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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.
Andrew Berger [00:00:00]:
Sell, sell, sell. Because you not only get credibility with your team, you gain credibility with the executive leadership team. Like a felt learned experience is a whole different credibility level for your team. Like they respect you more and then for the company because they also respect you more.
Todd Busler [00:00:19]:
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 built it. Let's get into it. Hey everyone. I'm excited to have Andrew Berger join us today.
Todd Busler [00:00:49]:
He's currently the VP of Revenue at Capchase. We're of the hottest series B companies out there. Not only is Andrew a good friend, but he spent time at four different early stage startups leading sales in both the VP of Sales and CRO capacity. Today he'll share how the world of outbound has changed in the last decade and he'll go into details on exactly what he's doing. Building the outbound motion at a series B organization and rallying the organization around outbound and everything that goes into that. And enjoy. Berger. I'm very excited to be talking to you today. How are you?
Andrew Berger [00:01:24]:
I'm doing great. Todd, how are you doing, man?
Todd Busler [00:01:26]:
I'm doing great. It's been a while. I was thinking about this. We started at Square around the same time, more than 10 years ago now, which sounds crazy.
Andrew Berger [00:01:35]:
Yeah, I was thinking about that the other day that some of the people that we interacted with, it's like 10 years old, like from that time period. And just where that business was when we started slanging credit card readers, telling people on the phone directions to the app store of a physical credit car reader to a. Where that business is now, but also some of the fundamentals that taught us and then seeing like where our peers and our friends are in their careers. It's been a. It's been a fun decade.
Todd Busler [00:02:01]:
100%. Yeah. There was so much learning there that I don't think, at least I didn't appreciate that. Now I'm like, wow, okay, there was a ton in that business and you were there a lot longer than I was. That kind of shaped a lot of my thinking, I'm sure a lot of yours, which we're going to get into. But why don't you take a minute, Andrew, and explain Kind of how'd you even get started at Square? How'd you get that opportunity? What'd you do there? Like team size, revenue scale, just to set the tone for what, what we're kind of contrasting things to.
Andrew Berger [00:02:28]:
Yeah, it's a kind of fun trip down memory lane to think about it. So like over 10 years ago I found my way into tech. I'm not getting through a Craigslist job posting. I was a failed product manager at a company called Phanteks. And I say failed like my own failing, like I didn't know what I was doing. But it was a fun experience to sit next to designers, engineers and just absorb client server, just the terminology. As my first seat at the table in a technology job. I then met a few folks that we know together.
Andrew Berger [00:02:59]:
Ben Fisher, one of my buddies, his wife, now girlfriend at the time, Kate was I think was like in the first cohort of sellers hired with you and if we just drop name drop like Rosie and like Ross and Dorinus and all those folks that we worked with. And I was talking to Ben and Kate at the time saying, hey, like I think I want to get into sales. And Kate was like, hey, well, we're hiring a bunch of people at Square. So I interviewed and I remember Ross, and Rosie, and Darimus were in my interview cohort. Like my final presentation. I was like so nervous about it and luckily they passed me through and I did a little over like a year of selling Square. It was a great time. Like we all were hunkered in, like I think the sixth floor and then we moved up to the 18th floor or something like that.
Andrew Berger [00:03:39]:
It was just a exciting time when we're all relatively young in our career striving towards a mission like Square was hot. I think Aaron Zamos used to have this famous saying about the tech clock and the journey of a company. And like we were at that, that north star at that 12 o'clock and we were grinding hard. I was, I think I was given a phone book of Washington D.C. and said, Go call everybody to offering Square payments. Like a huge principle, right? Trying to cast a wide net and not understand like who your key Persona is or your ICP is. And so like you learn those things by trial and error. And over about a year and a half through that journey, we definitely hit some sort of plateau on the sales side.
Andrew Berger [00:04:14]:
And I think some of the principles that Square imprinted upon me was all new teams had to reach some sort of cliff of ROI and investment. So I remember Eric Sager distinctly would Be like hey, we give a dollar to marketing in X period of time they're going to give US$3 back. So the sales team has to be more valuable than those 3x ROI positive. And then every new initiative underneath the sales org how to be growing faster than you know, a growth rates and also like dollars and cents in terms of ROI positivity and value. So I can't remember all the details but basically we reached some sort of cliff in terms of you know back then it was panda processing volume and new merchants signed up and so like how do we grow? It was clear we were attracting very large merchants or large sellers to the, to the platform. However, not all of them were qualified and who would have thunk, let's do some qualification instead of routing all inbound leads to everybody. And it was just so much fun building from scratch. It wasn't easy at all.
Andrew Berger [00:05:11]:
A lot of cross functional work, a lot of, you know, sales teams. I'm going to take your leads away. Like who are you hiring? These like 24 year old kids like to, to take my leads. Like there was so much dynamics to overcome but we built a pretty good program overall.
Todd Busler [00:05:23]:
Looking back it's like all of that stuff is so critical today, right? And I think there's not many companies dealing with hey, I'm getting 5,000 inbound leads a month, what do I do with it? Right. But slowly, okay, how do I turn this outbound thing on? How do I make sure that it's high enough roi? How do I determine where to, how to scale that? Where do we scale that? What's the profile like? You had to learn so much there. What were some of the big kind of unlocks transitioning out of the more inbound ops, heavy motion to like all right, we're going to scale this outbound thing and how did you guys go about it?
Andrew Berger [00:05:56]:
This is kind of a fun trip down memory lane which is specific to square at the time. So there was through a lot of as you know, selling the, the payments product. We wanted to go find merchants that would do high volume of transactions through that journey. We realized not every dollar is created equal. So there was a level of ticket size, type of customer with interchange rates and credit card issuer fees, et cetera. So what we basically coalesced around was that QSRs, Quick Service Restaurants that had a ticket size of like 15 to $25, 15 to 50 bucks and doing a million to 10 million per year was kind of like our prime target square would reap the most amount of profitability on a per transaction size given the credit card mix. And also it was the highest like volume against existing cohorts. So AEs wanted that business, the SDRs wanted that business, the company wanted that business.
Andrew Berger [00:06:51]:
So how do we go do it? We did a ton of trial and error and through John Lee was really instrumental in some of this work which was talk about personalization, like now everything. The personalization, Personalization, personalization. I mean back then, I'm not kidding, we would look at a Facebook page of a restaurant, we would then go to the Yelp rating and we would find like the most highly pictured or rated food item. We would then take that and put that in emails or we would call people. Like we did a mixture of emailing and calling, like two channel approaches. And we just saw results skyrocket. It was pretty remarkable. And then the two branches like came through that.
Andrew Berger [00:07:33]:
I sat down one night in kind of the bullpen of Square and one of our sales engineers, a guy named Ben Hartard, came over and we're just kind of like chewing the breeze a little bit. And I'm showing him like what our process is to go check a. Does this restaurant or merchant already have an account inside of Square? Because again, we wanted to really bifurcate ourselves from the self serve business, from the sales led business because we wanted to prove we had to reach that cliff minimum 3x ROI positive on the work that we did. So we had a pretty clear line of demarcation. And so Ben's sitting with me and we're just kind of like shooting the breeze, talking about what is our process today. And we would sometimes try to find the contact person of who created the website of that merchant. We literally type in like in terminal, who is the website name, right? Who created the GoDaddy certification. We then go to the Facebook page, go to the about page, we then go to the Yelp page and I'm sitting with him.
Andrew Berger [00:08:29]:
We're talking about this. And I remember I got pitched on a tool called Datanyze, like in 2014, 2015, I'm talking to Ben, I'm like, dude, can we like do something like this? Like you're smart, can you figure that out? And I'm not kidding, like a day later he built this tool, Chrome plugin internal usage called Square Website Analyzer. You press the button on a website and it would branch off into like their Yelp page or Facebook page. Check against internal Salesforce internal tool. I think we use a platform called like Regulator or something like that. Doing all the automation, like Nowadays automation is everything. We did this 10 years ago and he built this internal tool. And so that is, I would say the principles of identifying a relatable object within personalization was one aspect.
Andrew Berger [00:09:10]:
The second piece was automating all the manual work that we're doing to be more efficient, to get more done over a fixed time period. And then what we did is we extended it even further. I worked with a company called Lead Genius. I was talking to them saying hey, getting local data is really challenging. You can get a bunch of different data but our target merchants that provided the highest value to Square were not indexed on LinkedIn. So it's how do we go find local information? Lead Genius model like had a mixture of software with contractors around the globe and they would go call and validate information and we were able to get in such a good rhythm with them that they would insert, they would do the manual work like on Yelp, the highest rooted food item and deliver that as a massive CSV file. Like one column was like best food item. We would then take that, import that into Salesforce, take that, run that through Sales Loft and then boom, we had automated through manual work our outbound prospecting, referencing their best food item.
Andrew Berger [00:10:10]:
And I can't even tell you like the response rates, the sentiment rates were like through the roof. And so in that vertical, in that motion, through personalization efficiency, working with third party providers, we're able to not only just like value added engine to the business, but pretty demonstrative results to the business for sure.
Todd Busler [00:10:28]:
And it worked because that part of your org under you scaled to you know, 7,500 people or something, you know, it's scaled to a real size and it's just, it's interesting you hear hear you talk about it because sure, the techniques might be a little bit different today or like you know, selling at Square is a lot different than Capchase or Front or Champify, but the ideas are the same. It's like how do I minimize non selling activities? Where do I get an advantage to understand who the exact accounts are and what can I do to get them to respond. In this example of sending them a picture of their favorite cheeseburger or ice cream. But like there was something there and it's this constant battle of like okay, find something that wins, go do more of it, scale it, etc. What else did you say were some of the big things you learned there? What I just heard was kind of a really big importance on operations and measurement, B really big importance on experimental kind of creativity and Always testing the envelope of how much more juice can we get from this? What, what else were some of the big things you took away because you, you learned under some great leaders there?
Andrew Berger [00:11:28]:
Yeah, I, I think there's like three critical elements that I've taken to my career under there. Number one from I would say Eric Sager. He's like the CEO of Plaid now. And Eric was all about efficiency and precision. What he taught me the most was like, how do we scale a program with automation and processes until we have to go hire the next person and every person we brought onto them especially. It's easy in sales, it's easy to quantify their output. Any person in the organization, whether it's pre sales or post sales, like there are metrics associated when we brought data to the conversation and we're able to explain the ROI from these activities and specifically I brought some initiatives to him that required headcount. He's like, no, go solve the problem first.
Andrew Berger [00:12:13]:
And until you prove that, then we can go, you know, hire folks if we even need to. That's more apropos obviously in today's market than when it was even five, six years ago. I would also say kind of a derivative off of that is Taylor Casino, one of my leaders. He made me think about like newer teams and organizations as he started a bunch of new teams at Square. Over his decade long career at Square, which was each sub team had to grow faster than the bigger organization. So if organization is growing at 200, you know, or 2x per year, this group needs to go 3x per year. This smaller group needs to go 4x per year. Right.
Andrew Berger [00:12:45]:
Or some variant of that. And we would sit down together and he'd be like, okay, I want you to treat me like I'm your angel investor. I'm going to give you dollars. I'm going to expect a return back. And Eric and the other senior sales leaders and business leaders are your investors. And so like we're going to have to, on a quarterly cadence, start to prove what we're doing, ask for buy in, enroll them and include them into some of the thought process and decision making. So those two aspects are like really helpful in my career. I'd say two other pieces was how to hire folks.
Andrew Berger [00:13:15]:
Blessing and a curse. At Square, you put an SDR job online, you get 500 applicants in like two weeks. 2014, 15. Like we were private, then we went public. Like Square was hot, super hot. Incredible pedigrees of people from every Ivy League school under the sun, international schools, MBAs and whatnot. On paper everybody looks really talented. But then how do you actually tap into like the human psychology and human aspect and through trial and error.
Andrew Berger [00:13:39]:
Everything's testing. We would test different interview practices and whether we give them a case study. Zoe and I would, we, we gave some folks like 50 leads and say ranked them top to bottom who you'd go after and why. Or you get 50 leads to go prospect into. You can only have time to go after 10. Why did you choose these 10? And walk us through how like we wanted to know how people think, not just like what have they accomplished that has led to like some folks we've worked with are, you know, basically VPs, directors, investors now starting their own business. It was, it was hired some amazing people. At this time I only worked with like one organization.
Andrew Berger [00:14:12]:
I worked with a company of 40 people. Then I got an escort, was 400 people. I left it was 4,000. I think it's now close to probably 12, 13,000, something like that. And the ripple effect of people you have to work with and how you have to get along with others and build relationships. I had to go create new job levels in the architecture. Like I've never talked to an HR team about new job levels. Right.
Andrew Berger [00:14:34]:
I had to go create new sales comp plans with sales finance. I never created a comp plan before. This is, you know, 10 years ago. And so all those learnings were net new for me. And being able to, I would say the key learning there how to work with a business partner and understand what drives them, what motivates them, what's on their okr. So that when you come and ask someone to do something for you, you understand where they're coming from and how you can both kind of work together. So I would say like those three big topics were absolutely like lifelong learning for me in my career.
Todd Busler [00:15:05]:
There's so much to unpack there. One thing you didn't say that I'd love to hear you talk about a little bit is kind of look building in this example SDR inside sales org from single digits when we started to hundreds. Right. Talk to me about how you drove accountability, drove the right behaviors in an organization, performance management and kind of what you learned over your journey there because that's applicable to anyone listening at any stage. And I think like you got insane number of at bats in a quick amount of time and I'm sure you've learned a lot from it.
Andrew Berger [00:15:40]:
Yeah, it was trial by fire and I was not good at it when I started. And I remember distinctly the first quarter of like having a real team like six to eight people doing inbound, you know, six to seven people doing outbound. This is a, this is a big group as like a first time leader comes from athlete background, sports background. You know, you and I both played sports growing up and I just wanted to be the best at what I did. And so I would work hard to do whatever I got to do because that's just who I am that's came through my family and whatnot. And a result of that was, I can't remember, I think it was the end of 2014 or something like that that we did some like sales awards and Beth back in the day gave me a energizer bunny because I didn't even know I made the most amount of calls over like a quarter or two quarters. It was like some like goof trick, right. And what that thinking to me was like I knew what my goal was.
Andrew Berger [00:16:28]:
I just wanted to be the best. So I'll do whatever it takes. I honestly didn't even count my calls or demos or emails. I just did what I believed internally was supposed to be the most. Now when you manage people that's very different. I treated that first team like I treat myself. Here's a quarterly target, here's what we're going to go do. You guys know what we're going to do.
Andrew Berger [00:16:49]:
I brought you into the mission. This is where we stand in the company. This is we're doing for the business like this. We're all connected together. Go. And when I say go. Yes, we did one on ones and stuff like that team needs. But I wasn't obsessing over monthly metrics, weekly metrics, daily KPIs.
Andrew Berger [00:17:03]:
At the end of the quarter we have pretty bad results. Like it wasn't good and I got like concerned and I had some reflection and talked to our leaders and it was my first like smack in the face learning about. You have to learn about how individuals are motivated and what matters to them, but also that they are not going to respond how you respond. And I'd say after that first quarter of like step on the rake, hit myself in the face type of learnings I took. Then the quarterly number broke it down to monthly, like it's not a novel concept. Broke it down to weekly and broke it down into daily KPIs and we ended on right, whether it's meetings booked and emails and calls and all the activity metrics, the leading indicators, lagging indicators and we had so much volume right. Like it was A pretty easy mathematical equation of what we can produce. So in terms of accountability holding folks to, yes, sometimes there's fluctuations per day, but we're going to strive to hold weak to daily KPIs.
Andrew Berger [00:17:56]:
And it was really what matters most is what we're doing over giving week. I would say, like, early in my career, I was really bad at setting expectations and I was really bad at having crucial conversations. I would say in Square's journey at that time period, going from 400 to 1,000, 2,000, 3,000, was a huge emphasis on people leadership and people management. And I was grateful that I was put through a lot of different programs of how to, you know, whether it's Kim Scott's radical candor or crucial conversations or the litany of books and processes, like, there are programs designed for emerging leaders, which is really nice. And I would say my time at Square, I was probably a really bad expectation management setter. I was probably really bad at having direct conversations. But those principles have applied and I've taken what I've failed at and what I learned to where I am now where setting expectations, having difficult conversations, getting the best out of people. I wouldn't say it's not easy, but it's more natural because of the volume of at bats that I had over that kind of four and a half, five year time period.
Todd Busler [00:18:56]:
I feel the same way. Right. Like I was, I left Square, I joined Heap. I never managed before. All of a sudden I had a team under me. You're trying to figure it out. And I would say wired very similarly in that, like, all right, I'm gonna outwork everyone. I'm gonna show them what like the level of effort looks like.
Todd Busler [00:19:11]:
But people are not wired the same. But what I want to do now is talk about what's your current role. Right. And kind of show the distinction between how that world has changed. Because I do think there's a lot of similarities. Sure, the buttons we're clicking or the strategies we're doing are different, but there is a lot of similarities. So what's your current role today? What does outbound look like on your team? And maybe just frame it up on, hey, here's what I kind of walked into. And here's, here's kind of the mandate as well.
Andrew Berger [00:19:37]:
Yeah, great. So my current role as the VP of revenue at Capchase. And Capchase is the number one financing platform for buyers and sellers. And so specifically what that means is that we finance contracts. Think of like enterprise contracts where, where we can then remit or give the Full payment of that contract over up to five years to the vendor. So think about public companies or emerging enterprise companies that have very strict payment terms, processes will underwrite to the vendor and then we collect monthly accordingly from the buyer side. And we do this in a very technologically driven way through CRM integrations. We have our own apps and we automate a bunch of work.
Andrew Berger [00:20:17]:
We do a lot of like LLM modeling on credit and risk behind the scenes and a lot of taking proprietary data and external data to look at risk profiles of buyers and even vendors. So I'd say like the corollary here is like back to payments esque, Back to fintech. What is fun about it is the journey that I took at front on quality on Pave, which it was very different than Square. I feel like Square was all about volume and payments and finance and the other three roles that I had was all about proper B2B solution selling. You and I both went through force management command the message, different tracks, I went through them twice. And so all about the change curve, right. And the value added conversation. And so many principles align.
Andrew Berger [00:20:57]:
And where I'm at at Capchase we're targeting and we go after we work with enterprise software vendors and we bring software to the equation. But now we're talking about back to payments as well. And so there's a mixer mixture of bips and software solution selling which is actually pretty fun. So it's been a pretty fun ride. I started in September of last year and what I walked into, I would say on where the business is focused in what we call the Capchase pay product infancy. I mean we're talking about started really going after commercial efforts the beginning of 20, 24, 400k, 500k like annualized ARR and we're just passing 5 million right now. And so it's kind of like one of the concepts that stacks over time, right? When you have payments and contracts stacking over time, month over month, quarter over quarter. I'd say I walked into a team that was trying a bunch of different things at once and we have a really cool growth engineering team which I've never worked with, but have a list of like 20 different tools that they use multiple different email domains from IO to AI, you know all the, to try the different email inboxes and all the campaigns.
Andrew Berger [00:22:04]:
We have very talented people that can go and look at who's following who on LinkedIn proprietary data and try to match some models that way. We do some competitor campaigns. We're doing a lot of different Things I would say we are now trying to figure out at this juncture, I would say the past six months we've learned, I forget revenue segments, but who has used financing and who has not used financing are two very different motions, different messages and different sales or go to market tactics. So that's like a key aspect on our side that we're now just kind of learning and even if you take it downstream, have radically different margin implications to our business because there's a market rate that folks demand and then there's kind of greenfield opportunities where we can make more margin when we're bringing folks into this category for the first time. So two very different motions.
Todd Busler [00:22:51]:
So that bifurcation, this is really interesting and I think this is actually becoming a lot more prevalent right now. It used to be like, hey, let's pick the account and we can see the industry or the employee size or sub vertical or hey, do they have the presence of this role or not? And kind of run the same playbook. And a lot of lead leaders I'm talking to now, it's like, hey, if they tried to solve this problem in the past or do we have to educate them completely? Right. And there's almost two different sales playbooks. So I'm just curious, what led you to kind of that realization to make the bifurcation and what does that mean as you're organizing your sales efforts, determining who to spend time with, how much can you gather from the outside? Right. Versus you have to have a conversation to know that this is a really interesting thread to pull on.
Andrew Berger [00:23:31]:
Yeah, for sure. So I think to set the framework a little bit, we're a financing business and so we have a portfolio, we have portfolio yield that we want to strive for. And in the portfolio there's diversifications. And so there's diversifications of how much, I guess I would say how much margin we're making on a, either per vendor level or a per program level. And so when we look at this bifurcation, what we've noticed is that kind of like the, the tech trend, which is we see a category called equipment financing. It's pen and paper, takes a very long time to get to respond to folks. People are frustrated, buyers are frustrated, vendors and sellers want to close deals faster. They're frustrated.
Andrew Berger [00:24:11]:
It can take up to 14 to 28 days. And if we can automate that and provide some amazing UX and ui, we're starting to see folks come to us directly. What we're striving for is volume. And we're going to go figure out the margins later. However, we have to be conscious of it because we have standard rates and then we know if they're already using financing, there's some sort of wiggle room that we understand the market is demanding. So I would say it's more of an effort of us being cognizant of who we're going to go after because we have to take it a few steps further. What is our portfolio going to look like? You could have a diversified portfolio, some high margin, some low margin, some medium margin. We don't want to lose any money on any contract that we're financing.
Andrew Berger [00:24:53]:
But I'd say the playbooks and you call them competitors, but who are the existing players in our market? Where do they sit? How do they interact with their customers? What conferences do they go to? Like we've never gone to equipment financing conference, but guess what, our CEO, CEO are just going as attendees next week to Chicago. Like those are new motions for us versus your traditional here's what an SMB customer looks like, here's what mid market looks like, here's what enterprise looks like. And I think that is now matriculating into what type of messaging. If you go to our website, we kind of go between buy now, pay later for SaaS or flexible payments. But people that use financing, it's called subscription financing, it's not called flexible payments. And so like even words matter, language matters. When you're trying to resonate with that director of revenue accounting who uses an existing program, you have to match what language they're using.
Todd Busler [00:25:40]:
So how do you take that? So it sounds like to me you, you've had some of these learnings, right? I agree that if you're in an industry or they're used to some existing terminology, like you don't even get a seat at the table if you're not using it. Right. But how do you go and begin to structure the team? Right? Because you're making a serious bets. When it talks about outbound, you only have so many hours or kind of arrows. How do you determine that? Do you say, hey, I'm putting 20% of the effort here. I'm going to let the founders see if there's something in this more experimental thing before we put headcount there. Like you're one of the stronger ops minds, but like, how do you think about it? How do you approach it? How do you allocate your team?
Andrew Berger [00:26:17]:
I will give you like an example and then I'll give into how we're thinking about it. Right now and everything's subject to change. We might learn something new tomorrow. They've throw this all out the door and I think that's part of, part of the game is have to be malleable and learn trends and pattern matching. I remember one of my leaders, Mike Cassetta, used to say like your job as a senior sales leader is to see around the bend for like the next two to three quarters, CEOs next five years, but you need to look around the bend for the next year. And so I think if you're really stagnant in how you operate today like that, you're going to come smack in the face pretty hard and you're not going to be able to adjust. But kind of getting back on track. What we are looking at and recognizing just a data example is that we have a contract you have to sign, but we don't really count you as a closed one opportunity unless we finance one of your customers contracts.
Andrew Berger [00:27:06]:
That's kind of how we operate. The company captures had a bunch of customers that signed contracts last year, but we were kind of slow to get them implemented. Call that like in the onboarding phase. Like we were stuck. Like great, MSA is signed, we haven't done a deal yet. What we've noticed is that folks were bringing them into the market, we're educating them into the market have a significantly longer you want to call implementation window or time to activate. Folks already in market and in industry we're talking about implementing like activating within two days. So I want to have a diversified pipeline that we have.
Andrew Berger [00:27:41]:
Some that's taken a while, but we see a huge opportunity. Some are pretty quick. And so how I think about that moving forward is I wish, you know, we had a pipeline problem solved where we're not in the business of having like every problem solved. So we're going after everybody like in those segments. But we're prioritizing and recognizing the learnings over the past six months to who are our tier one accounts? Here are tier two, here are tier threes. We had a huge mass outbound email program. Like we're talking like 20, 30,000 emails a month. And it was sophisticated, it was great email domains, high open rates, good sentiment.
Andrew Berger [00:28:14]:
We talked to a lot of people but it wasn't yielding really tangible results that we can get behind. So we recognize, all right, this market for this product, we have to change, we have to pivot. So we're now doing our typical like tier one, tier two, tier three accounts. I'm giving the reps the ability here's our accounts. You're going to pick 30 in your tier one, you're going to hell or high water, you're going to get an intro to that account. Tier 2 is probably a mixture of what we call like existing in market in Greenfield and Tier 3, our folks are, we're actually going to let our growth engine, they're going to go automate emails. Emails come from founders, email comes from coo. Emails come from me.
Andrew Berger [00:28:47]:
Part of me is kind of going back and forth into less prescriptiveness but more expectation setting with our team in terms of like I don't care if you make four emails on this account and then five calls or you switch it up like, you know, on average you got to make X number of contacts over 30 days before that account like moves back to being recycled. And so I'd say those are the learnings that we're taking. I don't have the biggest team. We're pretty small crew. We all work hand in hand together. We're in the trenches together. It's fun and we share learnings pretty synchronously across the group because we might have a sequence that's going. We're just going to completely change as we learn more market information.
Todd Busler [00:29:23]:
Probably when you were at the front or just after square, it was like cool. You could do some magical things with sales loft and outreach and like response rates through the roof. And it was kind of test and it was guaranteed to work. It was just what first find it. Now you can have some of the smartest people on a whole other scale and it's still like it's really challenging. So when you think about the success of the prospecting motion, right. And I know you bring that rigor into the organization, is it, hey, you better be able to break into X percent of your tier ones this quarter. Is it? I want to see two new business meetings a week.
Todd Busler [00:29:52]:
Like what are you rallying everyone around toward? And I think the metric is important, but I want to know kind of how you arrived at that. Right?
Andrew Berger [00:29:59]:
Yeah. Yeah. So for me it's all about new business meetings. And the reason why I serve a new business meeting is, is we can control that. We have about a year of data that shows meetings that lead to opportunities. The opportunity life cycle, close one activation. I'm kind of rallying the team around the winning by design bowtie model because our business is consumption. I mean that's really what it is at the end of the day.
Andrew Berger [00:30:22]:
And so of course want new opportunities that we're winning all the time going back to everything at square, like we held one metric consistent. Everything else, like we would kind of waterfall down and see the results. If we can increase the number of new business meetings per week, we put a rallying cry. We want to be at 20 new business meetings per week. That's where we want to be. That's our goal. Everything else will be taken care of. The model for the rest of the year, the financial model, the results, everything else consistent.
Andrew Berger [00:30:48]:
We get to 20 per week. We're in a great spot. When I came in in September, October, we were like 1 to 2. We're now like 5 to 8. And by next month we should be 9 to 12. And if I can see 10% growth every single month, by the middle of the summertime, if we're getting close to 14 to 15, I feel like we're on a great path. And it's like I've rallied the company around. There's one metric that matters.
Andrew Berger [00:31:10]:
20 new business meetings per week.
Todd Busler [00:31:11]:
I love that we think very similarly too. Like I think earlier in my career it was, you always think, oh, we have a win rate problem, we have a velocity problem. At the end of the day, they're usually misdiagnosed. Like Sam Blonde always says this quote as pipeline problems. And like you're can control. Can I find a way to get into this account and at least be able to introduce ourself? And you can control that if you're doing the targeting right, Learning and the targeting, everything will kind of work itself out.
Andrew Berger [00:31:36]:
Exactly, exactly. Because like every new conversation is a learning mechanism.
Todd Busler [00:31:40]:
100%. The pitch gets a little better, your objection gets a little better. You have one more case study because now you have a couple more happy customers and it all builds on itself.
Andrew Berger [00:31:49]:
Oh, I was, I was on a call last week and it's like, we have a really awesome potential new business opportunity for a company that's looking to go public. They want references. Have we really done references? Not really. But now the relationships that I've built with some of our existing clients leads us to have the ability to have personal connections and references. And now they're referring us to other folks. And like all of a sudden the engine starts to snowball. We're not there yet, but we're getting pretty close.
Todd Busler [00:32:16]:
Last question I have for you, Bergen, by the way, I think this, your journey is fascinating and admirable of just like, you know, you've done it during the highs of SaaS and kind of had some really good runs. And then, you know, it's Hard now, like people like me and you that I would bet on versus a lot of people, like, it's still hard. I run this podcast and I do webinars and stuff to explain to people. I don't have all the answers. And if someone says out they have all the answers, they don't because everyone's trying to figure this stuff out too. What advice do you have now that you've been this, you know, head of sales, vp, sales head of revenue leader multiple times? Like, what advice do you have for the first, the person stepping into that role for the first time where like, look, whether they like it or not, they're going to walk into some uncertainty, they're going to walk into some shit that isn't really working. What advice do you have now, now that you're on your, you know, fourth run at it?
Andrew Berger [00:33:04]:
I think the most critical thing, I think Jason Lum talks a lot about it is like, you got to be in the trenches. And I think Zerp era created some like ivory tower mechanisms. I fall right into that category. I was like, I have this team doing all the work. I'm just going to like manage my dashboards and all that stuff. And that did not work. What worked for me at Square was I could demo the product, my eyes closed. What worked for me at Front to the beginning of the day is I'd sit next to Mathilde calling and I would cold call customers, selling Front with her because I needed to learn.
Andrew Berger [00:33:35]:
I had to go close my own deals and kind of coming full circle. I'm on a much smaller team now at Capchase, which is great. Like we're being efficient before this call. I'm not kidding. I'm working with our data engineers and he's helping with a prompt engineering exercise on an ROI calculator in Claude. Like I'm literally building an ROI calculator in Claude GPT, just like riffing on it because one of our customers needs that and doing that work, making the connections on LinkedIn, having the conversations, doing the multi threading. I firmly believe that I have to lead by example with the team. And you know, when I had five directors with different teams, solution, consulting, SDRs, AEs.
Andrew Berger [00:34:14]:
Like you get brought in for like the last negotiating conversation and like too far removed. And so I've talked to a bunch of folks who are stepping in their first time VP role or head of role or like player coach role. It's like number one advice, like sell, sell, sell. Because you not only get credibility with your team, you gain credibility with, with the executive leadership team, like, wow, you're. You're really doing this thing. Like, you can speak to the pains versus I can listen to all the gong calls all day long, which I do, or get the email summaries on the week. And it's like, that gets to one level. But having, like, the felt learned experience is a whole different credibility level for your team.
Andrew Berger [00:34:51]:
Like, they respect you more and then for the company because they also respect you more.
Todd Busler [00:34:56]:
Berger, this has been awesome. I think the three big takeaways for me is just like, I'm not surprised by this at all, but you continue to outwork people and just set the example of like, look, I'm in the boat with you. This is hard. We're figuring it out together. I'm not above any work. I'm not sitting here refreshing a dashboard. I love the rally cry around 20 new meetings. Like, super tangible.
Todd Busler [00:35:15]:
Everyone can get on it. Everyone feels they have to play their part. And you're constantly chipping away. Like, I haven't met many leaders in the last couple of years that are like, wow, we found this one campaign and now we're skyrocketing. If you do, it's probably going to end in 30 days.
Andrew Berger [00:35:28]:
Tell us. Tell me.
Todd Busler [00:35:29]:
Yeah, or tell me, too. You got to find a new one. And the reality is, like, like you said, one of your leaders said, you're trying to see around corners and say, when is something going to break? All right, let's start fixing that now. And I just really respect how you've gone about it, so I appreciate you sharing some of the learnings. I'm rooting for you anywhere people can follow you or if they want to get in touch.
Andrew Berger [00:35:49]:
LinkedIn And then on Twitter or X, I literally just repost sports stuff. So not much going on over there. It's all San Francisco barrier sports, but LinkedIn hit me up anytime.
Todd Busler [00:35:58]:
Love it. Yeah, I'm sure there's a lot of people that are in the position you were four, five, six years ago trying to figure that out. And I think you have a lot of good battle wounds to show for what you've got. So, Andrew, big thanks. Good to see you, brother.
Andrew Berger [00:36:10]:
Thanks, Bus. Good luck out there.
Todd Busler [00:36:12]:
Thank 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.