Matthew Prince
Analyst · JPMorgan
Thank you, Phil. Q1 was a quarter of contrast. We achieved revenue of $290.2 million, up 37% year-over-year. Our gross margin was 77.8%, again, above our long-term target range of 75% to 77% and up from 77.4% last quarter. During the quarter, we added 114 new large customers, those that pay us more than $100,000 per year and now have 2,156 large customers, up 40% year-over-year. Our dollar-based net retention fell to 117%, down 5% quarter-over-quarter. Importantly, we did not see elevated churn across our broad customer base. Instead, we saw a slower expansion from existing customers. More on that in a second.
Throughout this quarter of contrast, we saw tailwinds and headwinds. The reacceleration of our new business pipeline during the second half of 2022 continued again this quarter, and we meaningfully exceeded our pipeline plan for the second quarter in a row. Our win rate against the competition remained at record high levels, and renewal rates were consistent with the high levels experienced over the previous 4 quarters. Those were all positive signs.
On the flip side, the quarter saw new challenges, macroeconomic uncertainty, which intensified over the course of Q1 with every failing bank resulted in a material lengthening of sales cycles, a significant decline in close rates, even as win rates held strong and an extreme back-end weighting to the quarter. To give you some sense, almost half of the new business closed in the last 2 weeks of the quarter, which is very nonlinear for us. All of these factors put pressure on growth. The quarter most reminded me of Q1 of 2020 when businesses were paralyzingly nervous about the impact of COVID-19.
I think this parallel shows how with uncertainty in the economy, companies are closely watching their own businesses before committing to new spending. Thankfully, we continue to be a must-have, not a nice to have. And most of the deals we expected to close did, just later than we expected. I'm proud of our team's ability to sail through the rough seas that characterize Q1.
Although the current economy poses uncertainty for nearly every business in the near term, as Mark Hawkins and our Board likes to say, when the going gets tough, the tough get profitable, and we are tough. We have our hands firmly on the tiller of our business and are able to adjust to rapidly evolving market conditions in order to deliver operating profit of $19.4 million, representing a record operating margin of 6.7%. Furthermore, in spite of tougher collections in the quarter, particularly in the month of March, we generated $13.9 million of free cash flow, representing a free cash flow margin of 5%.
We continue to be on track to be free cash flow positive for 2023. As we navigate through the challenging macroeconomic seas facing our industry, this period of external uncertainty presents us with a perfect opportunity to be internally reflective, identifying areas of improvement within our business and taking proactive steps to create an even more successful and productive organization. As I take stock, we are not limited by the size of our market for our products, we are not limited by our ability to innovate, we are not limited by pipeline opportunity, and we are not limited by sales capacity. So what are we limited by?
As I said last quarter, Marc Boroditsky, our new President of Revenue, has dug into retooling our go-to-market efforts and identified significant opportunities to improve the efficiency and performance of our sales teams. Although we've won 1/3 of the Fortune 500 customers, if we're honest with ourselves, we saw a lot of our success with our enterprise customers because our products were so good and solved real problems that every big company faces. That allowed many on our sales team to succeed largely by just taking orders. When the fish are jumping right in the boat, you don't need to be a very good fishermen.
But at the risk of mixing watering metaphors, as the tide goes out, you get a clear view who's not wearing shorts. The macroeconomic environment has gotten harder, and we're seeing that some on our team aren't dressed for work. Digging in with Marc, we've identified more than 100 people on our sales team who have consistently missed expectations. Simply put, a significant percentage of our sales force has been repeatedly underperforming based on measurable performance targets and critical KPIs. That's obviously a problem.
But it's won in this environment with a particularly available and actionable solution. We are now in the process of quickly rotating out those members of our team who have been underperforming and bringing in new talent with salespeople who have a proven track record of success, grit and a strong cultural fit.
To give you some sense, these 100-plus people contributed approximately 4% of annualized new business sold over the last year. So we're optimistic we can make this team upgrade without significantly impacting sales capacity. While team upgrades are always hard, this is a uniquely good time for us to do this. A year ago, the tech labor market was extremely tight. Today, there is an abundance of talent eager to work at Cloudflare. In Q1, we received more than 0.25 million applicants, approximately 40% of which were for sales positions.
That's more applications than we received in all of 2021. In addition to the volume, the caliber of the applicants we're receiving is higher than we've seen at any point in our history, especially for go-to-market positions. While other companies are laying off, we're going to be bringing on great people with proven track records to raise the capability of our enterprise go-to-market team.
We've always had a culture of high performance at Cloudflare. However, with the value of hindsight, I think we and most other businesses got a bit soft during the COVID crisis around performance management. That was understandable at the time, but that time is over. The work we do is vitally important for the healthy functioning of the Internet. The opportunity ahead of us is massive. We have amazing people on our team who are executing every day to realize that opportunity, and we have an incredibly long line of other proven talented people looking to step in to fill the position where some of our current team aren't living up to expectations.
Our pace of innovation is not slowing down. Now more than ever, it's paramount we continue to innovate and develop unique offerings that deliver value to our customers and differentiate us from the competition. We are great at that. I want every dollar we put into Cloudflare to be more productive at driving revenue, profit and shareholder value. Innovation is a long-term competitive advantage, but productivity is too. Taking action to address inefficiencies in our go-to-market organization now will enable us to better capture new opportunities and expand our customer base and do so even more productively, profitably and predictably than before.
While I've talked about our team that's underperforming, that's only half the story. Our top salespeople are terrific. On average, the top 15% of our sellers have achieved 129% of quota over the last 4 quarters. They're incredibly consistent at bringing in new logos, expanding current customers and delivering results and approximately 27% of them started within the last 18 months. We know that if we hire the right people, they can ramp quickly and be successful with a full bag of products we handle.
In that spirit, let me tell you about some of the deals our top performers closed this quarter. A Fortune 500 media company expanded their relationship with Cloudflare, signing a 3-year $840,000 deal and bringing their total annual spend to $2.1 million. A customer of our application performance and security services since 2017, this company expanded into our Zero Trust portfolio with access and browser isolation for thousands of its contractors, displacing 2 Zero Trust competitors and even turning down 3 licenses from one of them. Cloudflare's products not only performed better than the competition during evaluation but we were the only company that could deliver on the complex requirements needed. This contract is only the tip of the iceberg with the customer, which plans to potentially roll Zero Trust out to all their tens of thousands of employees.
Responding to our descaler campaign, a leading e-commerce technology company in Europe expanded their relationship with Cloudflare signing a 3-year $780,000 deal. The company is going all in on Cloudflare One, Gateway, Access, CASB, DLP and Magic WAN. They were drawn to Cloudflare's platform as a unified pane of glass to consolidate their security modernization and network transformation needs, with Magic WAN as a key competitive differentiator versus first-generation Zero Trust competitors.
A global industrial machinery manufacturer expanded their relationship with us by signing a 3-year $648,000 deal. The company was looking to modernize their security infrastructure and is also going all in on Cloudflare One with Access, Gateway, Area 1 and Magic WAN, displacing multiple competitors. They appreciate being able to consolidate vendors, reduce costs and increase flexibility with Cloudflare's platform.
A Fortune 1000 SaaS company expanded their relationship with Cloudflare signing a 3-year $8.4 million deal. The company recognized Cloudflare's unique position as a neutral super cloud to manage and strengthen their application security posture and accelerated SaaS platform performance across AWS, GCP and their private data center environment. Additionally, no other solution could compete with our data localization suite to simplify the customer's global regulatory and compliance requirements. A leading IoT security company expanded their relationship with us, signing 2 3-year deals for a combined $4.2 million, one for its commercial business and a FedRAMP one for its government business.
The company has been a Cloudflare customer since 2020 using core application services and Cloudflare Tunnel for IoT devices. Drawn to our pace of innovation, this customer bought into the Cloudflare platform vision, now using over 25 products across core application services, Zero Trust and our developer platform, including R2, our object store and durable objects, combat high egress fees from AWS. They plan to use Cloudflare's FedRAMP authorization to scale operations on both commercial and federal sides of their business and increase their security posture.
A Fortune 1000 retailer signed a $1.3 million 46-month contract for Cloudflare's core application services to displace their existing vendor. They also added R2. The company has been dissatisfied with the unpredictability of their bills and bot-related issues from the current vendor and wanted to switch to Cloudflare, knowing our universal approach to protecting all traffic and our platform ease of use were top of the industry.
A leading gaming company expanded their relationship with Cloudflare, moving from a pay-as-you-go customer spending $200 a month to a contracted customer signing a 1-year $388,000 deal for R2, Workers and application services. The company was looking for a more scalable platform for storage and outperformance that would support their exponential growth. The customer realized that by moving to R2, they could eliminate egress fees they were incurring from the competitor, easily integrate with S3 APIs and centralized management. In particular, they were impressed with R2's lower latency and better throughput as well as how R2 tightly integrates with Workers and our core application services.
Traction among developers continues to be strong. We now have 4.92 million Workers applications running on our platform, up 146% over the last 6 months. 33,000 paying customers have activated R2 and are storing more than 7 petabytes of data, up 25% quarter-over-quarter. AI companies, large and small, continue to build on Cloudflare at a breakneck pace. When we ask them why, they cite our neutral position, rapid innovation and modern, nimble development environment. One last month called us "The first cloud infrastructure company built for the age of AI." I like the ring of that.
And I'm extremely excited about our upcoming announcement at Developer Week next month. We'll announce a lot around how we support AI and make any developer more productive. We are the best in the industry at innovation and we're making the changes we need to make and investing in our team to be the best in the industry of sales, too.
As I step back and think about what was a challenging quarter, I'm struck by our opportunity. We are not limited by the market for our products. We are not limited by innovation. We are not limited by pipeline opportunity. We are not limited by our ability to recruit. And we are not even limited by sales capacity. Instead, we are limited by our go-to-market performance. That's something we can fix, and we are committed to turning the current macroeconomic headwinds into a catalyst for positive change in growth at Cloudflare by investing in our top talent, refocusing on performance management and elevating the productivity of our team to seize the opportunity we have ahead, which we all know is massive.
With that, I'll turn it over to Thomas to walk through the financials. Thomas, take it away.