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Actionable
Takeaways
Pause mid-execution when customer feedback reveals flawed rollout assumptions:
Zocdoc tested their new pricing model successfully in lower-penetration states, then moved to New York where they represented a much larger percentage of doctor practices. Oliver recalls: "I literally had a conversation with one of our early clients that said, 'Oliver, I understand what you're doing, and I understand that this is a great outcome, but you have to give me more time to adjust because it has completely different cash flow implications for me as a business.' That's when the penny dropped." Despite having just created a burning platform with employees that "we do this or we're dead," he stopped the rollout entirely and implemented a gradual transition path. The tactical insight: test pricing changes in representative segments that match your core market's dependency level, not just in any available market.
Negative churn validates pricing power even through brutal transitions:
More than half of Zocdoc's doctors paid less under the new model and welcomed it, but those paying 10-100x more often left initially—then returned. Oliver explains: "Nearly all of them came back because as they had time to cool off and reflect on the situation and see the impact that we've had on their business and that we could continue to have on their business, they realized this is really a good deal and maybe what they had before was just too good to last." For marketplace businesses reconsidering pricing, this suggests tolerance for temporary churn when value delivery is defensible. The insight: if your highest-volume users return after cooling off, your pricing correction was overdue, not overreaching.
Intentionally choose friction that becomes a moat:
Zocdoc deliberately avoided cosmetic surgery and other specialties eager for patient acquisition, targeting instead primary care doctors and specialists who were hardest to convince. Oliver spent 3-4 hours until 10-11pm convincing their first primary care doctor to join. "We looked at this and said, okay, this is the friction. But that also means this will turn into a fantastic mode once we get to scale and build our brand. And it was just like that." For two-sided marketplaces, solving for the most skeptical, valuable supply creates defensibility that easy wins cannot. The key decision: will competitors replicate your easy supply or struggle with your hard-won supply?
Organic discovery scales when you compress time-to-value from 31 days to same-day:
Over 60% of Zocdoc's bookings are repeat users or word-of-mouth, requiring limited marketing spend 18 years in. Oliver attributes this to the contrast: "If you pick up the phone and dial for doctors, it takes on average 31 days to get an appointment with a primary care doctor. On Zocdoc, you can do that same day." This 31x compression in time-to-value created "social currency in telling your friends." For product-led growth, the insight isn't just solving a problem—it's creating a before-and-after experience so stark that silence feels like withholding valuable information from your network.
Marketplace complexity scales exponentially by dimension:
Oliver describes healthcare not as managing one market but "hundreds of markets, literally neighborhood by neighborhood, specialty by specialty, insurance by insurance. It multiplies out very quickly. Nationwide we're managing tens of millions of sub-markets and need to make sure we have supply and demand in harmony." This level of complexity required physical war-room planning: "We had a huge map of New York on the wall physically with pins that designated where doctors of certain specialties are and what kind of insurances they took." For founders building marketplaces with multiple constraint dimensions, this suggests early investment in tooling for visibility across segment combinations, not just aggregate metrics.
Conversation
Highlights
How Zocdoc Survived Raising Prices 100x and Nearly Dying at Year 10
Oliver Kharraz spent 3-4 hours until 11pm convincing Zocdoc‘s first primary care doctor to join the platform. The physician was skeptical—worried about “crazy people booking on the Internet,” as Oliver recalls. But that friction signaled something valuable.
Today, one in three new doctor-patient relationships in New York City are formed through Zocdoc. Over 60% of bookings come from repeat users or word-of-mouth. But reaching this scale required surviving what Oliver describes as the company’s darkest moment: a business model transition that raised prices up to 100x for some customers and halted new customer acquisition for years.
In a recent episode of Unicorn Builders, Oliver shared the brutal mechanics of that turnaround and the tactical decisions that determined whether Zocdoc would survive.
The Economics That Nearly Killed Them
Ten years into building Zocdoc, Oliver faced a fatal mismatch between value delivery and revenue capture. “We were in a situation where we were barely growing 1%. And we were losing money on a unit basis. So we traded dollars for quarters and we had barely any runway left, so we were going to run out of money within the year.”
The core issue: flat subscription pricing regardless of utilization. “We charged every doctor on Zocdoc the same amount of money in a subscription, even though some doctors got thousands of patients from us a year and some maybe just a handful,” Oliver explains. This pricing model subsidized low-value customers with high-value ones—a formula for negative unit economics at scale.
The required pivot to pay-per-booking meant: federal and state law changes to enable the new billing structure, complete infrastructure rebuilds for charging and service delivery, hiring leaders with skill sets irrelevant under subscriptions, and converting every existing customer to the new model. Most critically: “Because our salesforce is engaged with selling customers we already have, there will be no growth, presumably for several years.”
Some leadership self-selected out when Oliver presented this plan. “I think that is completely fair and probably risk adjusted, maybe the right decision,” he notes. But most stayed, motivated by the mission of giving patients healthcare access.
Managing Thousands of 100x Price Increase Conversations
The transition required repricing every customer based on actual utilization. For high-volume practices, the increases were extreme. “The conversation we had to have with a lot of our providers is that, oh, your price goes up by 10x or 20x or in some extreme cases 100x,” Oliver recalls.
“They are sometimes emotional, there’s some choice words being used. Sometimes the volume goes up. And we had to have thousands and thousands of these types of conversations.”
The immediate churn was significant: “A lot of the providers that we had these types of conversations with stopped using Zocdoc during that phase.”
But the retention pattern that followed validated the pricing correction: “Nearly all of them came back because as they had time to cool off and reflect on the situation and see the impact that we’ve had on their business and that we could continue to have on their business, they realized that this is really a good deal and maybe what they had before was just too good to last.”
For marketplace founders reconsidering pricing, this suggests tolerance for temporary churn when value delivery is defensible. If your highest-volume users return after reflection, your pricing was overdue for correction.
When to Stop a Rollout Mid-Execution
After successful pilots in lower-penetration states, Oliver greenlit the New York rollout—Zocdoc’s highest-dependency market where they powered significant portions of practice revenue.
A conversation with an early client revealed his testing methodology was flawed: “He said, ‘Oliver, I understand what you’re doing, and I understand that this is a great outcome, but you have to give me more time to adjust to that because it has completely different cash flow implications for me as a business.’ And that’s really when the penny dropped for me.”
Doctors in test markets viewed Zocdoc as incremental acquisition. Doctors in New York relied on Zocdoc for baseline patient flow. The cash flow impact of sudden 10-100x increases was fundamentally different.
Oliver made a decision that contradicted his recent all-hands: “I stopped the train. I said, we are pausing the rollout in New York and we’ll find a pathway that’s much more gradual, that gives our clients a lot more time to get ready for that.”
The leadership challenge was significant: “I just weeks before stood in front of the entire company and created this burning platform of we have to do this or we are dead. And now I said, okay, I was essentially just kidding.”
The tactical lesson: test pricing changes in segments that match your core market’s dependency characteristics. Success in low-dependency segments doesn’t predict outcomes in high-dependency ones.
Choosing Friction as Competitive Advantage
Zocdoc’s early supply-side strategy deliberately targeted the hardest specialties to acquire. “We did not get into cosmetic surgery or other specialties where the doctors would be keener to sign up,” Oliver explains. “We went to the primary care doctors, to the OBGYNs to the dermatologists where it’s actually very hard to get an appointment.”
The team went door-to-door across New York with a physical map marking doctor locations by specialty and insurance coverage. This revealed the true complexity: “Manhattan is not one market. It’s hundreds of markets, literally neighborhood by neighborhood, specialty by specialty, insurance by insurance. Nationwide we’re managing tens of millions of sub-markets and need to make sure we have supply and demand in harmony.”
That initial sales friction became defensible advantage: “We looked at this and said, okay, this is the friction. But that also means this will turn into a fantastic moat once we get to scale and build our brand. And it was just like that.”
For two-sided marketplaces, the question isn’t whether supply is easy to acquire—it’s whether competitors can replicate your hardest-won supply relationships.
Building Organic Growth Through Time Compression
Zocdoc’s 60% organic booking rate stems from a singular user experience contrast. “If you pick up the phone and dial for doctors, it takes on average 31 days to get an appointment with a primary care doctor,” Oliver notes. “On Zocdoc, you can do that same day.”
This 31x compression in time-to-value created what Oliver describes as “social currency in telling your friends about Zocdoc.” The result: minimal marketing requirements even 18 years in. “We luckily don’t have to spend disproportionately on marketing. Even though of course, now with our new model where we get paid for every incremental booking, it also does make sense for us to pay for marketing.”
The insight for product-led growth: organic sharing accelerates when your solution creates a before-and-after experience stark enough that silence feels like withholding valuable information.
Retention Through Mission Screening
Zocdoc hired their first sales rep seven months in. Eighteen years later, he remains at the company. Their chief communications officer has been there 14 years.
Oliver attributes this to what he calls hiring “squirrels” over “turkeys”: “You can teach a turkey how to climb a tree, but you’re better off hiring a squirrel. And Zocdoc is all squirrels all the way down. We are predominantly chosen as an employer by people that want to make a difference in maybe the most dysfunctional part of our everyday lives, which is healthcare.”
The retention mechanism: “When you buy into that as an important thing generationally to achieve, then you’re not going to be discouraged by some small setbacks.” Mission alignment functions as retention insurance through difficulty.
Even recent executive hires demonstrate this pattern: “We see this even with execs that have joined more recently. There’s obviously never a shortage of challenges. Covid was a huge challenge for us. We now are helping our clients overcome challenges that recent policy changes and regulatory changes are bringing for doctors. And because we have gone through hard times, we’re eager to help.”
The Time Horizon Reality
After 18 years, Oliver’s advice to healthcare founders distills to one word: “Patience.”
“Healthcare takes a lot of time. Set yourself up for something that you have the stamina and the breath to see this to the end. There’s so many overlapping issues. It’s very fragmented, it’s very regional, there’s lots of regulation. You have to work through all of these complexities and you have to do it in a way that you have the ongoing support of your investors and funders to be able to actually execute on your plan. If you assume it’s going to take a long time, that’s a very good assumption and act accordingly.”
Now, after years operating in what Oliver describes as defensive mode, Zocdoc is expanding beyond their core marketplace—powering insurance directories, embedding in Google and Apple Maps, and launching Zoho, an AI voice assistant that eliminates hold times by handling unlimited simultaneous calls.
“We are just now getting to the point where we can switch into this offensive gear,” Oliver explains. “Our brightest days are still ahead. The things that we actually set out to do, we’ve just really empowered ourselves to be in a position to execute.”
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