The Ledger
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Grosser: Pure product-led growth stops working beyond Series B
“So at Stripe, as an example, product-led growth, sort of like the online self-search channel was awesome for, let's call it a series A, series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. P…”
Grosser: Great sales reps can run effective calls without deep product knowledge
“A savvy salesperson can talk to somebody actually knowing very little about the product they're selling because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls p…”
Grosser: Product managers pitch effectively because they own the product vision
“Products should be pretty darn good at pitching as well. It has a stronger point of view often on the vision because it's in their head.”
Grosser: Modern sales compensation structures are outdated 20-year-old relics
“I just think a lot of it is still a relic of how sales worked 20 years ago, and I think there's, like, a huge opportunity to be more innovative in the metrics, in the integration of cash and equity.”
Grosser: Stripe's internal tooling and systems haven't scaled with sales headcount
“Honestly, like, we're hyper growth, and I think our, the underlying tool systems operations haven't scaled as quickly as we've Scaled salespeople. Data, rigor, velocity, those all hold us back.”
Grosser: Founders wait too long to hire dedicated sales reps
“Sales is a skill, just like writing code is a skill. And so they often, I think, maybe hang on to that role as the initial salesperson, maybe a little bit too long before thinking about perhaps I want to bring in somebody who has good sales skills in this area…”
Grosser: Early startups should hire individual sellers before a Head of Sales
“I think you don't have to get your head of sales in at that moment. You know, you want to get probably a seller who's done it before, who has some amount, you know, enough experience that they can sort of be self-driven on this But I think it's hard sometimes …”
Grosser: Early startup sales is equal parts revenue generation and R&D
“Because I've always sort of said sales is one part revenue and one part R&D.”
Grosser: Founders underappreciate sales as a skill and hold it too long
“Founders underappreciate the fact that sales is a skill, just like writing code is a skill. And so they often, I think, maybe hang on to that role as the initial salesperson, maybe a little bit too long before thinking about perhaps I want to bring in somebody…”
Grosser: Founders should hire sales teams earlier than they anticipate
“I think bringing in a sales team often probably should have happened earlier than founders anticipate.”
Grosser: Hiring a Head of Sales too early is a startup mistake
“But I think it's hard sometimes to hire your head of sales at that point, because you may not ultimately know who you're going to wind up selling to as you get to more and more scale and different sales leaders spike in different areas. And so a mistake that f…”
Grosser: Startups should hire two to three initial reps to validate patterns
“You know, it's hard to trust a single individual's point of view on what the pattern is. And so I do think you're going to want two to three folks to sort of corroborate that pattern as being, you know, true versus sort of a single individual's point of view, …”
Grosser: Early startups should hire nerdy, product-oriented sales reps
“One, you've got to have a product oriented salesperson. So somebody who's going to get deep in your product, geek out on it, can articulate the vision and the product capabilities in line with how a founder would. Which is very different than hiring somebody w…”
Grosser: Tech founders wrongly view salespeople as purely coin-operated
“You know, tech founders have like a real apprehension about sales. There seems to be this point of view that we're all coin operated. We're all effectively like car sales people. Right. And that's just really not actually true.”
Dialpad evaluated sales candidates with half-day office immersions and live chats
“When I was at Dialpad, one of the things we actually did was we brought folks in to the office. It's hard to do it in COVID, but like into the office for like a half day. And we actually just like let them, you know, sit beside our salespeople, stuck them on c…”
Stripe evaluates sales candidates using day-one homework assignments
“That's one of the things we've also done at Stripe, right, is you have a homework assignment, something that's very reflective of what you're going to ask that person to do on day one when they show up. And it's a good way to test whether or not they're going …”
Grosser: Detect candidate exaggeration by probing execution details with how and why
“And so typically, you get at that by increasingly following up Asking why, asking how, and seeing if they can click down into the details, or if they stay at 30,000 feet, very buzzwordy, etc.”
Stripe placed all new hires into customer support queues on day two
“And then, you know, day two, I think we would all get thrown into the support cues. And so that was really great at teaching our users first orientation and getting hands-on experience with customers and learning the product.”
Stripe used team quotas and low leverage before shifting to individual targets
“And then what we did at Stripe was also, we started with team-based quotas. You know, you're learning. We also started with lower leverage. So again, you're not, don't have as much at risk. And as we got better about understanding what was achievable, you know…”
Grosser: New sales reps must focus on product mastery for 90 days
“Number one, first and foremost, is are you mastering the product? And how to talk about it to a customer. So very enablement and learning oriented in the first 90 days.”
Grosser: Top sales reps leverage internal resources rather than executing in isolation
“I always get nervous about sales reps who think they've got it all sorted out, and want to keep you at arm's length, because the best ones typically know where they can leverage other people in the org, and really want to do that.”
Stripe requires leadership gating before pulling product managers into sales calls
“You know, we're thoughtful around having some level of gating so that, you know, whether it's me or another leader is, is deciding when we're pulling product in.”
Grosser: In consumption models, sales are not completed upon contract signing
“So this is like the key challenge, particularly as companies move more and more to consumption based models, the sale is really not done when you sign a contract. Actually at Stripe, we just call it deal signed because that's all it is. We got a piece of paper…”
Grosser: Multi-million dollar enterprise deals require human sales reps
“But when it comes to pursuing larger accounts, multi-million dollar deals, It's pretty rare to do those without a human involved.”
Grosser: Founders must diagnose root causes before replacing underperforming sales heads
“And then the sales team needs to run a diagnostic, you have to get to root cause analysis. I would think that in general, coming out of that, you're going to uncover places in your sales process that are not well tuned that you can fix. And the sales team is a…”
Grosser: Relying solely on inbound marketing slows company growth
“But if you're just sitting there hoping that your marketing org is going to drive you inbound demand, you're probably growing at a slower rate than you could be otherwise.”
Grosser: Reverse-engineer sales goals from win rates and deal sizes
“Sales ultimately is a match And so if you have that target, you can reverse engineer that right of in order to hit this number, you need to close this many deals of this size and take, you know, you win at this rate, it takes this amount of time.”
Grosser: Great sales reps systematically understand the math behind their pipeline
“So a great rep typically would come to me in a one-on-one and say, you know, Jean, my target is X. I'm going to need to close 20 deals to hit that. You know, here are, at this point, the ones that I think are likely to help me get to that number. Here are the …”
Stripe runs mid-cycle deal premortems to proactively address sales risks
“One of the things actually we do is like deal premortems, and we actually call it that, where before you've lost the thing, you know, your mid-cycle, you actually go through a review to think through all the ways in which you could lose this so that you can pr…”
Stripe uses sales loss retrospectives to drive product and GTM strategy
“And then you often find when you've reviewed the losses and you can put in Salesforce loss reasons, those types of things you wind up with like clear go to market challenges where our messaging, our strategies off, as you think about positioning yourself relat…”