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Matt Plank

๐Ÿ‘ค Speaker
645 total appearances

Appearances Over Time

Podcast Appearances

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

I mean, generally we're doing pipeline reviews with like, you know, 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 person segment and do deal reviews, right? Like it won't be, it won't be time effective.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

The first thing I think about is like, what is the historical tendency of like 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 month, like, but we had some really good deals push.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

The first thing I think about is like, what is the historical tendency of like 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 month, like, but we had some really good deals push.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

The first thing I think about is like, what is the historical tendency of like 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 month, like, but we had some really good deals push.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 a deep skepticism of that. And so, but you got to look at a rep. Does this rep normally close deals in this timeline and this deal did push?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 a deep skepticism of that. And so, but you got to look at a rep. Does this rep normally close deals in this timeline and this deal did push?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 a deep skepticism of that. And so, but you got to look at a rep. Does this rep normally close deals in this timeline and this deal did push?

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

Then that's very different than someone who's a perennial, like my deals always push. And I think the thing you got to help reps understand is 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 dried up or whatever, they convince themselves that like, hey, this is delayed. This is just delayed.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

Then that's very different than someone who's a perennial, like my deals always push. And I think the thing you got to help reps understand is 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 dried up or whatever, they convince themselves that like, hey, this is delayed. This is just delayed.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

Then that's very different than someone who's a perennial, like my deals always push. And I think the thing you got to help reps understand is 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 dried up or whatever, they convince themselves that like, hey, this is delayed. This is just delayed.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

This new person joined and they want to make sure that they get a demo. And it's like, there's no such thing as like delaying a deal for like those types of reasons. Like you're starting over from scratch. You might not know it, but you're starting over from scratch. And so time kills all deals.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

This new person joined and they want to make sure that they get a demo. And it's like, there's no such thing as like delaying a deal for like those types of reasons. Like you're starting over from scratch. You might not know it, but you're starting over from scratch. And so time kills all deals.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

This new person joined and they want to make sure that they get a demo. And it's like, there's no such thing as like delaying a deal for like those types of reasons. Like you're starting over from scratch. You might not know it, but you're starting over from scratch. And so time kills all deals.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 is more frustrating than somebody being like the legal, their legal team, right? They didn't get the red lines done on time.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 is more frustrating than somebody being like the legal, their legal team, right? They didn't get the red lines done on time.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 is more frustrating than somebody being like the legal, their legal team, right? They didn't get the red lines done on time.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

Well, I think it depends on so when you went first of all, for me, when a deal pushes, what that fundamentally means is that like you forecasted it to come in, like you said it was going to come in and it didn't come in. And so if you if telling us and rolling a deal up that, hey, this deal is definitely coming in, like they just need to get red line sign.