Opinion
Plank: People calling outbound sales dead lack experience or seek clout
“I think people that say outbound is dead are either one of two things. Like they're either engagement bathing, you know, looking for a reaction on LinkedIn or whatever that they know that there's a whole army of people out there where that's their profession a…”
Insight
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…”
Insight
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.”
Insight
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…”
Disclosure
Plank: Rippling account executives have zero outbound prospecting targets
“Outbound SDRs own the quota. Like they schedule the demos. If you're a rep at Ripley and you have zero, like actual prospecting targets.”
What-if
Plank: Rippling couldn't compete in niche verticals without specialized reps
“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”
Insight
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.”
Disclosure
Rippling ties account manager compensation 70% to new business, 30% to retention
“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, you know, like, have just, like, out, completely outlier, like, off the charts, l…”
Insight
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 …”
Insight
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…”
Insight
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…”
Insight
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.”
Insight
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…”
Assertion Not checkable as stated
Plank: Non-US HR software markets lag the US by a decade
“All of the U S non U S markets, like starting with Canada and for sure in Europe and, you know, an APAC, like their HR software landscape is at least a decade behind where the U S is”
Prediction Not checkable as stated
Plank: Rippling will not fund inefficient top-of-funnel spend for growth
“No matter how much money we have, we could be sitting on a billion dollars of cash. Like we are not going to go invest in top of funnel that is inefficient just to grow faster.”
Insight
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…”
Insight
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 …”
Insight
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.”
Assertion Not checkable as stated
Plank: Top sales rep win rates max out at 30% to 40%
“Even the best sales reps I know, depending on whatever segment you're in, you know, their win rates are anywhere from 15, 20%, maybe 30, 40% of the absolute highest end.”
Assertion Not checkable as stated
Plank: Prospect indecision is the primary cause of lost sales at Rippling
“You know, the number one reason why you lose a deal in most cases, at least at rippling, is indecision.”
Insight
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.”
Disclosure
Rippling schedules 1,000 outbound demos monthly, half over the phone
“50% of our outbound demos we book over the phone. So we schedule like a thousand outbound demos a month in our SDR org, and literally half of them are booked over the phone.”
Disclosure
Rippling goals its marketing team on pipeline generated, not activity metrics
“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, but like their goals are how much pipeline do y…”
Assertion Not checkable as stated
Plank: Rippling's mid-market win rate is 20% and enterprise is 15%
“Mid market is probably around, you know, like 20 ish percents. And then I think enterprise is maybe closer to like 15%.”
