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Sep 14, 2021 · 24m · top-founders

ChiliPiper Meeting Tool Hits $12m Run Rate, Approaching Unicorn Status

Nicolas Vandenberghe · 15m spoken Nathan Latka · 5m spoken
0:00 / 0:00

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In this interview with Nathan Latka, Chili Piper co-founder and CEO Nicholas Vandenberg details how the company grew past $10M ARR toward a $20M run rate, highlighting their $66M Tiger Global funding deal, inbound lead routing technology, and long-term vision of turning all 150+ employees into equity millionaires.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 27.6% of the talking time here. How this is scored →

Nathan as informed peer 6.0 Guest teaching 4.3 Guest disagreement 2.4 Nathan pushing back 4.1
05100:0010:0020:000:44–3:54 · Nathan as informed peer 5/10 Overcoming Pandemic Disruptions and Driving Rapid Revenue Expansion Nathan prompts Nicholas on how Chili Piper grew so quickly after COVID. Nicholas walks through applying for PPP, surging demand for inbound conversion, raising a Series A, and landing a Series B from Tiger Global.3:54–7:22 · Nathan as informed peer 4/10 Co-Founding Dynamics and the 50-50 Spousal Partnership Nathan frames Chili Piper as primarily a scheduling utility. Nicholas politely rejects this premise and educates Nathan on the complex backend marketing automation, real-time qualification, and routing logic that actually drives their value.7:23–10:34 · Nathan as informed peer 8/10 Strategic Fundraising, Tiger Global Deal Mechanics, and Secondary Liquidity When Nicholas declines to give the exact valuation of the Tiger Global round, Nathan leverages his knowledge of Tiger's typical ownership targets and deduces the existence of a matching $33M secondary transaction.10:35–13:37 · Nathan as informed peer 8/10 Path to Unicorn Valuation, High NRR, and Customer Cohorts Nathan demonstrates high domain fluency by detailing Gong's ARR and valuation multiples, while Nicholas explains Chili Piper's NRR breakdown across SMB, mid-market, and enterprise tiers.13:38–16:38 · Nathan as informed peer 5/10 Customer Milestones, Enterprise Contracts, and Pricing Strategy Nathan inquires about customer counts, contract sizing, and the rationale behind expanding into Chili Events. Nicholas details their $750k largest ACV and how event managers need immediate meeting bookings instead of badge scanning.16:39–19:27 · Nathan as informed peer 6/10 Organizational Scaling, Team Allocation, and Nuanced Sales Quotas Nathan asks about standard SaaS sales quotas and compensation models. Nicholas explains why Chili Piper eschews fixed quotas in favor of dynamic quotas tailored to rep seniority and inbound pipeline allocation.19:28–23:54 · Nathan as informed peer 6/10 Inbound M&A Strategy and Long-Term Employee Wealth Creation Nathan catches Nicholas off guard with a rumor about buying a company, then playfully goads him into confirming the company's valuation is well above $100M while Nicholas shares his goal of making every employee a millionaire.0:44–3:54 · Guest teaching 2/10 Overcoming Pandemic Disruptions and Driving Rapid Revenue Expansion Nathan prompts Nicholas on how Chili Piper grew so quickly after COVID. Nicholas walks through applying for PPP, surging demand for inbound conversion, raising a Series A, and landing a Series B from Tiger Global.3:54–7:22 · Guest teaching 8/10 Co-Founding Dynamics and the 50-50 Spousal Partnership Nathan frames Chili Piper as primarily a scheduling utility. Nicholas politely rejects this premise and educates Nathan on the complex backend marketing automation, real-time qualification, and routing logic that actually drives their value.7:23–10:34 · Guest teaching 3/10 Strategic Fundraising, Tiger Global Deal Mechanics, and Secondary Liquidity When Nicholas declines to give the exact valuation of the Tiger Global round, Nathan leverages his knowledge of Tiger's typical ownership targets and deduces the existence of a matching $33M secondary transaction.10:35–13:37 · Guest teaching 4/10 Path to Unicorn Valuation, High NRR, and Customer Cohorts Nathan demonstrates high domain fluency by detailing Gong's ARR and valuation multiples, while Nicholas explains Chili Piper's NRR breakdown across SMB, mid-market, and enterprise tiers.13:38–16:38 · Guest teaching 5/10 Customer Milestones, Enterprise Contracts, and Pricing Strategy Nathan inquires about customer counts, contract sizing, and the rationale behind expanding into Chili Events. Nicholas details their $750k largest ACV and how event managers need immediate meeting bookings instead of badge scanning.16:39–19:27 · Guest teaching 6/10 Organizational Scaling, Team Allocation, and Nuanced Sales Quotas Nathan asks about standard SaaS sales quotas and compensation models. Nicholas explains why Chili Piper eschews fixed quotas in favor of dynamic quotas tailored to rep seniority and inbound pipeline allocation.19:28–23:54 · Guest teaching 2/10 Inbound M&A Strategy and Long-Term Employee Wealth Creation Nathan catches Nicholas off guard with a rumor about buying a company, then playfully goads him into confirming the company's valuation is well above $100M while Nicholas shares his goal of making every employee a millionaire.0:44–3:54 · Guest disagreement 1/10 Overcoming Pandemic Disruptions and Driving Rapid Revenue Expansion Nathan prompts Nicholas on how Chili Piper grew so quickly after COVID. Nicholas walks through applying for PPP, surging demand for inbound conversion, raising a Series A, and landing a Series B from Tiger Global.3:54–7:22 · Guest disagreement 4/10 Co-Founding Dynamics and the 50-50 Spousal Partnership Nathan frames Chili Piper as primarily a scheduling utility. Nicholas politely rejects this premise and educates Nathan on the complex backend marketing automation, real-time qualification, and routing logic that actually drives their value.7:23–10:34 · Guest disagreement 3/10 Strategic Fundraising, Tiger Global Deal Mechanics, and Secondary Liquidity When Nicholas declines to give the exact valuation of the Tiger Global round, Nathan leverages his knowledge of Tiger's typical ownership targets and deduces the existence of a matching $33M secondary transaction.10:35–13:37 · Guest disagreement 2/10 Path to Unicorn Valuation, High NRR, and Customer Cohorts Nathan demonstrates high domain fluency by detailing Gong's ARR and valuation multiples, while Nicholas explains Chili Piper's NRR breakdown across SMB, mid-market, and enterprise tiers.13:38–16:38 · Guest disagreement 1/10 Customer Milestones, Enterprise Contracts, and Pricing Strategy Nathan inquires about customer counts, contract sizing, and the rationale behind expanding into Chili Events. Nicholas details their $750k largest ACV and how event managers need immediate meeting bookings instead of badge scanning.16:39–19:27 · Guest disagreement 3/10 Organizational Scaling, Team Allocation, and Nuanced Sales Quotas Nathan asks about standard SaaS sales quotas and compensation models. Nicholas explains why Chili Piper eschews fixed quotas in favor of dynamic quotas tailored to rep seniority and inbound pipeline allocation.19:28–23:54 · Guest disagreement 3/10 Inbound M&A Strategy and Long-Term Employee Wealth Creation Nathan catches Nicholas off guard with a rumor about buying a company, then playfully goads him into confirming the company's valuation is well above $100M while Nicholas shares his goal of making every employee a millionaire.0:44–3:54 · Nathan pushing back 3/10 Overcoming Pandemic Disruptions and Driving Rapid Revenue Expansion Nathan prompts Nicholas on how Chili Piper grew so quickly after COVID. Nicholas walks through applying for PPP, surging demand for inbound conversion, raising a Series A, and landing a Series B from Tiger Global.3:54–7:22 · Nathan pushing back 2/10 Co-Founding Dynamics and the 50-50 Spousal Partnership Nathan frames Chili Piper as primarily a scheduling utility. Nicholas politely rejects this premise and educates Nathan on the complex backend marketing automation, real-time qualification, and routing logic that actually drives their value.7:23–10:34 · Nathan pushing back 8/10 Strategic Fundraising, Tiger Global Deal Mechanics, and Secondary Liquidity When Nicholas declines to give the exact valuation of the Tiger Global round, Nathan leverages his knowledge of Tiger's typical ownership targets and deduces the existence of a matching $33M secondary transaction.10:35–13:37 · Nathan pushing back 4/10 Path to Unicorn Valuation, High NRR, and Customer Cohorts Nathan demonstrates high domain fluency by detailing Gong's ARR and valuation multiples, while Nicholas explains Chili Piper's NRR breakdown across SMB, mid-market, and enterprise tiers.13:38–16:38 · Nathan pushing back 2/10 Customer Milestones, Enterprise Contracts, and Pricing Strategy Nathan inquires about customer counts, contract sizing, and the rationale behind expanding into Chili Events. Nicholas details their $750k largest ACV and how event managers need immediate meeting bookings instead of badge scanning.16:39–19:27 · Nathan pushing back 4/10 Organizational Scaling, Team Allocation, and Nuanced Sales Quotas Nathan asks about standard SaaS sales quotas and compensation models. Nicholas explains why Chili Piper eschews fixed quotas in favor of dynamic quotas tailored to rep seniority and inbound pipeline allocation.19:28–23:54 · Nathan pushing back 6/10 Inbound M&A Strategy and Long-Term Employee Wealth Creation Nathan catches Nicholas off guard with a rumor about buying a company, then playfully goads him into confirming the company's valuation is well above $100M while Nicholas shares his goal of making every employee a millionaire.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 34.1% · guest 65.9%0:00 · Nathan 34.1% · guest 65.9%3:00 · Nathan 20.8% · guest 79.2%3:00 · Nathan 20.8% · guest 79.2%6:00 · Nathan 20.2% · guest 79.8%6:00 · Nathan 20.2% · guest 79.8%9:00 · Nathan 42.8% · guest 57.2%9:00 · Nathan 42.8% · guest 57.2%12:00 · Nathan 21.3% · guest 78.7%12:00 · Nathan 21.3% · guest 78.7%15:00 · Nathan 15.3% · guest 84.7%15:00 · Nathan 15.3% · guest 84.7%18:00 · Nathan 18% · guest 82%18:00 · Nathan 18% · guest 82%21:00 · Nathan 33.6% · guest 66.4%21:00 · Nathan 33.6% · guest 66.4%24:00 · Nathan 99% · guest 1%24:00 · Nathan 99% · guest 1%
Sharpest disagreement ▶ 4:33 Rejecting the simple scheduling tool framing

Nicholas firmly reframes Nathan's assumption that Chili Piper is just a calendar tool, highlighting the misconception and explaining their core real-time routing moat.

 Hardest push from Nathan ▶ 9:18 Pushing for secondary liquidity details

Nathan refuses to accept the vague round description and directly deduces that the unsolicited Tiger round included substantial secondary shares.

 Biggest teaching moment ▶ 5:05 Explaining inbound lead conversion math

Nicholas details the mathematical breakdown of why 40% inbound conversion is a failure and how bridging marketing automation forms with Salesforce solves it.

 Nathan holds their own ▶ 11:28 Nathan breaks down SaaS unicorn multiples

Nathan demonstrates sharp industry expertise by quoting Gong's ARR, total capital raised, and multiple to illustrate why growth rate and NRR command market premiums.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Overcoming Pandemic Disruptions and Driving Rapid Revenue Expansion 5213 Nathan prompts Nicholas on how Chili Piper grew so quickly after COVID. Nicholas walks through applying for PPP, surging demand for inbound conversion, raising a Series A, and landing a Series B from Tiger Global.
Co-Founding Dynamics and the 50-50 Spousal Partnership 4842 Nathan frames Chili Piper as primarily a scheduling utility. Nicholas politely rejects this premise and educates Nathan on the complex backend marketing automation, real-time qualification, and routing logic that actually drives their value.
Strategic Fundraising, Tiger Global Deal Mechanics, and Secondary Liquidity 8338 When Nicholas declines to give the exact valuation of the Tiger Global round, Nathan leverages his knowledge of Tiger's typical ownership targets and deduces the existence of a matching $33M secondary transaction.
Path to Unicorn Valuation, High NRR, and Customer Cohorts 8424 Nathan demonstrates high domain fluency by detailing Gong's ARR and valuation multiples, while Nicholas explains Chili Piper's NRR breakdown across SMB, mid-market, and enterprise tiers.
Customer Milestones, Enterprise Contracts, and Pricing Strategy 5512 Nathan inquires about customer counts, contract sizing, and the rationale behind expanding into Chili Events. Nicholas details their $750k largest ACV and how event managers need immediate meeting bookings instead of badge scanning.
Organizational Scaling, Team Allocation, and Nuanced Sales Quotas 6634 Nathan asks about standard SaaS sales quotas and compensation models. Nicholas explains why Chili Piper eschews fixed quotas in favor of dynamic quotas tailored to rep seniority and inbound pipeline allocation.
Inbound M&A Strategy and Long-Term Employee Wealth Creation 6236 Nathan catches Nicholas off guard with a rumor about buying a company, then playfully goads him into confirming the company's valuation is well above $100M while Nicholas shares his goal of making every employee a millionaire.

Statements from this episode (16)

Assertion Not checkable as stated
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 2:58
Assertion Not checkable as stated
Chili Piper Crosses 150 Employees and $10M Run Rate
“We passed 150 employees. We actually passed the ten million mark earlier this year, so we're not, not aiming for the twenty million mark.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 3:26
Prediction Not checkable as stated
Vandenberg: Chili Piper Plans to Hit $20M ARR by End of 2021
“Well, that's the plan, yeah.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 3:51
Assertion Not checkable as stated
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?”
Nicolas Vandenberghe Sep 14, 2021 ▶ 6:13
Insight
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 6:26
Disclosure
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 9:49
Assertion Not checkable as stated
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 10:10
Prediction Not checkable as stated
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 10:45
Opinion
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 12:54
Assertion Not checkable as stated
Vandenberg: Chili Piper Enterprise Net Revenue Retention Exceeds 150%
“Our trend is super high in this SMB, and our net revenue retention is a hundred percent, but our net revenue retention in the enterprise space is north of a 150%, like the number you mentioned, and the market is in between.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 13:07
Disclosure
Vandenberg: Chili Piper has surpassed 1,000 total customers
“So we passed a thousand.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 13:44
Disclosure
Vandenberg: Chili Piper's largest enterprise contract is $750,000 ACV
“It's three quarter of a million and I can't name the customer.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 13:58
Insight
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…”
Nicolas Vandenberghe Sep 14, 2021 ▶ 14:55
Disclosure
Vandenberg: Chili Piper Employs 20 SDRs, 20 AEs, and 15 AMs
“We're about 20, 20, 15. So 20 SDRs, 20 AEs, 15 AMs.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 17:09
Disclosure
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 20:51
Prediction Not checkable as stated
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.”
Nicolas Vandenberghe Sep 14, 2021 ▶ 20:56
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