Nov 3, 2023 · 47m · saastr
The Proven Customer Acquisition Strategies Behind Toast's Record Breaking Growth with Toast's CRO
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Toast Chief Revenue Officer Jonathan Vassell breaks down the go-to-market strategies, field sales density models, referral flywheels, and leadership principles that propelled Toast from a Series B startup to a multi-billion dollar public company.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 6.0 Guest teaching 5.8 Guest disagreement 0.2 Jason pushing back 0.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 0:52 Checking host flattery and lowering expectations
Jonathan immediately pushes back on Sam calling him 'legendary', setting expectations lower and insisting success belongs entirely to the team.
Hardest push from Jason ▶ 7:39 Clarifying traditional vs density-based segmentationSam challenges the standard SaaS revenue-tier segmentation model to drill down on Toast's geographic density approach.
Biggest teaching moment ▶ 14:40 Schooling on territory design and the density flywheelJonathan explains the counterintuitive truth that shrinking sales territories actually accelerates rep growth and unlocks local flywheel economics.
Jason holds their own ▶ 10:45 Citing Brex field sales conversion dataSam cites concrete internal metrics from Brex showing on-site sales meetings converted at 45% compared to 15% for remote meetings.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Toast's Platform Offering and the Massive Restaurant Vertical TAM | 4 | 6 | 1 | 0 | Sam opens with high praise and asks Jonathan to break down Toast's market and go-to-market structure. Jonathan politely deflects the 'legendary' label and provides a comprehensive overview of Toast's massive vertical TAM and field-heavy sales motion. | |
| Territory Segmentation Models and Unit Economics of Embedded Payments | 6 | 6 | 0 | 1 | Sam clarifies Toast's unique density-based segmentation model compared to traditional B2B software tiers. Jonathan validates the observation and explains how software plus embedded payments unit economics make distributed field coverage viable. | |
| In-Person Sales Conversion Advantages and the Local Restaurant Ecosystem | 7 | 5 | 0 | 0 | Sam shares conversion benchmark data from Brex showing on-site visits tripled close rates from 15% to 45%. Jonathan builds on this by explaining how in-person presence allows reps to embed into local restaurant supplier ecosystems. | |
| Strategic Territory Design, the Density Flywheel, and Product Influence | 5 | 7 | 1 | 0 | Sam inquires about market rollouts and restaurant segmentation. Jonathan details why smaller territories drive higher rep productivity and describes how product innovations like Toast Go naturally focused reps on full-service dining. | |
| Data Science Application in TAM Scoring and Sales Execution | 7 | 5 | 0 | 0 | Sam demonstrates domain expertise by detailing Brex's deliberate geographic and startup-focused launch strategy in San Francisco. Jonathan connects this to Toast's rigorous data scoring algorithms that prioritize prospect rooftops block by block. | |
| Marketing and Demand Generation for the Non-Desk Restaurant Audience | 5 | 6 | 0 | 0 | Sam asks how marketing targets non-desk restaurant workers compared to desk-bound B2B buyers. Jonathan explains that marketing still fuels the majority of the pipeline alongside local social proof and referral halos. | |
| Scaling Referral Flywheels, Channel Partnerships, and Rapid Experimentation | 7 | 5 | 0 | 0 | Jonathan explains Toast's structured channel partnerships with vendors like US Foods. Sam provides actionable tactical advice on reinforcing referral behavior with handwritten notes, and Jonathan emphasizes continuous testing and iteration. | |
| Scaling Leadership: Advancing from SVP of Sales to CRO in Hypergrowth | 6 | 7 | 0 | 0 | Sam asks how Jonathan successfully avoided being topped as CRO during hypergrowth. Jonathan provides leadership principles centered on scaling operational inputs, maintaining curiosity, and Toast's internal promotion culture. | |
| The Elite High-Performer Mindset: Relentless Drive and Humble Ambition | 7 | 5 | 0 | 0 | Sam outlines his personal philosophy of relentless dissatisfaction and blowing past quota expectations. Jonathan affirms this mentality and defines elite leadership as combining fierce competitiveness with genuine humility. |
Statements from this episode (17)
Blond: Toast had $20M ARR when Jonathan Vassil joined in 2017
“Toast was a series B company with twenty million in ARR”
Vassil: Toast serves up to 85,000 restaurant customers across four countries
“We've got, I think we said today, we've got 80, 85,000 customers across the U.S. And Canada and the U.K. And I, and we're still in our early days, right?”
Vassil: Toast still has 85% of the restaurant market left to capture
“The TAM that we're servicing is one of the largest vertical TAMs in the world with Phil, you know, 85% of the market left to conquer or to tackle, and those opportunities are really, really unique.”
Vassell: Restaurants have higher rooftop density than any other vertical
“There is no other vertical that's, that has that many rooftops. In the U S or across the globe, right? So if you think about any city block, right in San Francisco or Miami or wherever it might be, you may have a pet store, you may have a drug store, right? Yo…”
Vassil: Up to 80% of Toast's sales reps are field-based
“With our sales organization, I, I'd call it, you know, 80, 75 to 80% are field-based sales reps where they are in the market, they own a geography, and they are the trusted advisor to the restaurant space In, in their patch, like, as we like to call it.”
Vassell: Toast inside sales reps have the exact same ARR quotas as field reps
“The quotas are no different, by the way, like that, that inside rep is still going to produce the requisite amount of ARR. As a field rep, they're just going to do it across a different geography.”
Vassell: Distributed field sales requires software plus embedded payments unit economics
“There are other businesses that, or other verticals that don't have the density and that also don't have the unit economics. To get the payback that you need on a distributed workforce, right? We do because of the software plus embedded payments model, right? …”
Blond: In-person sales visits tripled early Brex conversion rates
“One thing that we did in the early days of Brex was we measured conversion rates based off of whether a potential client received an onsite visit or not. And those that a sales rep went on site and met the customer, they closed it like a three X rate. You know…”
Vassil: Smaller sales territories drive higher growth than broad ones
“What we know is the territory size you give the rep will dictate your growth rate, right? And so while we could have given our first rep the entire city of Seattle, We knew that'd be counterproductive going back to the density, right? And so the key is to, and…”
Vassil: High market density directly increases Toast's win rates
“We know definitively, and we've got a ton of data to prove this. When we reach a certain density level within a market our win rates on our top of all actually begin to increase and our reps become more productive.”
Vassil: Toast Had No Sales Reps in California for Years
“We didn't actually have a rep in California for many years after we started, right? Cause it was just better for us to put another rep in Boston”
Blond: Early Brex close rates were significantly higher in SF than NYC
“And by really targeting a specific geo where you talked about this flywheel of customers that can start to engage with other customers the likelihood that we were gonna close a deal when we created an opportunity in San Francisco compared to even New York, whi…”
Vassil: Toast's marketing team drives the majority of its sales funnel
“A majority of our funnel is driven by our marketing team, you know, despite having folks on the ground.”
Vassil: One in five closed Toast deals comes from a referral
“One out of five deals, and we've said this publicly, one out of five deals is referring, right?”
Vassil: Eight in ten happy restaurant customers have referrals to offer
“Ask them if they know of someone that might be in the market, eight times out of 10, they do. Bottom line, eight times out of 10, they do.”