The Ledger
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Alina Vandenberg says European and Outlook-using prospects close significantly slower
“We also observe that we're gonna sell less well if, sorry, they're based in Europe, they take forever to close. If they're on Outlook, for some reason, people that use Outlook, they're a lot slower to make decisions as well and if they're a traditional company…”
Vandenberg: Drift Refuses Small Customers to Mask Churn Problems
“I see the drift is doing that because they've had the churn problem. So then they're trying to make their numbers look better. So they even refuse to take companies.”
Vandenberg: Chili Piper Will Hit $1B Valuation at $20M ARR
“I would say that if we meet our plan by the end of the year, getting the twenty million, we'd be there.”
Vandenberg: Chili Piper Will Hit $100 Per Share, Making Employees Millionaires
“We have a 150 pipers. We promised them all that we're going to get our share price to a hundred dollars a piece so that they're all millionaires every single one of them.”
Chili Piper cuts headcount by one-third, from 250 to 170
“So we cut a third of the company. So we went from two 50 to one 70”
Late-stage investors cannot block sales below Chili Piper's $625M valuation
“They don't have the rights. Those who came into the very high valuation do not have the rights to block.”
Chili Piper achieved cash flow positivity to avoid a down round
“We didn't want to go at a lower valuation, so we said we cut costs, we go cash positive. That's what we do. So that's what we've done.”
Chili Piper raised $33M and sold $33M in secondary to Tiger Global
“We did a secondary with Tiger Global. We sold thirty-three million. So we raised thirty-three million, and we also sold thirty-three million.”
Chili Piper closed a $27M secondary share sale at a $625M valuation
“Yeah, so we did six 25, which was the highest of the market. We, that was in the end, well, at five hundred million with ten million worth of sale, at six 25 with twenty-seven million, so twenty-seven million secondary, and that's what happened.”
Tiger Global Offered Chili Piper a $33M Series B on First Call
“So unsolicited in March, we got an interest from Tiger Global. I got on a call with John Curtis and literally he made the offer on the fly. The later the evening with a term sheet two weeks later with the money for a thirty three million be around.”
Chili Piper's Tiger Round Split $33M Primary and $33M Secondary
“The thirty-three million went into the company. The same amount went into the secondary.”
Vandenberg: Chili Piper sees CAC payback in about one month
“Yeah, that's right. We're getting paid back in about a month, yeah. About a month.”
Chili Piper killed its inbox product over Gmail and Microsoft friction
“We actually had, at some point, an inbox as well, and the inbox was allowing buyers to see their entire buyer's journey and see who at the company emailed, what they did, and so forth. We killed it because we realized that it's going to be so hard to get peopl…”
Alina Vandenberg personally helps unhappy Chili Piper employees find outside jobs
“If I can't find a job in our company that makes them happy, if I don't find the path for them to grow them in my company, I'm going to find them a job outside. And I really go outside of my way to find them a perfect fit.”
Chili Piper doubled ACV and halved CAC over the past year
“Chili Piper's doubled their ACV cut their customer acquisition costs in half, and also dramatically increased revenue per employee, up to 200,000 dollars per employee, all over the course of the last year.”
Chili Piper repriced employee stock options after new 409A valuation
“Yeah, so we repriced the options, so we I went to the board, I said, look I believe the whole idea of stock options is to be motivated which that, so we had another four, nine, eight, it's called to tell us the current correct price, and we repriced all our op…”
Chili Piper plans Q1 AI scheduler as 'ChatGPT for Calendly'
“We have something coming in the first quarter that we think is the chat GPT of Calendly, you know, but we'll see.”
Vandenberghe: Chili Piper growth is driven by virality over SEO
“So it's more the viral aspect than the SEO that's working for us. SEO, to be a candidate, I think we can do better, and we get back to it next year.”
Chili Piper employee satisfaction dropped from 92% to 75% following layoffs
“We were at 92% before Morocco. We redid it in January, we were at 75%.”
Chili Piper burned $2M per month before enacting layoffs
“We were burning, it went to two million a month.”
Chili Piper faced revenue contraction and a 50% drop in new logos
“Instead of organic expansion, we had contraction. Instead of new logos, we had half of new logos.”
Chili Piper transitioned to cash flow positive in just four months
“Yeah, so so November, December, January, February.”
Chili Piper ties account manager bonuses entirely to cross-selling over NDR
“So we switch our AM bonus entirely on cross-selling. They're no longer compensated on NDR. They're only compensated on cross-selling.”
Vandenberghe says 42 VCs reached out to lead Chili Piper's Series C
“I had 42, that's the number, VCs who had reached out to me to say, we want to do your C-Round, we want to do your C-Round”
Chili Piper enforces a strict no-discount policy across enterprise sales
“By the way, we have a no discount policy. So I do about five rounds of negotiation with, not negotiation with the procurement Facebook.”
Tiger Global pushed Chili Piper to adopt Oyster for global contractor compliance
“But then when we did our B run the attorney for Tiger Global said that doesn't look very safe, like from a liability standpoint, right? And so we said, okay, we'll move to Oyster.”
Structure customer-funded software dev as prepayments to retain intellectual property
“You can't do a service. The fee has to be a prepayment against software because otherwise they own the IP, right? If you do a service business, you do develop for them and they own the IP. So the, it's very important if you ever do something like that, where y…”
Two Ukrainian engineers made $1.6M each for one month of work
“We gave them shares. A 100,000 shares each. And as I said, the secondary is 16 dollars a share. So each of them, that pair for the months was 1.6 million each.”
Vandenberghe: Base10 offered Chili Piper $15M on $55M pre at 12x ARR
“So that deal was June 20, 20. It was based then. And they offered 15 on 55 pre.
28 years.
So we're doing around four plus million.
So it's, it was
around 12 X. There was a number, 12 X run rate.”
Latka: Chili Piper Sold $7M Secondary at a $625M Valuation
“We're seeing, you know, Chili Piper just sold seven million secondary at a six hundred twenty five million valuation with fifteen million in revenue, but that's very different than what Lemless just did, which was sell thirty million for 20% of business at one…”
Vandenberg: Event Badge Scanning Fails to Build Pipeline Compared to Meetings
“So scan badges is nice but that doesn't get you pipeline. Yeah. Then you have to follow up for email them, go through the same thing. So all of them realize that what matters is try to get meetings ahead of time and meetings on the floor instead of go straight…”
Vandenberg: All Chili Piper Customers Double Inbound Conversion Rates
“And what happened is that all our customers double the inbound conversion rate. So they go from 40 to 80% or from 20, some went from 23% to 75%, right?”
Vandenberg: Chili Piper Will Not Sell to ZoomInfo or Gong
“That is not in our future. No, Alina
and I have built this company. We having a blast.”
Vandenberg: Hardest Part of Inbound Is Real-Time Qualification and Routing
“But the hard part is not to show a calendar. The hard part is to do the real-time qualification and routing.”
Vandenberg: Early Chili Piper investors saw 50x to 100x secondary returns
“Some of them You know, came in very early and they did a 50 or a hundred X. Yeah.”
Vandenberg: Chili Piper enforces a strict no-discount pricing policy
“One thing remarkable about TV Piper is that we have a no discount policy. So nobody, we just don't know discounts. And even these companies that I mentioned, there are very large companies with procurement department bigger than our company pay the same price.”
Vandenberg: $40M pre-money valuation is fair for Chili Piper
“Yeah, I think that's fair for us now. The market will tell me.”
Alina Vandenberg says Chili Piper is cash break-even and growing
“There are a lot of things that have happened this year, but we're cash break even, and we're continuing to grow.”
Alina Vandenberg says Chili Piper books 500 meetings quarterly using AI
“That's how we managed to book 500 meetings a quarter”
Chili Piper achieves positive cash flow without raising new capital
“No, we switched to being cash positive.”
Chili Piper launched and quickly pulled 'Inbox' email client in 2020
“So little known is the fact that in 2020 we launched a product called inbox. Because we thought, okay, we need to help people engage with their buyer, and there is a lot of things happening in the inbox, so let's do an inbox, an email inbox, which came out lik…”