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

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“So, first of all, discounting is a completely like made up thing. Like at the end of the day, the only thing that matters is like net price, right? And so discounting is simply a factor of like where do you set your list price? Like list price doesn't matter, right? Like net price. So if you set you discount 50% off or you discount 25% off, like it's all relative to whatever your list price is, which for most people is like a fake price. Like nobody cares about list price. They care about net price. And so I'm a big believer.”
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 also have to do both. So, when we first launched account managers, they only had a new revenue quota. So the 100% of their focus and comp plan was tied to selling new products. They cared about retention, but like they didn't own a retention number. And, you know, when your high velocity, a little bit more down market, there was just a belief that like, you know, they would care and do the right things, but like you didn't need to incentivize them. And then we did that for like, you know, nine, 12 months, and we quickly realized, okay, this doesn't make sense. And this year actually, we changed the compliance. I think like 70% of it is tied to selling new business and 30% roughly is tied to retention specifically, like dollar retention. And it completely changed everything in our have just like completely outlier like off the charts low churn metrics. And so they got to own new revenue and churn absolutely has to happen. Can't do it any other 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
“Because our sales reps are very high velocity. They're doing a lot of calls and they're focused on if a new logo deal is $45,000, like an add-on contract for someone that signed up six months ago might be $5,000 or something. And so their calendar is stacked up with deals that are $40,000, $50,000, $60K. And then all of a sudden you throw this meeting on their calendar for a $5,000 deal, they're just not going to be able to give it the attention that it needs. And so we split the team and we changed the function. We said, look, we need like account management. We need people who have had sales carried a quota, want to be held accountable to quota and all that kind of stuff. And so at Ripling, we have new logo sales reps, you know, pass a deal over the fence, and then they have account managers who own the commercial relationship renewals. They still own success, like unsuccessful companies will not buy anything new from you, obviously. And so they do have to make them success.”
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 in terms of customer success, like at Rippling in the very early days, we had customer success, which I think of as like their, you know, charter is make customer successful, renew them, but like it's not to, you know, it's generally not to like sell new products. And so early on at Rippling, again, we had three products when the company first launched, and now we have over 30. And so at Rippling, early on, we had customer success. And when somebody signed up for Rippling and then they came back six months later to add a product, like we would bring it back to the original sales rep. And like over time, that was just like clearly a terrible model. And so we converted 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
“In our mid market segment, where we have a $45,000 average deal size, it's probably 50 days. Like you'll get deals that come in and, you know, a month at the right time of year. And then you'll get deals that take three, four, five months on the longest end. But on average, it's probably 50, 60 days in our mid-market segment. There's not a lot of companies closing 45,000 dollar deals in 60 days. Like that's a very uncommon kind of, you know, funnel.”
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 it's a good point. So when we don't do outbound for those type of companies, that team is 100% an inbound team. We do outbound in our mid-market segment, which is essentially 50 to call a 250 employees. And then we do enterprise air quotes from like 250 to 1,000. And then we have a team that works from 1,000 to 5,000 person companies. Now, one of the benefits of rippling is when you buy rippling, you're buying a seat for like every single person in the company. So like a lot of products, if you're buying Confluence or something, right? You get a seat for everybody, but it's like $10 PEPM, right? If you're selling Salesforce, it might be $100 PEPM, but like you're only getting, you know, five seats and a 50% company, right? We are fortunate that you, everybody at Rippling, you know, you're getting a seed for everybody in our average PEPM is like $60,000 PEPM across the customer base. So for our mid-market segment, selling the companies 50 to 250 employees, the average deal size is like 45K. And so 45K, you can easily build.”
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
“Sorry, yeah. So mid market is probably around 20-ish percents. And then I think enterprise is maybe closer to like 15%. And I think the way you think of the way I think about this is it really depends on what you measure, right? And so for us, like if you schedule a demo and somebody like takes the call and basically says like, yes, I would like a follow-up email. Like, you know, we don't go through like, do you have a budget and what's your timeline? We do that in a sense in the evaluation, but we're not incredibly strict about like who do we bring into the pipeline. And so when we convert a demo, we call it stage two and s two. We measure win rate like from s to, you know, all the way to a one deal, but that's going to be like a penalizing kind of win rate if you've converted something to stage three. That means like they've engaged in like scheduling a second call, right? Like they actually have some commitment to like do a proper valuation. And if you measure win rates from like stage three to win, then like you actually have”
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
“Count executive team. So you have a core rep that brings you know, sells the majority of the HR stuff. Then you've got like a different finance suite rep. You've got a global suite rep. And so that's how you end up with like 50 segments when you're kind of when you end up with a product suite that's 30 plus products.”
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, we sell the companies as small as three or four employee founders running payroll for the first time, right? And so on the very low end of that market, you know, we win 50, 60% of the opportunities. And honestly, the majority of the ones we don't win, they're just like, you know, funding fell through or whatever. They don't need to run payroll anymore for some reason. And on the high end of the market, we're selling to companies that are up to about 5,000 employees. It really has a wide range of the different segmentations. Now for us, we have segments that are based off of employee size like any traditional company. But then we also have a bunch of products that like our core new logo reps sell. But then we have too many products. We've got like 30 different products at Ripling. And so as we started the spin off different product suites, like we launched a finance suite to compete with your Brexas and your ramps of the world. We launched a global payroll suite to compete with your deals and remotes by global. And so at some point, we had to carve off like a separate what we call product.”
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
“And you basically ladder up, and you kind of ignore the number. Like, you're not focused on the number that someone asked you to get to. You start from a place of if I just make reasonable assumptions about growth and all these different things, like what does that get me to? And then generally there's like the plan that you believe is attainable. And then there's like the plan that you want to get to and there's a gap there. And then you go through this exercise of like, how are we going to plug that gap? Like what are the 10 or 15 different levers that we could pull this year to be able to close that gap? And for us.”
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
“There's two different ways that I think you think about a plan, and for us historically, we start with usually something that Parker is like, hey, if we want to continue to be in the top 1% of SaaS companies out there, this is a number that we need to go get next year. This is the growth rate that we need. This is what we need to hit to continue to be like, you know, an outlier in the market. And you look at that number and you're generally like, wow, that's definitely not an easy number to go hit. Otherwise, like, of course, why would it be an outlier? But then you go through like a ruthless, detailed planning process for us at Ripling, we have 50 different sub-segments, right? So you have, you know, SMB and mid-market and enterprise and channel sales and product sales and all the different products. And so if you think about there's like 50 capacity plans in a spreadsheet, and it's like how many demos are we going to generate? How many reps are we going to hire? Like what are their quota? And you go through that in great detail through all of the different teams.”
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 their goals are how much pipeline do you generate? That's all we talk about in our forecast meetings. That's what they're geared around. And so I think culturally you have to have it be that way from the top down.”
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, it comes from the culture of the org and generally from the CEO, right? Like if I show up to a meeting with Parker and I'm like, hey, we're going to massively whiff revenue this month, but like it's all marketing's fault, you know, like they didn't generate the demos they said they were able to giggle at like the idea of that, right? Like that would absolutely never fly, right? Like that conversation wouldn't be able to happen. And so you can't like blame marketing when you miss the plan because it's like, so what? Like we have a plan. What are you going to do about it? And you can't take all the credit for yourself when you build an outbound org and all of a sudden the pipeline splits and you've got 50 50 or whatever you have to acknowledge and give marketing credit. And while they're not incentivized from like a comp perspective, it's like deeply built into the culture that like our marketing team has a pipeline plan that they sign up for. They don't have like a, you know, how many, you know, webinars did you do and how many content downloads did you get? Like those things are important.”
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
“But we just have this incredible cross functional partnership. And so what marketing is goal in Hellbound is they are telling us essentially like who should we reach out to and when and they're doing that by capturing all this like intense over the internet, right? Who's on our website, who's on our review sites, who just recently changed a job on LinkedIn. And so they're curating like intent across all of our accounts that we would want to go after. And they're teaming it up for us. Hey, this person, you should reach out to right now. And then they, of course, help with like the messaging, right? Like here's the most effective sequences. Like they help us with the cold call scripts. And so the SDR work has an opinion on all of those things. And we're responsible for ruthless execution of a very daily driven KPI business. But marketing is absolutely critical in making it work. And if you don't have a really strong partnership,”
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
“There's really two things that are important. I think the first is you have to have a very deep partnership with marketing where you don't care about like credit. So for example, when marketing shows up and they generate 100% of the pipeline and it's all inbound demand gen, you know, form fills, hand raisers, and they're flowing to your inbound team, when you start to spin up outbound, you're trying to create a new incremental pipeline, right? Like if you obviously hire 100 SDRs and you end up with the same demos you had when you had inbound, like that's obviously a bad equation, right? Way more cost and like no more pipeline. And so marketing, you have to have such a partnership with them where a lot of the stuff that marketing does, it drives outbound success, right? And so when you schedule outbound demos, like you've got to also give marketing credit where credit's due. And I think a lot of companies, they break that. And a lot of times they'll have marketing in, you know, different orgs and sales, which is true at Rippling as well. Marketing does not roll into me.”
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 plan for next year, and we looked at what the growth rate needed to be in marketing was kind of like hey, we can't grow form fills by that percentage. It's like there's no way. And we had to like very, very quickly build an outbound org from scratch overnight. It was super stressful. And I wish we would have done it much earlier, but there's no way to grow and scale a big company without doing HalPound. So it's harder and it's different. But to say that it's dead, I think, is insane. I mean, we book 50% of our Outbound demos. We book over the phone. So we schedule like a thousand outbound demos a month. in our SDR work and literally half of them are booked over the phone. And so anyone who says it's dead, I think, just doesn't know how to do it effectively.”
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 people that say Outbound is dead are either one of two things. Like they're either engagement baiting, you know, looking for a reaction on LinkedIn or whatever. They know that there's a whole army of people out there where that's their profession and they're trying to kind of create, you know, whatever some conversation around it or they're generally not good or having their own something of large scale. I mean, to even claim that Outbound is dead, it's just absurd. It's like what else would you build a business if you think you can rely on marketing form fills or marketing programmatic email or whatever, it just means that you've never scaled something. In fact, I'll tell you that in the early days of Rippling, one of the great mistakes is that I didn't push outbound harder. Like the marketing team at Rippling was absolutely one of a kind. They generated thousands of inbound demos every month. And we got to a kind of crisis point throughout our journey where we looked.”
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
“People, they get a no from somebody and they just like abandoned. Sometimes in the worst case, they won't even respond. Hey, thank you so much for your time. Thank you for evaluating all that good stuff. But I'm over the top like kilomet of kindness when they say no. And that really just builds you this like big circle back kind of loop back pipeline that will help you, you know, in years down the road. Ma, is it easier to sell a product where you are replacing an existing line in a financial model or in an expanses page or budget? Or is it easier when you are a net new line item? I think it's way easier when you're replacing something, in my opinion. When you're trying to create a category or create budget for a thing that doesn't exist, there's just a whole bunch of different things that you have to go through. I have always, for the most part, sold the product where you're, I mean, I think early on, I guess, in the early days back with Sam Blonde when we were at an ECHO sign, you were saying.”
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 sure. I think someone not deciding, I in many cases mean that you didn't prove enough value in the solution you're selling or whatever it may be. But there are also just a lot of good reasons why, you know, someone's not ready for whatever reason or really like dynamics change in the company. A lot of time the person that you're evaluating with might leave the company or something they might hire someone new who now owns that decision. And so there's plenty of good reasons. And I actually think the way that you deal with that is really, really critical and like the best reps over their time and their tenure, they grow and they build a pool of those types of people. And as long as you have really good engagements with both the people that you win and also the people that you lose, they start to come back around. You just get this circle back loop of all these people that you've spoken with in the past 18 months. And a lot of times when they come in the second time, they're immediately ready. The deal cycle moves way faster. It's a lot easier. And so sometimes I think.”
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
“Lose a deal in most cases, at least at rippling, is indecision, people that are basically end up staying with whatever solution they have today. At least in our case, we are ripping in replacing something pretty much every time we bring on a new customer. And so the overwhelming majority, I mean, if you look at the pie chart of closed loss reasons, almost half of them are basically like unresponsive, right? Or maybe a third of them are unresponsive. Like literally you do a few calls and it's going well and they just completely ghost you. Some other big chunk of them are people who get back to you and are like, hey, we decided to hold off for now, you know, whatever, something in the company changed priorities budget. Someone left. And so there's a lot like if I think win rates are different if you think about a decision to deal, right? Like a deal where they decided to go with you or a competitor, then I think you'd look at win rates that are much higher in those cases. Indecision. Is that not just a sign that you haven't articulated the solution articulately enough?”
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 never feel it again. Yeah, well, I think look, like loving, winning and having like a deep hatred when you lose are kind of one in the same, in my opinion. And so as long as, you know, losing stings and motivates you and all of that. But I mean, if you think about in sales, I mean, even the best sales reps I know, depending on whatever segment you're in, their win rates are anywhere from 15, 20 percent, maybe 30, 40 percent at the absolute highest end. And so regardless, like every month, every quarter, you're losing the majority of the opportunities that you're in. So you got to be able to know how to, you know, lose an opportunity and come back and bounce back and, you know, focus on the wins and all that. So yeah, you got to be got to be okay with accepting a lot of rejection if you're in sales. Why a win rate so low, Matt? I'm an amateur. This show is brilliantly successful because I know very little. Why are win rates 15 to 20%? And you're just losing to competitors. You know, the number one reason why”
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 could think of there was a commission job. I was doing it from a pretty young age. Do you think that people all are born salespeople or do you think it's something that can be learned? I think there's a lot of people that are born that could be salespeople, you know, just given the kind of the attitude that you have. And I think there are certainly some people who are born who probably don't, you know, would like run in the opposite direction from any sales job. But I think it comes from wanting to be competitive and being okay when you lose because in sales, like, yes, of course, you win, but you lose the majority of the time really. And so I think there's a lot of dynamics that I think that you have to kind of have the right ingredients. But I think from there, you can certainly, you know, teach a lot of the skills that, you know, they make a good salesperson good. Do you think it's okay to be good with losing? Like, I fucking hate losing. I would kill my kids if they ever said that they were okay to lose. It should hurt every time in every way. And you should remember 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
“Excited for this dude. I've heard so many good things both from Ashley and from Parker. So, thank you so much for joining me, Stay Man. Yeah, absolutely. Thanks for having me. Likewise, I've heard a lot of great things and watched a lot of great episodes on the podcast. So excited to join you. Yeah, bribery goes a long way, dude. Listen, I think there's a moment when people fall in love with sales. Can you take me to when did you fall in love with sales and realize that this was the career for you? Candidly, I've been in love with sales since I was selling rapping paper in fifth grade and elementary school. And I think for me, it's always come from probably some part of competition, you know, wanting to sell stuff and kind of be number one on whatever leaderboard I was. And believe it or not, they get you primed for that in elementary school when you're selling wrapping paper or discount codes to your local stores or whatever. But then all the way through college, I was selling hot tubs and appliances at Sears and CutCoat knives and really anything you.”
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
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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
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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, 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. The big mistake that people make as they transition to the next phase is people don't increase price into a point where they find friction. This is 20 sales with me, Harry Stubbings. Now, 20 sales is the monthly show where we sit down with the best sales leaders in the world to discuss how they built a sales machine. And today we're joined by one of the best Rippling CRO Matt Planck. Matt joined Parker Conrad, Ripling's founder, when Ripling was just a V1 idea in a basement and had zero dollars in revenue. Today, the company has hundreds of millions of dollars in ARR and is a market leader. Prior to Rippling, Matt was a sales director at Xenophys, where he helped scale the company to $70 million in AR.”
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