The Science of Scaling · 2 Apr 2025
Create a Billion Dollar Sales Culture w/ Greg Holmes (CRO, Zoom)
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Greg Holmes, Zoom's first sales hire and later its CRO, describes joining in January 2013 before the company had revenue and building the sales team that helped it find go-to-market fit. He covers how he learned from free users and early customers, the free-tier upgrade trigger, how he hired and assessed reps, how he kept a culture of delivering happiness, and how sales worked with engineering. Host Mark Roberge adds commentary on how these moves relate to go-to-market fit and culture at scale. The main argument is that early sales leaders should learn directly from users and customers before pushing for paid commitments.
For founders
- Greg says the first sales hire should start by calling existing free users and top customers to learn why they chose the product, before pitching anything.
- Greg says Zoom's free plan with a 40-minute limit was the upgrade trigger, and it worked well enough that Zoom did not hire a head of marketing until around 2014 or 2015.
- Greg says Zoom's first team was 13 engineers in China with a single seller, and a rep who relayed customer needs to engineering helped produce the room connector in about three months.
- Mark says a published culture deck can describe the culture a company aspires to, which attracts people who want that culture and helps new hires reinforce it.
For revenue leaders
- Greg says a new head of sales should call top customers in each segment within the first couple of weeks.
- Greg says customers who just bought online need onboarding help and information gathering, not sales follow-up.
- Greg says he sat in on every salesperson interview and asked candidates for examples of when they delivered happiness.
- Mark says a sales candidate can be tested by having them use the product for two days and then present feedback to the engineering team.
What was said 20, most useful first
A new head of sales should call the company's top customers in each segment within the first few weeks. Listen
Greg says he advised a company that had just hired a new head of sales to call its top customers in each segment in the first couple of weeks, and that the new hire had not yet done this. He describes it as one of the first things a new sales leader should do.
“I'm like, you called your top customers. and each segment and start figuring out and he hadn't done that yet.”
Listen to the episode Sales process & deals Link to this Report a problem
Early on, a first seller can study free users from the same corporate domains and call them to learn why they chose the product over alternatives. Listen
When Greg joined Zoom in January 2013 most users were free, and the only sign-up options were Facebook and Google sign-in. He pulled free-user data, filtered for users from the same corporate domains, and called those companies to ask what made them start using Zoom instead of WebEx, finding people who were enthusiastic about it.
“I started digging into that data I started looking at you know free users of similar you know same corporate domains and I started calling into You know those companies”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Customers who buy online need a different approach from inbound leads: send an onboarding email with best practices, help them, and gather information. Listen
When Zoom turned on its website and online purchasing in late January, single Pro license buyers started arriving. Greg's team sent a thank-you email with best practices and links, treating these buyers as customers who were already done buying rather than new leads. Greg says that by helping them and gathering information you may find, for example, that a buyer is at a 100-person company with ten more people like them, and ask why the other nine aren't on Zoom.
“These people just bought something. They're kind of done. Just get in there and help them and then gather, get some information.”
Listen to the episode Retention & customer success Link to this Report a problem
A 40-minute limit on the free plan was the upgrade trigger, and Zoom kept that model long after launch. Listen
Greg says the team trusted that the 40-minute limit would push users in critical business meetings to upgrade, and that PLG worked so well as the company's marketing that Zoom did not hire a head of marketing until 2015, or maybe late 2014. Mark adds that the free tier ended at 40 minutes and that Zoom still kept this strategy during COVID years later.
“it was like ultimately that 40 minute time limit if they're in a critical business meeting they're not going to want it to time out though they'll move over”
Listen to the episode Pricing & packaging Link to this Report a problem
A candidate can be tested by having them use the product for two days and then present feedback to the engineering team in a later interview. Listen
Mark says he gives new sales hires at this stage a two-day product exercise, then has them deliver feedback to engineering as part of the next interview. He says the point is to see whether a candidate can look at the product holistically and communicate with engineering in a way that speaks their language.
“spend the next two days going through our product, go use it, come up with feedback and deliver it to”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
Greg hired sellers for their ability to listen and care, not only for their quota results. Listen
Greg says Zoom's CEO Eric Yuan made delivering happiness the company's mission from the start, and it became the company's culture. When hiring, Greg looked for sellers who are good people who listen and care, and he admits that these people are harder to find because some nice people do not always finish first.
“They're not the nicest person, you know, they just go grind out deals”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
A rep relaying customer needs to engineering quickly led to a room connector that Zoom built in about three months and used to win against BlueJeans. Listen
Daniel, one of the first two reps Greg hired, went from his calls straight to the engineering office with what he was hearing, and pushed for the product to connect video endpoints with browsers and Skype. Greg says the engineering team built the first version, called the room connector, within about three months, and the company started winning against BlueJeans, which had been connecting endpoints.
“Within like three months we had like first version of this we called it the room connector and all of a sudden we started knocking out knocking out BlueJeans”
Before taking a customer request to product and engineering, ask whether it will help one customer or many. Listen
Greg says the team trained reps to ask whether a requested feature would help only one customer or a broad set of customers. They also asked whether a large customer could become a website name or case study, and only escalated when they felt they had something with real impact.
“Is this just going to help this one customer or is this something that's going to help this customer?”
Outreach to existing free users should open with genuine curiosity about how they found the product, not with a pitch. Listen
Greg says his calls to free users were driven by sincere curiosity about how they found Zoom and why they chose it over other options. He says a genuinely curious tone gets people to respond, and he advises founders and early sellers to use the same approach.
“It was genuine, you know, curiosity. I really wanted to really wanted to understand how they found Zoom.”
Listen to the episode Pipeline & demand generation Link to this Report a problem
Continuing to sales-call people who already use the free product makes them ask why they are being contacted. Listen
Greg says his first reps initially went after existing free users, but this did not work. Users who were already happy with the product asked why the company kept calling them, so the team had to change its approach.
“If you're kind of continuing to hammer people that are already using your product, they're kind of like, why do they keep calling me?”
Listen to the episode Sales process & deals Link to this Report a problem
Zoom's first team was 13 engineers in China, one support person, a product and marketing lead, a few engineering leads, and one seller, with no head of marketing yet. Listen
Greg describes the early team when he joined in January 2013. The engineers were based in China, and the team included an architect who did front-end and back-end work, with Greg as the only seller and no marketing hire yet.
“So we had 13 engineers in China and then it was Eric our head of product Nick Chong he was kind of he was sort of doing product and marketing we had one support guy”
Listen to the episode Hiring & team building Link to this Report a problem
Early reps should talk with engineers about what they hear from customers, and the sales floor should celebrate with engineering. Listen
Greg says his reps regularly talked to engineers about what they were hearing and seeing about the product. The team invited engineers to happy hours and celebrated quarters on the sales floor, so engineers felt part of the company's results as sales joined.
“the reps were always good going and talking to the engineers about what they're hearing or seeing about the product”
Listen to the episode Leadership & culture Link to this Report a problem
Interview candidates by asking for a concrete example of when they delivered happiness, both at work and in their personal life. Listen
Greg asked salespeople for examples of times they had delivered happiness in their outside life and at work, and when they had last done so. He says candidates had rarely heard the question, and that it told him a lot despite being simple.
“give me some examples where you've delivered happiness in your life, maybe in your just your outside life, and maybe at work, when's the last time you delivered happiness, give me an example.”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
Weekly all-hands can keep a culture visible by showcasing examples of the behaviour the company wants. Listen
At Zoom's weekly all-hands, slide boards showed people who had delivered happiness that week, whether to a colleague or a customer, and Greg did the same in sales meetings. He asked reps to forward any customer email, chat or voicemail confirming happiness, and later Eric created a Chief Happiness Officer role.
“we would put up you know, examples on slide boards of people that delivered happiness in that past week”
Listen to the episode Leadership & culture Link to this Report a problem
Greg met every salesperson before they accepted an offer, so he could know them and set up a connection before they joined. Listen
Greg says he wanted to be part of every interview for any salesperson Zoom hired, so he could meet them and make sure they would be a good part of the team. He recommends doing this before the candidate accepts, so the new hire already has a connection when they join.
“I wanted to be in every interview for any salesperson that we hired. I wanted to, I wanted to meet them and know them”
Listen to the episode Sales team, hiring & comp Link to this Report a problem
A published culture deck can describe the culture a company aspires to, which attracts people who want it and helps new hires reinforce it. Listen
Mark says HubSpot was inspired by Netflix's culture deck, and that he thinks Amazon did something similar. He says the deck does not have to match current culture exactly, since it describes what the company aims to be, and that this makes culture scalable.
“Sometimes it's not an exact description of your current culture, but it's what you aspire to be.”
Listen to the episode Leadership & culture Link to this Report a problem
Culture is set by behaviour at 10 to 40 people, but at thousands of reps across continents leaders must reinforce it through what they highlight in meetings. Listen
Mark says in the early days a small team's behaviour dictates its culture. He says this becomes harder at a scale such as 2,000 reps across three or four continents, and that leaders reinforce culture through what they highlight in a one-hour team meeting, such as a big deal or an example of creating happiness.
“It becomes harder when your team is 2,000 reps and they're across three or four continents.”
Listen to the episode Leadership & culture Link to this Report a problem
Go-to-market fit in this phase means reps learning why customers use the product and what goals they have, not pitching a package. Listen
Mark describes Zoom as moving from product-market fit, which he ties to customers realising value from the product (in Zoom's case daily active usage), to finding go-to-market fit. He notes Greg was not hypothesising a pro package to pitch, but learning why customers used the product and what they were trying to accomplish, which he compares to customer success work.
“He's going out there to understand why customers are using the product. Learning. Understanding the goals that they're trying to accomplish.”
Listen to the episode Strategy & market Link to this Report a problem
When choosing a job, weight the category more than the company. Listen
Mark advises that if you pick the right category but the wrong company, you will probably get scooped up by the winner in the long run, which will be great for your career. If you pick the right company in a category with heavy headwinds, you will face headwinds in your career too. He used Greg's conviction about online collaboration as an example.
“put more weight on the category not the company”
Greg got an early growth opportunity by pitching Canada as its own business unit at Webex. Listen
Greg says he pitched breaking Canada out of the US-Canada line in Webex's slide decks, and his president let him run with it. He says he ended up building a sizeable business focused on the Canadian business unit, which he believes was a big reason he was noticed.
“I pitched Canada actually at WebEx. Why is it always US-Canada on the slide deck?”
Listen to the episode Strategy & market Link to this Report a problem