YouSaid · the spoken record

Matt Plank

lines on the record: 76
first: 2024-12-20
most recent: 2024-12-20
sittings or episodes: 1
sources: podcast

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“I mean, honestly, I think for us, it's more of like a macro strategy of like breaking up our sales org, right? Like at one point, we had reps who sold all of the products of Rippling and when we finally got to a point where we launched our spend management suite. And I had a rep who had their 12th product that was competing against like a rep at ramp or brex where like all they sold was that very specific thing and just asking my rep to like be able to compete with that rep when they had 12 other products they needed to sell it just became clear that like there's the cup is too full here like we can't put more knowledge in like the sales rep, you know, cup and we need to basically carve off this kind of product account executive model and then build this like you know culture of like partnership and those deals so that when you are a new logo and you want to buy hcm stuff and spend stuff like you know there's two people working together and we kind of splintered that off now in a bunch of different places and had we not done that we never would have been able to compete”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You really should work for a CEO whose ambition and expectations make you deeply, deeply uncomfortable. The best coaches in the world, right? Like they're not your best friend. Like they coach you and they're like, you know, if you look at the whatever, all the different people, the Nick Sabans, the Bill Belichicks of the world, right? You have to want to work for someone that demands greatness every day often is completely unreasonable, like feels like is unfair and all this stuff, like you're going to get more out of yourself by working for someone like that than you would ever possibly get by thinking you can push yourself, you know, that hard. And so for me, it's like, don't work for a company because you think it's chill or it's easier. Like the CEO gets it and like they're not, you know, a huge go-to-market. They're not going to bust your, you know, ass all the time to go to market. It's like work for someone who you kind of walk out of there and they're like, man, that guy was intense. Like, I don't know, or woman was intense. Like, I don't know.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, candidly, I really miss the days of being the vibe that's in a company when like you're all in there on the same days and whatever. I think having said that, I mean, we are like, if you're in an office for us anywhere in the country, like you have to be in the office three days a week, but we do have people that we've hired remote across the world, really. And, you know, we have access to better talent, all that. So I think the remote people are part of the company culture. But yeah, I mean, if I could wave my magic wand and keep the people I have and force them to come to an office, like I would do it in a heartbeat. I believe that we've lost something over the years of not having the same company culture of an office.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I think more so now than ever, like working your ass off and hustling is like has always been able to get you ahead, but there was a culture pre-COVID where that was like table stakes and what everybody did and you were in the office all the time and you showed up at eight and you left at six and it was just like everybody did that. It was obvious and I think over time now the true like I just like and it's not like I work on the weekends and I work all night. It's like when I'm like in the walls of like the arena I'm like million miles an hour grinding, just like working my ass off as fast as possible to just like do more output. I think that is like less common than it used to be or is more of a advantage than maybe it once was”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, I guess maybe when I think about competitor, I respect the most, I think of it mostly from like a go-to market team perspective. And so I think like when we lose to a legacy payroll provider, I'm kind of like, damn, we got outsold. I know our product is better than payosity or ADP or whatever. And so when we, you know, when we're in a competitive deal and it's neck and neck and I'm just like, man, like they must be doing something good on the go-to-market front to make up for all of the like horrible blemishes that exist under the surface of that product when you actually use it.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I think maybe I would say probably in the HDM space, maybe like pelocity is of the legacy competitors, like they generally seem to be people we see in most of the deals. They do a good job, I think, of selling around their product apps, potentially. There's other players in our product suites at one point.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Then, like, I'm gone. Everybody knows that, right? If your manager, your team isn't your quota, it's like everybody feels that performance culture, but there can be a moment where you get so high up in an org chart that people start to feel like, you know, when things are failing, like nobody blames the person that runs that thing, right? They blame everybody else. And that's a really bad place to be.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“It was around the time where kind of speaking to this, it was at a point in time where there were people that reported into me who had maybe lost a locker room a little bit or at least when anybody is questioning like, is my manager or my director or whatever, are they scaling with me, right? Like when anybody starts to question that, they immediately look to the CRO and they're like, what's the CRO going to do about it? Right. Like, is this person going to, you know, kind of let that fly because they know the person, they've been here for a while, whatever. And a lot of companies, like that's what happens. And so I think for me, like you first see with your own eyes, like there's a problem here, and I'm giving the feedback, but like it's not changing, but then you start to feel that like other people like see that. And if you don't take action very quickly when those things start to fester, then like that's how you can lose the locker room. Like people need to know that you're willing to just like every rep, right? Is like, if I don't hit my quota.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I think when someone is not scaling, there are two things. I think one is they end up becoming like they're leading from the back and not the front. And what I mean by that is they believed that their job now is to like tell people like what to do because they've done it, but like they don't believe their job anymore is to like do it for them, show them how to do it, be involved in like, you know, leading the way and being like, everybody follow me. And they just kind of hit a point where they like they kind of think that being a director or VP or whatever means that like all of a sudden you don't have to do that stuff anymore. And usually when that happens, they start to lose the locker room and like even if it's a winning team, like their team starts to not really like them, you know, it starts to fall apart and kind of find her from there. And you can't come back from someone who loses like an organic promotion who was amazing all the way through, but then they like lose the locker room because they think that that's not my job anymore. I think that's.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Promote a bunch of people, managers become directors, like all this stuff, right? I mean, you look across your 10, 15 leaders that you've built that are all homegrown and organic, right? You're a 10, 20 million, whatever. You haven't hired anybody from outside the company really. You know them so well and you're like, you convince yourself that they're not gaps and they're all going to scale.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, look, the first thing is, generally speaking, if you are successful on the whole journey, then there's only like one reason that you don't make it. Like if you're successful, it works and rippling has been fortunate to be successful. And like, yes, in some part, do I feel like I run sales and I own some of that? Yeah, but like we've been successful for a million other reasons that are not me, right? The product that we built, the marketing team we have, all these other things, right? But I think when you are winning, like the reason that you top out in some companies, right? Like they're winning, they're doing pretty well by all metrics, but then they're like, but we got to go hire like a CRO because this person is like, you know, we're doing great, but we just, they're not going to make it. 100% of the time is because you can't hire people that are better than you or overqualify. Like you can't hire people. And the biggest thing is you don't acknowledge the organic growth that you built. So for example, like when you grow early on, you're going to.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Think that's exactly right. I mean, in fact, I'll give you the perfect example when Parker started rippling, who's the first person he wanted to hire? Like it was Sam Blonde, right? He's like, I want to say him, come work here with me. And Sam was like, no, man, like, I can't, you know, I can't do it again. And I started, you know, Sam hired me as Xenophon's and I started there as the, you know, 25th in Pleasant Account Executive. And so I had kind of grown up in the underneath kind of like Sam at the org. And so when Parker was like, okay, like Sam's not the guy who's going to come start in the basement again for a second time four years later. He immediately went to like the tree. All right. Like, you know, what's Plank doing? What's Jameson doing who, you know, built gong for many years? And now works at Rippling. So he picked, like both of us were.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The same company, it's like an immediate signal that that person is good, right? Like you don't get promoted twice at high growth companies if you're not good. And when they've done it in a rapid succession, right, if it's like three years in this role, three years in that role, three years in this role, it's like, okay, that's good too. But there's nothing better than like one year, one year, one year. It's like that means you promoted them. They took on a bunch of new stuff. It was growing. Everything was broken. They didn't know how to do it. And boom, they solved it. And like now they're under the next role. And so I think you find people like that. They may top out at like their experience has only been a director of sales of a 20 person team or something. And it's like, you don't need more than that when you're building a company from scratch.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You want to hire for slope, right? Like you want to hire for how steep you think somebody is going to be able to kind of grow in scale. Like the number one thing that I look for, I think if you're looking for an early stage sales leader, there's a bunch of things that we could get into. But I think one of the things that stands out is you want somebody who has been like rapidly promoted at the same company two or more times. Like that ingredient And what I mean by that is like if you're an account executive for like a year and then you're a sales manager for like nine months and you're like a director of sales for like a year when you look at high growth companies that are just like growing super fast, right? Whatever all of the historical SaaS companies you might want to go look at, where should I hire someone who worked at a high growth company and you find somebody who was promoted multiple times? There are lots of people that get promoted once and it's a mistake, right? Like they're not good at being a manager. They want to be a manager or whatever. But when you find someone that's been promoted two times.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Build in a good go-to market leader that you trust will help you figure that out. They're part of that journey. And so I think you should hire a sales leader like very early on. You probably should have some customers that have paid you some money. But I think founder is way too long to hire a go-to-market. And I think they do that because they feel like they can't hire a good salesperson potentially without a bunch of traction.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You're a founder from day one. I first of all think you should hire salespeople way sooner than conventional wisdom. And there's a lot of salespeople that will tell you that that's not true. Like, hey, you're a founder. You got to make sure that you can sign customers up and you have product market fit. Like, don't hire this poor VP of sales to come in here who will never be successful because your product, blah, blah, blah, blah, blah, blah. I don't believe in any of that. I believe that, I mean, I started at Parker's house when there were four engineers literally in the basement of his house. Like there were no customers. There was no CRM. There was no anything like granted, like me and Parker had a relationship. And so what I have done that with a stranger, like probably not. But I knew that Parker was going to like build the right thing. And I knew that he needed me to help him figure out, like, one, like do the sales so that I could take that off his plate. But there was a trust there of like, as we're building stuff and you have constrained resources and engineering, like what is the most important thing to build first? Like, how do you sequence the things we need to?”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Buyer, you know what I mean? Like, he doesn't know how to transform his brilliant thought into like a consistent, repeatable sales playbook. He does not do that. Like, that's not his thing. And so he's involved in the direction, you know what I mean? Like, he gives a lot of feedback. He's, he's kind of like, this is what I think. But if I push back on him, you know, there's friction and it's good, like friction is good and that kind of stuff. But eventually he'll get to a point where he's like, okay, okay, okay, that makes sense. He'll start from a place of extreme pessimistic view like I think that's wrong. I think that's wrong. Here's why here's why. And then if you like defend the position and you convince him of why you think your way is the right way, eventually he'll just be like, okay, that makes sense. You convince me that that's better and you should do it that way.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Founders definitely should not create the playbook. And I would say that Parker is like exceptional, like go-to-market CEO. In fact, I think one of his strengths is that he really is the main product kind of roadmap guy. Like his vision, you know, his product vision is really strong. But on the go-to-market side, like that guy can sniff out bullshit from anywhere. Like he knows just like all the places to poke, all the weak spots, all the bruises. And so Parker is involved in go to market. Is this really working or are you like, you know, making it appear as though it is when it's not? Having said that, he doesn't, he would never want to like, you need to do it this way. Pitch people this way. And I think the reality is Founder Parker is the best at articulating why somebody should care about our product, like why they should want our product. Why did we build it this way? What is all, where are all the benefits of building it this way? There's no one that does that better than Parker, but he doesn't think like our”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“That's certainly a way to do it. I would say that we are pretty disciplined in the kind of finance function of rippling to like not, you know, get the cheap thrill and go sink a bunch of money into these markets. Because like the reality, it's not just that it's inefficient. It's that like we don't know exactly what works, right? Like it's not the same playbook. The growth playbook is not the same. And so yeah, you could think that you could convince yourself that you could spend inefficiently and of course it'll work because it works in the US. But like you also might just light a ton of money on fire and like your whole strategy just might not work at all for a long time, whatever. And so I think really the answer for us is like outbound has been the thing that we've been able to scale the most because all of the growth, demand gen stuff is expensive when you can't offset it with referrals and word of mouth, whatever. And so the outbound thing is working really well for us, but like you got to hire 20, 30, 40, 50 outbound SDRs. You got to ramp them. You got to train them. Like it just takes longer to ramp the.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, so a couple of things. One is it is working in the sense that the win rates are really good. You see these are really good. All that kind of stuff, what is scaling slower than you would like is pipeline generation and top And that's because no matter how much money we have, we could be sitting on a billion dollars of cash, like we are not going to go invest in top of funnel that is inefficient just to grow faster. Like that's just like our guardrails. There's a certain cat payback.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Extremely ripe for disruption. And I think we have a really strong product market fit. And then there's a bunch of other things where we do really well with multinational companies and all those markets.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I think one, all of the non US markets, like starting with Canada and for sure and Europe and APAC, like their HR software landscape is at least a decade behind where the US is. Like in the US, you have 10 plus like major public company payroll providers, right? Like there's just an enormous, you've got all these IT companies, like all the ramps and Brexit of the world. Like it's at a deeply competitive market. And when you go internationally, pretty much in every country, whether it's the UK or France or Germany or Australia, whatever, there's literally like two people at max that are in that space. And one of them is like a completely old archaic, like awful system. And one of them is like a brand new startup that's like modern and easy to use, but has like enormous issues kind of like supporting all the different various use cases, large companies, whatever. So there's just those markets are like extreme.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The portfolio into something that works. And so your growth is just like it's a little bit stunted if you want to grow efficiently. Like we don't get to grow in these markets the same way that early stage companies do who don't really care that much about being efficient. Like we do care about being efficient. And so there are kind of these, you know, guardrails that we have to operate within. And so that has made growth a little bit slower than it would have been.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“You enter a new market, everything is way more expensive. When you're an early stage company, efficiency doesn't really matter. Like you don't even have a business, right? Like it's not about how efficient are you. It's like you're just trying to win in any way possible and you're losing money and all that good stuff. As you get to be larger and you're, you know, our size, like all of a sudden, like efficiency is like the number one constraint. Like there are things that we could go do to win more business in places that we don't do because we couldn't do it efficiently and we're not trying to light money on fire. And so in the US market, there's all these other things. There's organic, there's brand, there's all this like free accrued benefit over time. And so you can afford to go pay money and do different things to acquire leads and more expensive ways. When you go internationally, like all you can do on day one, right? You can go put money in the LinkedIn machine or the Facebook machine or the review sites or whatever. And you can get demos, but like you don't have all of the easier, more free stuff to blend.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Thinking about Parker would probably say everything, but I think probably like international, to be honest, like an international, we have teams now go to market teams in Dublin selling into Europe. We've got a team in Sydney selling into kind of Australian market. There's a bunch of international teams in place where we feel like we have incredible product market fit. We're trying to crack the code of like, you know, you can't just like land in these places and run all the same playbooks and do all the same stuff. And so I think our growth internationally is like there could be explosive growth and there will be soon, but we're like still kind of tweaking the ingredients a little bit.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Fastest growing segment for sure is like our up market segment, like our, you know, we're moving up market very quickly and used to not compete with the workdays of the world and now that's where in a lot of deals with them. And so that piece of the business is, and if you're going to grow 60, 70, 80, 90% year over year at hundreds of millions of dollars, like you have to be able to have some things that are growing to 300%. Like that's the only way you'll maintain the growth rate. And so I'd say our upmarket teams are growing a lot faster.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“A tough question to ask because we have direct segments, channel segments, product segments. Like there's literally 50 segments. But like at the end of next year, my SMB mid-market and enterprise teams will all be like roughly the same size, probably like SMBs maybe 60 reps mid-markets, maybe 90 reps in enterprises, maybe, you know, 40-ish reps or something. But that's 150 reps and there's probably 300 reps across the board that are in different types of places. So it's kind of a mixed bag.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The longest time up until maybe two years ago, I did the pitch decks with our CMO, we'd be cranking away in the middle of the night, like working on the slides and then we roll out the pitch deck and I do the trainings and I do the script. And like when you're an early stage company that makes a lot of sense. And then all of a sudden you get five segments, 10 segments, 20 segments, and like you're no longer the expert about all of them. And so I definitely held on to that like way too long. Kind of being the like the number one person in the org who like knew the script and the pitch and the competitors. And two years ago I hired like my first kind of like layer of just like really kind of successful VPs underneath me. And then over time now it's like I literally don't even think about those things like as completely owned by the VP of S&B or the VP of Bin market or whatever. And I should have done that like a lot sooner because what happened was we would be doing deals or we'd be in we'd have we'd have a deck that sucked and I'd go look at it and I'd be like this deck is terrible like this is this”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I can like control my own destiny, where I'm not told I can't prospect, but let me do something. But then when you give them accounts, like without a whole bunch of structure and focus, they're not ever going to show up and do the like the way that you manage a rep doing outbound is not the same as the way you manage an SDR doing outbound.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I understand that belief, and I think that rippling definitely will, of course, get to some scale and like saturation of the market where that's kind of true. But I believe that it is like critical to avoid that as long as you possibly can. And the reason why is like we've done outbound in 15, 20 different segments. And every single time there's a funnel of like number of accounts you work, dials, emails, your call to connect rate, your connect the demo rate. Like there's this funnel that just if you put all the things in the top it just spits out demos every single time we look at a new SDR team somewhere in that funnel is broken. They're not doing enough of this, enough of that. They're like called to connect. Like there's always some part of it. And then you hammer it and you go fix it and you train on it. And then it turns green and like all of a sudden they spit out demos. And in my opinion, you can get an SDR org to do that way, way, way more effectively than you'll ever be able to get sales reps to do it. So sales reps, what they want is they're like, give me a book of accounts.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Up until literally 18 months ago, I'd say up until two years ago, up until two years ago, like the sales org, myself and like everyone that reported to me literally never once thought about generating an outbound demo or like even like it was 100% like demos pop up on your calendar like marketing does a bunch of stuff inbound SDRs schedule them and like you just sit on you know go show up and you do four or five calls a day and like that's all you do over time we got to this i mentioned this pinnacle point like two years ago where ak Ashley Kelly, we were like, oh my God, we have to do Outbound. We hired her. We like, you know, grew it from zero to 100, whatever. And like we started to weave into the culture, like, hey, like as a sales rep, like you should care about where your pipeline comes from, but they still don't own it. Like Outbound SDRs own the quota, like they schedule the demos. If you're a rapid rippling, you have zero actual prospecting targets. And so over time, it was like the wholesale, which is.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The sales order gloss. I didn't set the team up successfully. I screwed this up. You got to own it with the CEO. You got to own it with the people down below you. And I think weak or like insecure sales leaders will try to deflect blame to some other leader or the team or you train. It's like Parker told me once a long time ago, I think something that really stuck with me. He's like, you don't get any credit for knowing how to do something yourself. Like zero credit that you know how to do X, Y, and Z. But your job as a sales leader is to get everybody else to do that. And so like you can't stand there and have like my team didn't execute and be feeling like, dude, I told him exactly what to do. And like they didn't execute, you know what I mean? Like, it's not me. I got to get a new team or something. It's like your job is to make them execute. It's not to know what to do. You're the head of sales. Obviously, you should know what to do. That's table stakes.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“For you. Thank you so much for taking the time. I would greatly appreciate any feedback you could give me. I'm always looking to learn. By the way, like if anything ever changes, I hope that you're successful with XYZ vendor. But if anything ever changes, please just know that I'm here for you, blah, blah, blah, blah, blah. If you leave every single interaction with that type of mindset, I promise you you'll get stuff that bounces back that you never expected to bounce back. They'll come back in two months and they'll be like, hey, this competitor lied to us. The implementation's terrible. There's a bunch of shit that they don't do that they said they did. But you have to leave it like that. And so I think on one hand, you got to like make sure that you're not sour when you miss and morale. If you're mooping your head around and you're all frustrated and upset, like that doesn't do you any good. It's a waste of time. And I think as a sales leader, you've got to like own the mist. Like you can't play viewpoint fingers at people and that's the MO that you have as a leader. Like it sounds very cliche, but it's like you got to walk up there and be like.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I think two part question. I think the first thing is I really believe very deeply in a core thing that I had to learn over time. And one of the things going back to the beginning of our conversation, when you're like a deeply competitive person and you do like expect to win and you like really, really hate losing, I can definitely tell you of examples in the past where I like reacted poorly to someone that said no, right, or someone that it was just like, it made no sense to me in like my initial reaction was just like the wrong reaction, right? And it's very easy for even the best salespeople because they're generally like the most competitive can get like pissed off and react poorly in a deal. And I had to learn over time that like you have to literally like kill them with kindness. Like you have to make them when someone tells you no, it's like, hey, like, thank you so much for your time, you know, evaluating rippling. I know how busy you are. I'm sure doing all these evaluations was like a total time sucker.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“They want to make sure that they get a demo. And it's like there's no such thing as delaying a deal for those types of reasons. You're starting over from scratch. You might not know it, but you're starting over from scratch. And so time kills all deals. And so you really want to try to like get them in, not to like hit your quota so that you don't go on a pip or whatever. Like you want to get them in because over time, like if we push as a company 25 deals in a month, like for sure we're not closing those 25 deals in the next month, right? Like some percentage of them just do poof and evaporate. So, you know, there are good reasons, but like I'll tell you the worst reason, the legal team didn't get the review done. Nothing, nothing is more frustrating than somebody being like the legal, they're legal team, right? They didn't get the red lines done on time.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The first thing I think about is like what is the historical tendency of this rep because deals do push in sales all the time. As Parker would say, did it push or did it poof? You know, when I show up at the end of the month and I'm like, hey, like, you know, had a rough monk, like, but we had some really good deals push. He's like, ah, you know, I don't believe like every time you say that, they poof and they don't push, they never come back and blah, blah, blah, which is generally not true, but he's deep skepticism of that. And so, but you got to look at a rep. Like, does this rep normally close deals in this timeline and this deal did push? Then that's very different than someone who's a perennial, like my deals always push. And I think the thing you gotta, you got to help reps understand is like a deals that put like a lot of times reps will think that a deal that pushed because of this person left the company or a new person joined or a budget, you know, dried up or whatever, they convince themselves that like, hey, this is delayed. This is just delayed. Like this new person joined.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, generally, we're doing pipeline reviews with managers and rep in like a one-on-one setting usually. There are times where we do a pipeline review. They might be with like a manager and their team, but you can't sit around a 40% segment and do deal reviews, right? Like it won't be, it won't be time effective.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Where you can poke holes at them and they're trying to like prove to you why this is a solid deal and there's no friction there. They're like, hey, this is what my manager shows up to do.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“I'll pick like our, you know, let's call it our middle mid-market team who's kind of like in the middle. The main thing that you're looking for in a deal review is like salespeople by almost like definition or like optimistic. Oftentimes they like they get happy years and they hear things that they want to be true. They might be true, but they don't sometimes ask like the second, third layer question to figure out if it is true. And so for me, deal reviews are all about asking your repos that person report to were they there when they bought this system like, you know, a bunch of questions around who are they talking to? How did these decisions get made? What do they think the timeline is? Like you're trying to basically poke a hole in this perfect, if you're just sitting there in your rep is like, hey, here's the next step and here's who I'm talking to. And, you know, it's all good. And you're like, okay, great. It sounds good. Like let's go to the next one, which is what a lot of pipeline reviews look like. That's like zero helpful. You got to create a relationship with your rep.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Sign that contract on the 31st, the end of the quarter, whatever, is because you've built a relationship throughout the entire valuation of some trust. Like they feel they've agreed to do some things and they want to meet their part. But without that, then time-based discounts don't work for anybody and they're actually anti, you know, they're like, they really are counterproductive.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, then I lose some leverage in the negotiation. And so they'll be like, ah, this is next year, you know, Q1 or whatever. But you got to find out from people what are they looking to do and like build some trust up front. And then before you get to pricing, you have to make a little bit of pokes out there like, hey, if we can get some competitive pricing that's kind of based on a timeline, this timeline we talked about, does that seem like something that you'd be interested in and like get some buy-in from them? Because people do not sign contracts on the last day of the month because they're worried that their discount is going to go away. Like that's absolute bullshit. Like if you ever bought software and it's the 31st of the month and someone's like, you have this quarter end discount, it's extremely unlikely that if you come back on the third or the fourth, they're going to be like, no, I won't give you that price. It's like certainly there might be different price. You might have to go through whole cycle, whatever. But the reason that the majority of people like.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“First big mistake that people make around discounting is they offer a time-based discounts before they even understand if somebody can possibly move that fast, which is like a terrible experience both for like you because you have no leverage once you've like thrown it out there and then for the customer it just like it feels awkward. It doesn't make sense. So the first thing you have to do is understand from somebody up front like in the first call what is your ideal timeline and the way we talk about that is like, look, you're obviously evaluating rippling. You've described these pain points up front. Just assuming that you wave a magic wand and rippling literally solves every single one of those pain points that you have, what is your like ideal timeline of when you'd like to be up and running in a new system? Just like if you could add everything, every boss checked, your perfect scenario. What does that look like? And then when they tell you that, and like, look, a lot of buyers are honest about that. Some buyers don't. Some buyers know that when they're upfront, they're like, I don't want to tell the salesperson that I want to move quickly, right?”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“The way I think about it is like, you know, what is your commission rate on a new logo? And that could range anywhere from 10% to 30%, depending on, are you outbound? Are you inbound? What deal size, whatever? And so you want to make sure that the kicker you're paying on a deal isn't much more than like 10, 15% of the deal, right? So if your commission rate is 20%, then maybe you're giving them an extra like two to three percent kicker for a multi-year deal, but you can't make it that your commission rate is 20 and then you sell a multi-year deal and you get paid 40, right? Like that math doesn't work. And so it's generally, I'd say maybe 10, 15, 20 percent of the original contract, like the year one contract, like, or thinking of the commission rate, like that's the right way to think about it.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Multi years is really important. And we have multi-year deals and we incentivize our sales team to sell multi-year deals. So if you sell a one-year deal versus a three-year deal, like we'll give you like a kicker in the comp plan to sell a multi-year deal.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“First of all, I think the main thing here is you gotta continue to inch it up over time until that friction of like, hey, this is like, this is more expensive than I thought I would be. This is like outside of our budget. This is 100% more than our competitor to X the price of a competitor or whatever until you get people that are like, you know, walking away, then you haven't found the right amount of friction right when you get to that point. And again, you got to go up gradually because you never, ever, ever, ever want to like go back, right? You don't want to like raise them and then be like, oh, never mind. We're going to like lower our prices. Like that's bad. And we don't do this, by the way, on existing customers. Like as we inch price up over time, like our existing customers that bought early on, like we lock them in pretty much forever. But you have to find that friction. And I think you'll squeak out a lot more revenue by finding if you raise.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Time. I'll talk to you, you know, an early stage founder who's often a technical founder, who's a referral from one of our VCs or something. And they're like, hey, we have win rates that are like 60, 70%. We have an incredible go-to-market fit. It's so great. My first thing I always tell them is I'm like, that's not good. You don't want win rates that are 60, 70%. You're either not in enough deals, right? Like you're just way too narrow or your price is way too low. Like if you win 70% of deals, then like that's not good. That's a bad, or at least you could go much bigger, right? And so I think people don't raise price up until they get to a point where you're about to lose deals because like people think you're overpriced. And there's like”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think there's like an evolution in a few different phases. I think the first one is when you're a zero to one company, whatever, you're a million bucks, two million bucks, like early, early stage, like nothing matters. The only thing that matters is winning customers. It doesn't matter what they pay. It doesn't matter what their logo is. Like you need customers to validate that you can charge something for your product and that they'll buy it. And if you look at what we charged at Rippling in the early days versus now, like it's not even on the same chart. And so you need customers. I think founders make a mistake. They're trying to like maximize the revenue of one specific deal, which is crazy. It's like never, ever walk away from any deal, any price that's not free. Like you sign them up, right? The big mistake that people make as they transition to the next phase, whether at maybe 5, 10, they're going to 20 million is people don't increase price into a point where they find friction, right? And so you need like friction around price is good. And so to your question earlier, like I get this all the time.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“As long as you can walk through the policy and stand behind it, then I think you're good. But you can't have wild, wild west where people just make up whatever price they want or else that it can get out of control pretty quickly.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, I think a couple things. So one is we have like an extremely consistent and firm like discount policy. So it's not like a rep can just, you know, make up whatever they want to do. And so we'll telephone when they come in, like, hey, here's what pricing looks like on a one-year deal versus a three-year deal, or like depending on your timeline or depending on the amount of products that you buy, right? And so for us, you could come in and buy three products in a week or you could come in and buy 10 products and take six months. And so there's a bunch of different like, there's probably five different levels of how big are you, what are you buying, what's the timeline look like, you know, all these different things. And this happens. Like people definitely talk in the market. And, you know, we've got 20,000 plus customers. And so for sure, people are talking and comparing invoices and whatever. But if somebody were to come back to us, which has happened before and been like, hey, well, this is bullshit. I like that someone's quoted rippling and I got different prices than you. And when I walked them through like, hey, look, here's like, you might think these things are the same, but they're a little bit different.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source
“So let's say that your list price, meaning when you show up and you send, I mean, look, starting all the way with like some companies have a price on their website, right? If you're very SMB and down market and you have a bunch of like self-serve signups and trials and all that, you basically need to have like a price on your website where someone can see it and sign up, whatever. That's not our business. Like for us, we are generally getting something on a call, understanding what their pain points are, what products are they interested in because we have 30. And so for us, you know, we have a list price, meaning there's a book price for every SKU that we have. So let's say it's $10 pepp and for a random skew. But like the actual price point that we're trying to target might be, you know, $8 or $7 or $6. It depends on the size of the company. If you come in and you're 50 employees and you want to sign up in one week, like I've got a little bit more room to make that happen if you're, you know, if you're 50 employees and you want to evaluate for three months, then it might be.”
2024-12-20 · The Twenty Minute VC · 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank · IDENTIFIED FROM THE TRANSCRIPT · source