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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

You have to want to work for someone that demands greatness every day, often is completely unreasonable, feels like is unfair and all this stuff. 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 that hard. And so for me, it's like, don't work for a company because you think it's it's chill or it's easier.

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 the CEO gets it and like, they're not, you know, a huge, like go to market. They're not going to bust your 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 a woman was intense. Like, I don't know. You know what I mean? That might be uncomfortable, 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 the CEO gets it and like, they're not, you know, a huge, like go to market. They're not going to bust your 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 a woman was intense. Like, I don't know. You know what I mean? That might be uncomfortable, 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 the CEO gets it and like, they're not, you know, a huge, like go to market. They're not going to bust your 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 a woman was intense. Like, I don't know. You know what I mean? That might be uncomfortable, 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 you should feel that when you're going to go work for a CEO.

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 you should feel that when you're going to go work for a CEO.

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 you should feel that when you're going to go work for a CEO.

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, 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 at Rippling.

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, 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 at Rippling.

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, 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 at Rippling.

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 when we finally got to a point where we launched our, you know, spend management suite and I had a rep who had like 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, 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

And when we finally got to a point where we launched our, you know, spend management suite and I had a rep who had like 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, 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

And when we finally got to a point where we launched our, you know, spend management suite and I had a rep who had like 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, 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

It just became clear that the cup is too full here. We can't put more knowledge in the sales rep cup. And we need to basically carve off this kind of product account executive model and then build this culture of partnership in those deals so that when you are a new logo and you want to buy HCM stuff and spend stuff, there's two people working together.

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

It just became clear that the cup is too full here. We can't put more knowledge in the sales rep cup. And we need to basically carve off this kind of product account executive model and then build this culture of partnership in those deals so that when you are a new logo and you want to buy HCM stuff and spend stuff, there's two people working together.

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

It just became clear that the cup is too full here. We can't put more knowledge in the sales rep cup. And we need to basically carve off this kind of product account executive model and then build this culture of partnership in those deals so that when you are a new logo and you want to buy HCM stuff and spend stuff, there's two people working together.

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 we kind of have splintered that off now in a bunch of different places. And had we not done that, we never would have been able to compete in these kind of like hyper competitive, like vertical spaces, like finance and global payroll.

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 we kind of have splintered that off now in a bunch of different places. And had we not done that, we never would have been able to compete in these kind of like hyper competitive, like vertical spaces, like finance and global payroll.

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 we kind of have splintered that off now in a bunch of different places. And had we not done that, we never would have been able to compete in these kind of like hyper competitive, like vertical spaces, like finance and global payroll.

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, you know, we've done a really good job in those spaces by being able to do that strategy, which is operationally very complex, but like my RevOps team kind of makes it, you know, takes it on and makes it happen.