The Ledger
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At $200M revenue, CRO role shifts from closing deals to sales operations
“By the time you get to be maybe, I don't know, two hundred million or something, like your job as the CRO, it completely changes to essentially like head of sales operations. Like you have a great sales operations team, but
At some point it transitions complet…”
Plank: Customer success managers cannot be turned into quota-carrying sales reps
“A sales DNA at the core is just, you can get those people to have like empathy for the customer and like understand and care about making them successful, but I don't think you can take a CSM and make them, you know, like a quota carrying rep.”
Plank: A 60-70% sales win rate indicates underpricing or narrow targeting
“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, r…”
Plank: Founders wait too long to hire GTM leadership
“Founders definitely should not create the playbook, but I think founders wait 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.”
Plank: Discounting is a made-up concept and list prices do not matter
“Discounting is a completely like made up thing. Like at the end of the day, what 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 …”
Plank: Early startups should never turn down any non-zero price deal
“I think the first one is when you're a, you know, 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 doe…”
Plank: Time-based discounts without trust are counterproductive in enterprise sales
“People do not sign contracts on the last day of the month because they're worried that their discount's gonna 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-e…”
Plank: Sales deals delayed by stakeholder or budget changes start over
“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.”
Efficiency does not matter for early startups, but becomes the top constraint
“When you're in an early stage company, like efficiency, like 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 any way possible and you're losing money and all tha…”
Plank: Post-COVID drops in baseline hustle make intense effort a larger advantage
“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 left at six. And i…”
Plank: Sales leaders should work for CEOs with uncomfortably high expectations
“I think more than anything Like you really should work for a CEO who's like, whose ambition and expectations make you deeply, deeply uncomfortable. Like that, that is, I think if you think about like, you know, some huge, like, you know, sports nerd, and it's …”
Plank: Scaling companies fail to raise prices until finding friction
“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.”
Plank: Replacing existing software budgets is easier than creating new categories
“I think it's way easier when you're replacing something. In my opinion when you're trying to create a category or you know, create budget for a thing that doesn't exist, there's just a whole bunch of different things that you have to go through.”
Plank: Multi-year sales kickers should equal 10-20% of year-one commission
“You want to make sure that the kicker you're paying on a deal isn't much more than like, you know, let's call it like 10, 15% of the deal, right? So maybe if you're, if your commission rate is 20%, then maybe you're giving them an extra like two to three perce…”
Plank: The main cause of legal deal delays is failing to parallel-track
“You have to parallel track those like legal things, budget review. You can't just like get a yes and then start all those processes over. And that's the number one reason why people push a deal, a committed deal because of legal review is like, they just didn'…”
Plank: Responding to lost sales deals with kindness yields unexpected win-backs
“If you leave every single interaction with that type of, like, mindset, I promise you, you'll get stuff that bounces back that you, like, never, like, expected to bounce back.”
Plank: Sales leaders get zero credit for personal execution ability
“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. Like your job as a sales leader is to get everybody else to do that.”
Sustaining high revenue growth requires individual business segments growing 200-300%
“If you're going to grow, you know, 6070, 80, 90% year over year at hundreds of millions of dollars, like you have to be able to have some things that are growing, you know, two, 300%. Like it's the only way you'll maintain the growth rate.”
Plank: Two rapid promotions at one firm signals a top sales hire
“But when you find someone that's been promoted two times at the same company, it's like an immediate signal that that person is good, right?”
Plank: Sales leaders fail to scale when they stop leading from the front
“When someone is not scaling I think 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're, they believe that their job now is to like tell people like what to do becau…”