that. I knew when I took over the team at Tropic, I was like, what are my strengths and what are my weaknesses? This sort of classic, you'll hear the dashboards VP, I'm not that I don't do any process. If you want to improve forecasting, do not call me. If you want to figure out how to build out your Salesforce stages, do not contact me.
(11:24):
I'm good at figuring out what to say on the phone and teaching that to people. And so I knew that I was good at that already. And so I just turned around and started doing it with my team at Tropic and it worked good for morale, good for performance, attracts good people, and it creates this kind of Amazon flywheel-esque thing inside of a sales org. So yeah, I'd seen it done and I just did it myself. And yeah, that's how I ended up doing the consulting thing. I was like, alright, I just like doing this. And I started getting referrals from Tropic's board members, Wunderkind's board members, and I was waking up every day excited to do that work and I thought I was going to build a SaaS company when I left Tropic and then just organically ended up doing this because I liked the work. And so yeah, I saw it done and that's why I did Tropic.
Todd Busler (12:05):
I talked to so many sales leaders and it's the common theme is always we take enablement and training extremely serious. And I had a similar story, Isaiah, we brought in a COO and I was at he probably around 20 million and he's like, Todd, every Friday 9:00 AM you're going to lead sales training. I was like, every Friday is there enough topics? And there is, there's always stuff.
Isaiah Crossman (12:28):
And you can repeat them like every quarter.
Todd Busler (12:30):
You need to repeat them.
Isaiah Crossman (12:31):
Of course.
Todd Busler (12:31):
You need to repeat them.
Isaiah Crossman (12:32):
Yeah. Yeah, I did every Monday the entire time I ran the team at Tropic every single Monday, forever sales training, like 100%. And often we did sales training on Monday and call review on Tuesday afternoon. So it was a really serious cadence. I would do asynchronous call reviews. I would be like watching calls with a loom running, talking over them, saying them to the team. This is another place where I do think a lot of people get it wrong is like I was the CRO, Tropic managers, managing managers, big teams, and I would be in a Slack channel with the SDRs where they would post cold calls that they had done where they wanted feedback and I would send a three-minute voice memo being like, this is what I would change and that it just works. Everyone would listen. They would come with questions, there would be dialogue in the chat.
(13:13):
You need to hire a team full of people who are going to do that. But I'm sitting there being like, okay, so I'm going to spend three minutes listening to this call on 1.75 x speed and I'm going to record a two or three minute voice memo. The whole thing's going to take me six or seven minutes, but I'm going to get a 0.5% improvement in skill level just from this across my entire team. Exactly. And that compounds and compounds and compounds and compounds. And so it's like, yeah, a lot of sales leaders I think they go wrong is they sort of sit on top of a leadership mountain and they direct their enablement person to do this and that person to do that. And as a result, quality degrades at each stage of abstraction. And yeah, I think it's just like you have to be able to sell and then teach that to people in that just again, virtuous cycle.
Todd Busler (13:54):
A hundred percent. Talk to me a little bit about the difference in motion when it came to outbound at Wunderkind and then what you were doing at Tropic. From my understanding, where you were beforehand, super enterprisey, bigger deal selling to really sexy B2C brands. Tropic was super different. So what carried over to Tropic and what didn't and how did you figure out that motion?
Isaiah Crossman (14:17):
Right. So they were very different. And it's funny, what everyone says on LinkedIn right now is the new way of doing app. And by the way, yet another thing I don't agree is I don't think sales has really changed at all in the last eight and a half years that I've been in this game. It just varies from vertical to vertical deal size to deal size, segment to segment, whatever, but the game is still the same. What we were doing at Wunderkind back then is what everybody is promoting now. We would create a custom deck for Dick's Sporting Goods based on what we read in their earnings report and all this stuff, and we would FedEx it overnight to the CMO. And did they reply necessarily? No, but they were definitely seeing that being these guys are nuts. And so I was paired one-on-one with a BDR.
(14:54):
We had less than a hundred accounts, and so we thought about prospecting basically as, can we get a meeting with this company this year? It wasn't like we need to meet with them tomorrow or even this month. It's just how can we build a relationship with them, even not connected to them directly where it's like, how can we get a meeting sometime in whatever it was 2019 at Tropic? On the other hand, it was higher volume, more traditional, just like BDR, send a lot of emails, make a lot of calls, but again, that worked for us. And another thing that people get wrong is they say, oh, you can't just send a lot of emails to people. Well, Tropic's product was new to the market, so when we were emailing people with just good email copy, you could break through because they'd never heard of it before.
(15:35):
And so it was interesting. If you sell Salesforce, a generic email is not going to accomplish much because everybody already knows about it. When they need it, they're going to let you know and they're going to buy it. But when you're like, Hey, have you ever thought about the fact that you're probably overpaying for software tools maybe a fifth of the time, and if you just negotiated them better and had great benchmarks, you could save 300 KA year. You don't need to customize that to them other than getting the dollar savings roughly calibrated to their company size to book meetings with people because if the subject line is good, they're going to open it. If the first line is good, they're going to read it. And if the message is interesting, they're going to respond some percentage of the time. And so just different motions, both can still work. It just depends on what you're selling and to whom and where. And yes, the batch and blast emails are getting less effective because there's just so much more volume. But I mean, this was working just a couple of years ago, and I do believe for novel products that solve problems that people have, you don't need so much personalization even today.
Todd Busler (16:32):
Yeah, it's really interesting take. I think people try to blanket every piece of sales advice, and I think what's unique about you is yes, you had two great runs, but now you're seeing 6, 8, 10, 12 companies and you're like, look, it matters. How good is this offer? How new is this?
Isaiah Crossman (16:47):
I have a client right now who books all of his meetings via, what's it called? On sales in the mail. I'm not kidding. Hundred percent. He's a founder, founder led sales. All of his meetings come from in mail and you might say, there's no way that's true. Well, guess what? He sells to somebody that most of the people listening to this don't sell to a different persona in a different industry. Those people, for whatever reason, he didn't know going in, they respond to InMails. I have another client, absolute animal, CEO, we've now hired two people for her team, a head of kind of like pipe gen and a really elite founding ae, the head of pipe gen, all of the pipeline comes from conferences, all of it, every single opportunity. And yet, yeah, that's not going to scale forever necessarily, but their tams not that big. The deals are humongous and that works for them. So it's like the generic pipe gen advice. You got to be super careful, try a ton of things. You're going to be surprised some things are going to work for you, other things are not. It's going to change over time. So yeah, it's just different across industries, all that stuff.
Todd Busler (17:39):
Yeah, it's gotten to the fact that I think you need to be way more creative to find that channel, right? Totally. Who knew that person thought it was InMail, right? They probably an idea was events, events. How do you go get that right consistently?
Isaiah Crossman (17:52):
This applies at the BDR R level too or the AE level because where a lot of BDRs go wrong, it's like when I look at a BDR team, let's say you have 10 BDRs and there's some people at the top of the team who are absolutely crushing it and some people at the bottom who are just accomplishing nothing. The people at the top of the team may have a couple of things in common. Of course they're working super hard, they're very persuasive, like really elite communicators, but they're also willing to just try different things and do different types of outreach. And the people at the bottom, they're almost always just ripping the same generic emails. Their cold calls never improve. They're not trying anything. And so it applies at the leadership level. You got to get your team trying different stuff, but also as an individual, you have to be willing to try different things across every top performing BDRI ever see, they're constantly iterating, constantly testing. They're listening to other people's calls, what's working for you? All that kind of stuff.
Todd Busler (18:38):
I want to get into some of the things that didn't work because I think there's probably tons of learnings you have there before I do, just in talking to you for 10 minutes, I'm in the Slack channel grading SDRs calls. Most CROs wouldn't be doing that. I'm sitting there every Monday leading the training myself. How does the personal discipline, either the mental reps, the habits, the willpowers, show up a for yourself and then probably subconsciously you've learned to look for those same skills and traits and people that you hire?
Isaiah Crossman (19:10):
Yeah, that is a super interesting question. I don't know a single top performer who doesn't have strong willpower, strong execution. I was just saying this to someone the other day, the best people just check a ton of shit off their lists all the time. There's outwork in terms of hours and then amount of work done per hour.
Todd Busler (19:31):
Hundred percent.
Isaiah Crossman (19:31):
And yeah, for me, I'm the classic example of in school, some classes I did great. In other classes I did horribly and it was when I was interested and when I was in consulting, I knew I wanted to get into sales. I remember when I was reading the sales playbook at Wunderkind, which was BounceX back then before I joined, I was sitting outside of my parents' house. I had five days in between consulting and starting at Wunderkind, and they sent me the playbook. It was a PowerPoint presentation. I don't even know if Google Slides was just a thing. It was a hundred page PDF. I think I was reading it, just having my mind blown where I was like, I love this. I had never thought about the fact that you could persuade people really, that somebody could give you an objection and you could figure out how to address it and handle it and whatever.
(20:17):
And I was just so intellectually stimulated by it that the reason I'm telling that story is because you have to like it. If you enjoy what you're doing or you have real motivation, maybe you don't absolutely love it, but you really need the money. Or maybe you don't really love selling, but you really want to lead salespeople for whatever reason. If you have some real motivation, you can be successful. The people who don't have that discipline, that willpower, I know one dude absolute star. I think he does selling, but he also has three kids. Never thought he was going to make as much as he does as an individual contributor. He's a little bit older, not super, but a little bit older. And so it came to that money later in his career. And whether you selling or not, you have three kids, you're the sole provider for your family and you're making a ton of money, you're going to go to the mats every day. And so I'm just running through my list. I actually literally keep a list of top performers that I know, but I'm mentally running through it. And there are zero people on that list who don't know how to put the work in when it matters. And by the way, those people also take care of themselves outside of work. There is some amount of balance, but those people know how to get work done.
Todd Busler (21:19):
There's not one great sales leader I know that doesn't have that Google sheet of hit list of the best reps. Everyone has it. I have it. Everyone has that. I think the one thing you said is super subtle. Look, the motivation thing for sure, you have to be into this thing and there's different flavors. You're right. The reason why I really liked Heap, I remember I was getting ready to take that job. I worked at Square before Heap and Square, if you remember, it's like 2014, like Jack Dorsey's the king. It was like that company was Rocket and I got an offer, you'll work at Heap. And I was like, I asked one of my friends who is early at box, very smart girl, really trust her opinion. And I said, I don't know how excited I am about the go sell product analytics. It's like charts.
(22:03):
Is that the thing that's going to get me going? And she said, well, look, there's two things you're going to be really excited about up and to the right. And then she's like, you're also going to nerd out on these business and figure out, okay, how is this piece of analytics going to help us specific part in their business? And you're going to nerd out and understand deeply about other business. And that was the thing I loved exactly. I was like, cool, there's five different ways that we can sell positive business outcomes to this company. I got to find the one and get them to just think I'm smart and helping them figure this business out. And by nature they're going to buy our product.
Isaiah Crossman (22:34):
I actually never liked procurement. I still don't care about procurement at all. It's boring and I really am. I think procurement is kind of evil, to be honest. Not the industry, but I think procurement, this is yet another contrarian thing where people on LinkedIn are always like, oh, you got to procurement. You need to involve them early and do all this stuff. And I'm like, I would definitely not do that. I would try and circumvent them as much as possible. Get the most senior person you can to body them out of the way because they are bringing a gun to what could otherwise just be a casual knife fight. And there's no reason to let that person jack up your deal if you don't have to. I guess I didn't love procurement in the beginning, but I knew I was getting ready to leave Wunderkind. I didn't look at any other companies, but I did know I wanted to go somewhere super small and build. I've always been very just entrepreneurial minded. So when I got to Tropic, it was like the building, the team that fired me up. That was what motivated me every day, not because I was like, wow, I want to solve procurement.
Todd Busler (23:31):
Right. There's also one other subtle thing you said that I want to double click into that I think has gotten infinitely harder in the last six, eight years with social media and how our brains are trained. There is something to be just said for who is the person that can turn off their notifications and get a ton of real work done in an hour? That thing matters a ton. And it's amazing how many people just bounce around. I'm like, you're not doing shit. You're not doing the actual work.
Isaiah Crossman (23:59):
When I was at Wunderkind, I was performing well, one thing that's great about being an AEs, if you're performing, you can do anything you want. And so this was pre COVID. Nobody worked from home. We were all in person in New York City, amazing office. And I worked out this thing with my CRO where I worked. I know that I'm at my best in the morning and I basically get dumber throughout the day. I get less control over my, I can't focus as well. It's more tempting to get distracted, whatever. So I would wake up in the morning, I would work for two or three hours at home. I would get every task done that I need to, no calls or anything, just like every email, prepare for every meeting, every deck, all that stuff work out at maybe eight or nine. And I would get up very early, go back upstairs in my building shower, then commute to the office at 10 or 10 30, get there 11, 11 30, take all my calls by three or four o'clock and I'd basically be done. But I was doing that because I was like, okay, I know I need to get all this work done in the morning. No one's contacting me in two or three hours. I can get everything I need to get done for the entire day. And my CRO was like, yeah, whatever works for you. Because again, it's just like, yeah, a lot of people won't take the time and focus to get shit done.
Todd Busler (25:00):
A hundred percent. Talk to me about, Isaiah, about maybe getting a little bit more tactically. What's one big outbound mistake you made earlier in your career or as you were getting at Tropic that you see a lot of reps fall into the same trap?
Isaiah Crossman (25:14):
So outbound mistakes, the only real outbound mistake I made, and by the way, that might sound like, oh, my outbound is so good. It's more just that I've been a part of a couple of really good organizations with other great people where I haven't had to reinvent the wheel. And so mostly if you just look at the top people on your team and do what they're doing, you can avoid a lot of key mistakes. But very early on when I was in ae, I was like, okay, I'm going to prospect myself, try and book some opportunities. And I just did what I thought sounded good. And what I came to realize, and actually only a year or two later once I started exploring LinkedIn more and all that stuff, is I realized what I was saying over email sounded exactly the same as what everybody else was doing.
(25:56):
And the reason that's a problem is because humans pattern match everything. So you look at your inbox and you're like, I can't read all the prospecting emails that I get. So if you see an email, you think it's a prospect email, you're probably just going to archive it right away, delete it, whatever. And you just, when you communicate in a salesy way, it just makes people match you into a pattern they don't really like. And so early on, I was doing that later, I was paired one-on-one with this incredible BDR, this guy named Jordan. He and I sat next to each other. We were one day apart in age, worked extremely well together, traveled a ton together, and we just worked the book really tactically, like I said, FedExing a deck overnight to A CMO. We'd be in Chicago for a couple of meetings and we'd drop off cookies at somebody's office again, let's just get a meeting.
(26:42):
This we wouldn't even be asking for a meeting. It's just like, oh, hey, it's your friends at Wunderkind, whatever. Yeah, just generic messaging was the mistake and I still see it all the time. Oh, actually one other mistake that I see a lot generic messaging, but also I don't know that I didn't do honestly that much personal prospecting. Wunderkind is a very enterprise strategic style sale where we had a strong BDR team who supported the a's always, and some people are going to roll their eyes at that, whatever. We got to a hundred million in ARR with a dozen. So I dunno. But a lot of BDR messaging that I see today or app messaging that I see today is just robotic, very jargon filled. You almost read it. You're like, I have no idea what this means. So the mistake is messaging is just unclear, and I see this all the time today, sales messaging, this is a big area that sales teams can just fix in their sale is like stop and be like, are we talking in a way that actually makes sense?
(27:37):
Is what we say persuasive? Is it simple or is it really complicated? I was coaching A BDR literally yesterday for a client and the person said they were referring to some HR problem and they were like, oh, so we can help with your HR initiatives. And I was like, that means nothing. It's like just swap that variable out with your team has, like you said, there's a lot of low engagement right now. You got key employees who are leaving. We will totally eliminate that. That's way better than your HR initiatives. And so the swapping out the jargon for just English, that is the secret weapon for a lot of outreach and a lot of sales messaging in general.
Todd Busler (28:14):
Well said. A lot of your advice goes against the grain. I've seen you push back on the advice disqualify quickly. What's the risk in doing that early? Why do you feel that way?
Isaiah Crossman (28:26):
I just think disqualify quickly. I think there's two reasons that it happens that this advice happens, which we need to address on LinkedIn. There's certain advice and certain kinds of posts that just hit every time. And if you post that, the reason it hits is because a certain class of AEs who are very lazy and seeing that advice makes them be like, yes, you're right. I should be disqualifying except I should only work the best, most inbound cruising like a missile to closed one. And so it's very validating for a certain kind of person. And so it gases up the post and then it feeds. People want to do more of those kind of posts and back and forth. But the reality is sales is about persuasion. If you think it's a good idea for the customer to buy your product. So if you do discovery and you learn their business context, like Champify, you could tell me if I get this right or wrong, but if I'm talking to somebody and they're not sure they want to move forward and it feels like maybe it's not like a great op and so I'm thinking I might disqualify them or an A, you might disqualify them, but I know they really need pipeline and I know that they've booked some meetings and closed some deals from people that used to be clients who moved jobs and that kind of thing.
(29:37):
I'm like, I think it's probably a very good idea for you to use this product. The ROI is going to be super clear, it's going to work. You're going to make money from this thing and you need the opportunities I'm going to push. And so if we take that first meeting and maybe you're not the exact right person, but the company's really qualified, I'm going to navigate the organization to get to the right person. Maybe you're not super excited yet. And so A would be like, well, they're not a real ready to buy. They have no budget. Okay, well maybe I can convince you that you can get budget if you don't have budget today, I'm going to try to teach you how to position this to your CFO so that they will approve budget because your CFO probably cares about hitting the plan this year. And if the plan is at risk, even if you're like a junior enablement person and you don't know what the plan is, I think there's a decent chance that I can convince you that it's at risk or help you realize that it's at risk and then help you make the argument to your CFO that, dude, we should probably explore this seriously, even though we don't have a budget, it's going to pay for itself.
Todd Busler (30:34):
Very similar to how we think. We always talk about. It's the same thing. Once you have that conviction versus not, you treat them very differently. And if you don't have the conviction, we can really help them. You're absolutely right. Do not spend time with these people. But these people may not realize, and you're the expert, you've been talking to all of their peers, you job in the first meeting is to light them up. The job is to get excited.
Isaiah Crossman (30:57):
It might take four meetings, but if it's a good, those four meetings are probably a better use of your time than trying to get some perfect net new opportunity. And by the way, most AEs are going to have a very hard time convincing you that they're so busy that they can't take those meetings. Look, if you work at OpenAI and you're drowning in opportunities, by all means be very picky, but most people are not. And so I really think that advice is pretty dangerous, honestly and kind of insane, but I don't think that many serious people are actually doing that. I think it's just this thing that makes the rounds on LinkedIn for the reason that I said that it plays amongst people who want to be let off the hook for not wanting to push their customers.
Todd Busler (31:36):
You said that people tend to overcomplicate discovery. So going even a step further or in those four calls that you mentioned, what do you mean by that? Where do you see people go wrong? And again, I think your vantage point is super interesting right now based on what you're doing day to day.
Isaiah Crossman (31:50):
So discovery, people just get these super complicated methodologies and 19 letters and an acronym you can't remember and lists of 47 questions you need to ask. And they sound salesy and oh, just so much stuff going on. Discovery to me, the way I teach it to people, and I teach a lot of people how to do discovery and this is all of it, this is what I would teach to a sales team that was paying me a lot of money is basically it's your job to figure out if it is genuinely a good idea for the customer to buy your product. We talked about this a little bit. That's it. If it's genuinely a good idea for the customer to buy your product, you're going to just use that information to make the argument for why they should then buy the product. So again, we'll just use Champify for example, but you could tell me if you want to use a different company and we could try to do that as well.
(32:38):
If I'm a product that I was going to help people generate pipeline and bookings from the best potential customers, people who've worked with them before, I'm going to try and figure out do they need pipeline? Have they ever gotten opportunities from these people? Do they have people who move companies? Are they the kind of company that invest in things that have high ROI? And if those things are true, then I'm going to try and use that to be like, all right, look, Todd, here's what I heard from you. It sounds like you guys are in this situation where you're doing pretty well, but the targets are getting bigger and bigger every quarter. And so you have to find new ways to get pipeline. And it sounds like emails aren't working as well, calls aren't working as well, and you've seen some really warm meetings turn into opportunities and deals really quickly and we would go from there.
(33:24):
So that's part one is just like, does this person need the product? And then there's only two categories really of information you need in discovery. What are the goals that the company has and that ideally are goals that matter to executives, and then what are the challenges that are blocking those goals, challenges we can solve. So again, Champify goal hit your number more bookings. Maybe they want more warm opportunities, challenges blocking those goals, email's not working as well, phone not working as well, trying to get those opportunities manually through sales nav. Everybody on link is like, oh, sales nav can do that. Can't. It's so hard to do that through sales navigator. And so it's like, okay, if we have goals that you need and there's challenges we can solve that are blocking them, then it's probably a good idea for you to buy the product. And that's really it. I don't think there's much more to it. I don't think you need complicated. I don't think you need ban, whatever. If they don't have budget right now, again, you can convince them to unlock budget. Almost any company on Earth will spend money if you get to a senior enough person and you're doing something they care about that they can't easily do on their own.
Todd Busler (34:25):
We think very similarly, Isaiah, we talk about that all the same time. Pretend you're in their shoes, get on the same side of the table. If you think that's a really good idea for them, then act like it. And that's the exact thing I think where people go wrong is then, yeah, it might be a good idea for someone Junior. You have to tie it to those goals. You have to tie it to an exec goal. I think that's where people struggle.
Isaiah Crossman (34:47):
People ask these really esoteric open-ended questions of what would it mean for your business if like this or what are the negative implications of if you didn't do that me, I would be like, yeah. So this might be an obvious question, but I guess are you guys in a position right now where you're like, we really do need more pipeline. Are you starting to think about just new ways you can generate pipeline? And I'm fine if the answer is like, yeah, for sure. That's way more helpful to structuring the sale to me than some weird question that may or may not ultimately circuitously wind. It's... no buyer wants to sit through that. So I think you can get real simple with how you talk to customers.
Todd Busler (35:29):
A way I've tried to teach around this, and we spend a lot of time on this, is yeah, you can give any rep with a pulse a list of discovery questions, but a lot of times they actually don't know what the answer is they're looking for. Totally, right. So here's examples of what you're wanting to hear. Here's a generic thing that's probably not going to help us. And I almost find that the example answers are more important than the questions.
Isaiah Crossman (35:51):
I was just helping a client with their, I guess you call discovery scorecard or call one outline the other day and the first this company called Letter Drop. Sometimes I post about them on LinkedIn, they help people book pipeline through LinkedIn. And the first question on the scorecard is just does this company need a pipeline and need is in all caps and there's a million reasons that somebody could need pipeline and a million ways you could answer that. But that's what we're trying to find out is do they need pipeline? And it's basically do not pass go until you've confirmed that or not. And then next question is have we agreed with this customer that they believe LinkedIn is a real potential source of pipeline? If you need pipeline, but you do not believe at all that LinkedIn can generate pipeline, you're probably not going to buy their product and it's probably not a genuinely good idea for them to buy it. And so it's very simple general questions you can ask anything you want to try and then uncover that. I guess that really is what I mean about overcomplicating discovery versus just like, let's just answer that, genuinely answer that question, let's have a normal conversation with them. We'll see where it goes. Every discovery call from good a's sounds different because answering those high level questions not running through their script.
Todd Busler (36:56):
Exactly right. Yeah, they should sound very different because you're going with the answers and it's hard for reps to figure that out. Okay, last point. I want to dive into Isaiah. I think I could talk to you for five hours about this stuff. And I think that getting this tactical is why you've had the success that you've had. Talk to me about what it was like competing head to head to event with vendor. And the reason why I asked that is I feel now categories are more competitive, there's more people fighting for the same dollars. You have to figure out how to a rip out budget or have good competitive win rates, ideally both. So talk to me about what that was and from my outside perspective of no one that spent, I've never spent time in procurement. It seemed like vendor was kind of first to some of this, the brand might've been a little bigger. So I'm curious how you guys approach that. And again, that's my perspective.
Isaiah Crossman (37:44):
And just again, I'm not trying to guess myself or the Tropic team up, but just to establish some credibility on this point. When we started, they were way bigger than us. I think they were eight times bigger than us, employee headcount, all that stuff. And over time then it was four times bigger than us and then it was like three times, two times and one and a half times, and then we became the same size, then we were a little bigger. And so I think we did. And by the way, they were a very fierce competitor to be clear, a lot of very smart people there. They did a really good job. But we also, we played it really hard the way that we approached selling against a competitor. And this by the way actually is kind of the one way that I think sales has changed a lot is it is just more competitive.
(38:25):
Every product has more competitors. And so this particular topic is one that I think everybody should invest real time in. So winning against one, you have to have something to differentiate on. And a lot of products are very similar, but you must find the thing. Ideally it's like one or two key things and then you have to convince the customer that thing matters to their evaluation. Once you do that, you need to then teach them how to successfully use that internally and you need to validate that it's true for them. And I'll give a couple examples of this in a second. And then the only other thing that I think really, really matters in competitive sales is how you sell is super important. If you build a great relationship with the customer, if you're super on the ball, if you reply faster, if you're nice, if you're easy to interface with, again, if you really help them sell internally, we got this feedback a lot honestly selling against vendor where people would be like, look, I'm going to be straight with you. You guys products seem exactly the same. I have no idea which product is better, but you guys are just way easier to work with. And I'm sure sometimes vendor heard the same thing to clear, but I think we heard that more often than not. And just sales execution goes a really long because people are like, they're making a judgment about what your company is going to be like to work with after the sale based on the information they have.
Todd Busler (39:41):
If Isaiah nails it, I'm going to assume the success person implementation.
Isaiah Crossman (39:44):
This is a company with smart, hardworking people. Then it's a company with smart, hardworking people, which by the way was true about us. So let's go back to differentiation though. So you need to pick your thing. So I'll give an example from Tropic versus vendor that's years old. So not talking out of school or anything, but for a long time we really did a good job just leveraging our service level as a differentiator. And this is another thing on LinkedIn, people are like, oh, you can't, service level shouldn't be a major factor and say, okay, well it was for us and it worked. And the reason was we just made it seem really important to the customer because we thought that it was, again, back to genuinely a good idea. Anything that you genuinely believe is good for the customer, you should feel totally free to push hard on.
(40:23):
And so here's the real trick is you need to start planting the seeds for that differentiation long before a competitor is ever mentioned. And the reason for that is because you want to make it part of your customer's evaluation. You want them to think it's important and to really believe it's important again, before they think you're trying to differentiate. Because once they're like, how do you compare to vendor? How do you compare to your main competitor? Everything you say after that is tinted by the fact that they think you're kind of being nasty. So what I would do is early in a discovery call as I'm talking to the customer, and this is another example of simplifying discovery too. I'd be like, one thing that I also want to ask you about Todd is how are you thinking about the kind of service level that you're going to get from a potential provider in this space?
(41:06):
You're thinking about outsourcing some of your procurement work and you need to set up this new system. Are you guys the kind of people where you're like, oh no, we set everything up, we're very autonomous, or do you feel like making sure that the partner you're going to pick is going to really hold your hand through it and set it up for you? Is that a major factor for you? I'm not fishing either way. I'm just curious what your take is. I am a little bit obviously fishing for the latter, but if it's the former, that's fine. And so I ask that and I'm planting that into the conversation and then you might say, yeah, for sure. Most people are like, yeah, we want help and support. I'd be like, okay, great. That's something that a lot of our customers I think about as well, and that's one of the main reasons people who do end up working with Tropic, it's one of the main things they think about.
(41:46):
And then 12 minutes later in the same call, repetition is so, so important. So now we're talking a little bit more about Tropic and I'll be like, by the way, this thing that we're talking about right now, we're going to set all of this up for you. That's again, where our service level becomes really important. And now we're on call two and they're like, Hey, by the way, we are also talking to vendor. How do you guys differ from them? And I'm going to be like, well, whatever. There's a couple things there, whatever. But one main thing that customers who end up going with us who look at all the options, one of the main things that they say is they really do point to the thing we've been talking a lot about, which is our service level. And really it's like now the stage has been set that's already important to them.
(42:23):
I'm just kind of like, yeah, it really is just that. That's the main thing. And then I help them validate it. So I'm like, I've got stats on how many CSMs do we have versus how many CSMs the vendor has. At one point we were like, okay, they say they have 500 customers on their website. How many CSMs do they have on LinkedIn Sales Nav? How many customers do we know that we have? How many CSMs do we have? We'd be like, our ratio is way better. And so we'd be like, validate the service level, have customers be willing to talk about our service level in reference calls, so make the differentiator important, then help them validate it. And then the CSM ratio stuff, we would send that over email in a side-by-side table, just really good helping them sell internally. All of that bang that drum over and over, tons of repetition. There were lots of other differentiators that we used over the years. It's always cat and mouse. They figured out we were saying service level. Then they started to improve their service level. Talk track. Now we need to talk about this, talk that whatever. I don't know if that's a helpful answer or not.
Todd Busler (43:16):
It's an amazing answer. I think I was just talking, I had Ryan Heinig, who I think is one of the best sales leaders out there. He was at Qlik then ThoughtSpot, AppD and now is this company called 2X. And he's like, look, I sold BI. If you had a differentiator in 60 days, you didn't. That's the reality. He's like, you can win on a better sales experience. And then same thing, I think you do a great job. People overcomplicate this like, oh, look at this table of a comparison. It's like, no, find the one thing and repeat it. And if they don't buy into that, you're in trouble. But get them to make that important.
Isaiah Crossman (43:48):
You asked me in the beginning of this meeting if I wanted to pump any of my services or anything, which I do not want to do, but I will take a very small moment to just pump one of my clients for this specific thing. I work with a company called Cram. They literally sell competitive intelligence software and all they do is that thing when it's like every 60 days, something is different, they just scan the entire internet all the time, all your Gong calls, every piece of information to be like, yo, these are the four things that are working right now to win deals against competitors. And then they make it easy for your salespeople.
Todd Busler (44:16):
Do them.
Isaiah Crossman (44:16):
Yeah. And it's like your salespeople can just slack the Cram robot and be like, Hey, what's the deal with obscure competitor A, B, C, boom. Here's the three things that the best people on the team are doing. That process, we used to do that so manually at Tropic, and it was actually this competitive thing that we done
Todd Busler (44:32):
On traffic that got me and the CEO originally connected. I don't want to put myself, but hopefully no one will mind pumping a company that I think is cool using the power for good. So I'm going to wrap. This was awesome. I could talk to you for hours. I think you have a really innate ability to simplify things and just be like, look, there's a ton of noise out there. Here is the things that matter, right? This is how you think about discovery, qualification, mostly bullshit. Light 'em up. Figure out how to win these competitive deals. Figure out your medium channel and be creative on the outbound side. There's tons of stuff here I jotted down even as I, things I know and I'm like, we're not doing that as well. And I could just tell because the way you describe some of those experiences, exactly what we feel right in so many different ways, which means there's a lot of people feeling this and I think this is one of the better tactical episodes I've heard. So I appreciate you taking some time.
Isaiah Crossman (45:22):
Dude. Thank you. This was awesome. I love the conversation and yeah, I really appreciate it.
Todd Busler (45:26):
Alright, take care. See you.
Isaiah Crossman (45:27):
See you.
Todd Busler (45:30):
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.