The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 25 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Slack Delayed Building an Outbound Sales Motion Too Long During Hypergrowth
“I actually helped to build out our very first ever outbound motion at Slack, was the very first person to ever do it and ever do our first, which we called Proactive outreach. Cause outbound was, you know, of course a dirty word back then, but it is so importa…”
Overly Generous Self-Serve Tiers Cannibalize Future Enterprise Sales Revenue
“Is they have their, essentially their self-serve or their lower end product cannibalize what could be their future enterprise product. We ran into that at Slack. We run into it at Webflow all the time where there has to be a huge product differentiation outsid…”
Startups Should Always Hire Sales Representatives in Cohorts
“You should always hire in multiple sets of sellers, not for competition, but because it's actually not, not that much more work to teach people, you know, teach a group of people than to teach one person.”
Early Slack Sales Reps Received Flat Salaries Without Commissions or Quotas
“As I mentioned, when I came into Slack, there had been absolutely no reach outs ever to anything proactive. Everything that we were doing, our single biggest goal, our single biggest charter was talk to the customers, was understand what is it That the custome…”
Startups Need $1M to $2M ARR Before Building Enterprise Sales Teams
“And once you have conquered those things, again, to recap there, The pain, the product market fit, some revenue, maybe one to two million dollars in ARR, as well as sell outside of the friendlies, that's the time that it is to start building an enterprise prod…”
Asking Sales Candidates to Demo Your Product in Interviews Is a Mistake
“And one of the most common things I think people do quite wrong in their final round is they ask people to demo their product. I think this is one of the absolute worst things that you can do.”
Figma Equity Is Virtually Guaranteed Value Compared to Unknown Startups
“200,000 dollars of equity at Figma is going to be very different than 200,000 dollars at Maybe a small company that doesn't have a good chance of success. And is probably either going to get acquired for a nominal amount or just fizzle out because you know wha…”
Frequent On-Site Travel Is No Longer Necessary in Enterprise Sales
“You no longer need to be on-site Every single time you need to meet with a customer. I used to be on the road at least once a week. I was always on the road. And yes, it's so important for relationship building, but it just, it doesn't need to be that way anym…”
$800B in Lost Wages Occurred as Women Exited the Workforce in 2021
“And a pretty horrifying stat is that last year in 20, 21, there was more women that left the workforce than any other time in the last 35 years. Horrible. There was eight hundred billion dollars in lost wages to women that happened in 20, 21.”
Scaling Startups Should Buy Software for Future Growth, Not Present Size
“Build things for scale. And what I mean by this is don't buy the cheapest tool now because it's meant for an SMB. If you know you're scaling and if you know your hyper growth, build something for, you know, buy and build for next year, for the year after, for …”
Webflow Hosts Websites for 250,000 Daily Active Customers
“For example, at Webflow, we have 250,000 customers every single day hosting their websites on us. It's absolutely massive.”
Founders Must Successfully Sell Their Product Before Hiring Sales Reps
“If you can't be successful as a founder selling your product, how can you ever expect someone else to be successful?”
Slack Did Not Build an SDR Team Until 2017
“At Slack is we didn't even start building an SDR team until 2017. So we had been around for almost three years at that point before we've really ever started dialing up this outbound motion.”
Cold Outbound Emails Should Follow a 10-80-10 Personalization Structure
“We call it the 1080 10. So 10% personalization within this email needs to be about, Hey, Harry, I saw you live, you know, in London. Here's some common things that people like you struggle with. You know, I saw you were over in Finland last weekend, or whateve…”
Webflow Closed Its Record $1M+ Deal via Rapid Self-Serve Follow-Up
“We actually just closed the single largest deal the company has ever had over a million dollar TCV by doing this exact method.”
Early-Stage Founders Should Prioritize Securing Customer Logos Over Revenue
“I advise them to not worry too much about the revenue early days. Focus on getting those logos because very few people ever want to be the very first mover and shaker.”
Discounts Should Primarily Be Used to Control Deal Close Dates
“Discounts should be used Very selectively, and the single biggest reason a discount should be used is to control the close date of the deal.”
Software Buyers Do Not Pay on Monthly Schedules in B2B Deals
“No one pays monthly for any software.”
A Bad Enterprise Sales Hire Can Cost a Startup Up to $1M
“A hiring mistake can cost a company to the tune of one million dollars.”
Hott Mistakenly Authorized a $200,000 Customer Discount as a New Slack Manager
“So I gave the authority to approve a 200,000 dollar credit to a customer at Slack that my team was selling into.”
Stock Option Grants Are Meaningless Without Knowing Total Outstanding Shares
“People get so fixated on the amount of options that they're getting, but options don't actually mean anything. If you don't know how many options are outstanding Or what the actual value is of those options.”
Community Support Is the Most Important Aid Companies Can Provide Working Parents
“And that is the single most important thing that you can do to support parents is, is really give them that, that place where they know where to go. Seek advice and help.”
Taking Over Reps' Deals Is the Biggest Mistake New Sales Leaders Make
“The single biggest mistake I see new sales leaders making Is they go super rep their team's deals, and they run their deals for them, and they just burn themselves out.”