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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

But I think from there, you can certainly, you know, teach a lot of the skills that, you know, that make a good salesperson good. Do you think it's okay to be good with losing?

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

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, you know, their win rates are anywhere from

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

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, you know, their win rates are anywhere from

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

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, you know, their win rates are anywhere from

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

15, 20%, maybe 30, 40% of 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 lose an opportunity and come back and bounce back and focus on the wins and all that. So yeah, you got to be okay with accepting a lot of rejection if you're in sales.

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

15, 20%, maybe 30, 40% of 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 lose an opportunity and come back and bounce back and focus on the wins and all that. So yeah, you got to be okay with accepting a lot of rejection if you're in sales.

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

15, 20%, maybe 30, 40% of 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 lose an opportunity and come back and bounce back and focus on the wins and all that. So yeah, you got to be okay with accepting a lot of rejection if you're in sales.

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

You know, the number one reason why you lose a deal, in most cases, at least at Rippling, is indecision. People that basically end up staying with whatever solution they have today. At least in our case, You know, we are ripping and replacing something pretty much every time, you know, we bring on a new customer.

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

You know, the number one reason why you lose a deal, in most cases, at least at Rippling, is indecision. People that basically end up staying with whatever solution they have today. At least in our case, You know, we are ripping and replacing something pretty much every time, you know, we bring on a new customer.

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

You know, the number one reason why you lose a deal, in most cases, at least at Rippling, is indecision. People that basically end up staying with whatever solution they have today. At least in our case, You know, we are ripping and replacing something pretty much every time, you know, we bring on a new customer.

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 the overwhelming majority, I mean, if you look at the pie chart of closed loss reasons, you know, 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.

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 the overwhelming majority, I mean, if you look at the pie chart of closed loss reasons, you know, 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.

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 the overwhelming majority, I mean, if you look at the pie chart of closed loss reasons, you know, 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.

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

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?

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

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?

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

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?

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

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.

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

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.

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

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.

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

For sure. I think someone not deciding 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 someone's not ready for whatever reason or really dynamics change in the company.