Christine Spang On Raising $175 Million To Build A Platform That Provides Universal Accessibility To Email, Calendar, And Contacts Providers With A Single Integration

Building a successful company is rarely a linear journey. For Christine Spang, co-founder and CTO of Nylas, the journey has been marked by significant pivots, bold decisions, and relentless perseverance when scaling the business and raising capital.

Nylas has attracted funding from top-tier investors like 8VC, Round13 Capital, Spark Capital, and Formation 8.

In this episode, you will learn:

• Christine’s journey shows that mastering complex concepts early on, like memory management and open-source software, laid the foundation for her technical expertise and entrepreneurial success.
• Nylas started as a productivity-focused email client but pivoted to an API infrastructure model, demonstrating the importance of adapting to market needs.
• Raising $175M required not just a great product but also strategic storytelling, investor alignment, and treating fundraising like a sales pipeline.
• Christine emphasizes that raising the right amount of capital for sustainable growth is more important than chasing the highest valuation.
• Early startup experiences at Ksplice gave Christine firsthand insights into bootstrapping, hiring, and navigating acquisitions—knowledge she applied when building Nylas.
• Nylas’ business model highlights how API infrastructure enables developers to build faster, integrate more efficiently, and scale their applications seamlessly.
• Christine’s advice to founders is to embrace uncertainty, take risks, and recognize their own agency in shaping the startup’s vision and success.

 

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About Christine Spang:

Co-Founder and CTO of Nylas, Christine Spang plays a pivotal role in the development and delivery of cutting-edge productivity-driven products and experiences for software developers and technical teams.

With a wealth of technical expertise and a passion for innovation, Christine leads Nylas’ technical strategy and works tirelessly to ensure that the company remains at the forefront of the industry.

Prior to founding Nylas, Christine worked at Ksplice and Oracle, where she served as a software engineer and principal developer.

During her time at these companies, Christine built technology designed to make Linux kernel security updates seamless, earning her a reputation as one of the brightest minds in the industry.

Throughout her career, Christine has remained committed to advancing the field of computer science. She holds a degree in computer science from MIT, where she honed her skills and developed a deep understanding of the industry’s intricacies.

Today, she continues to leverage her expertise to drive innovation and create world-class products that empower businesses and individuals alike.

As a child, Christine’s love for reading led her to become an avid reader and eventually led her to text-based adventure games, which sparked her interest in programming.

She became so engrossed in the game that she wanted to modify it, which prompted her to delve deeper into programming. By the time she was in high school, she was already contributing to Debian, a distribution of Linux, and had become deeply involved in free and open-source software.

Her fascination with MIT led her to pursue it as her dream school, where she eventually found herself involved in startups. She stumbled upon the startup world accidentally but never left it. The rest, as they say, is history.

Connect with Christine Spang:

• LinkedIn
• Crunchbase
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty, hello everyone, and welcome to the DealMaker show. Today, we have a very exciting founder joining us. We’re going to be talking about big pivots and the journey of raising money. On their end, they’ve raised $175 million.

Alejandro Cremades: We’re also going to be talking about the team and some of the core principles behind their culture that have driven their success. They’ve been pushing forward for over 11 years and counting.

Alejandro Cremades: Additionally, we’ll cover building, scaling, and financing. She was also part of an amazing startup tool right out of MIT, which ended up getting acquired by Oracle. This founder has seen it all. So, without further ado, let’s welcome our guest today, Christine Spang. Welcome to the show.

Christine Spang: Hey Alejandro, it’s really great to be here today.

Alejandro Cremades: Christine, you were originally born in Canada, but you weren’t there for long. Once you turned three years old, it was time to pack the bags and move to upstate New York. So, take us down memory lane. What was life like growing up for you?

Christine Spang: Yeah, for sure. Weirdly, I still have a fair amount of memories of being in Canada because my family would go back every spring break for a long time. I’d meet all the people I had lived on the same street as.

Christine Spang: I was born at Scarborough General Hospital, which, if you talk to people in Toronto today, they might call “Scarberia”—way on the outskirts, not really part of Toronto. My parents were immigrants; both were from Norway. My mother moved when she was in her tweens, and my dad came as an adult but was still fairly young.

Christine Spang: I remember having a little one-story house. I also remember going to the Scarborough Bluffs over Lake Ontario. Apparently, this area is really bougie now, but when I lived there, it wasn’t at all.

Christine Spang: I can understand why, though—having a cliff overlooking Lake Ontario could eventually attract people with money. When we moved to upstate New York, I don’t have super strong memories of the transition, but I remember living in a little apartment building with no furniture at first. Eventually, my parents bought a house in the suburbs.

Christine Spang: The reason we moved was that my dad got a job at Welch Allyn, a medical device maker. He was an electrical engineer. Before that, he worked for my grandpa, who made him promise not to leave Canada until he retired. My dad had always believed in the American Dream and saw the U.S. as a land of opportunity, but he had to wait. Once my grandpa retired, we were free to move, and we went to upstate New York for my dad’s job.

Christine Spang: I come from a pretty big family—I have three siblings: two sisters and a twin brother. Growing up, we spent a lot of time outside. Our suburban house had a big backyard with woods behind it. We built treehouses, made slingshots, and got into trouble in the backyard.

Alejandro Cremades: That’s always the way it is. But in your case, high school was when you discovered open source, which pushed you even further into computer science. You explored it even more deeply when you went to MIT. What was that moment like when you thought, “My God, this is fascinating”? How did that journey unfold?

Christine Spang: Yeah, for sure. I was always into science and math and knew I wanted to be some sort of engineer. But engineering is a broad area—are you going to build bridges or work with computers and create things with bits?

Christine Spang: In addition to spending time outside, I also read a lot of books, especially sci-fi and fantasy. I had a real thirst for adventure. Growing up in the suburbs felt very safe but also boring. As a teenager, I started getting restless. I channeled that into my mind and got into online adventure games called multi-user dungeons (MUDs). These were text-based games where you created a character and explored a world. I gravitated toward games with the fewest constraints because I wanted to create my own story.

Christine Spang: I got really into a Lord of the Rings-themed MUD and eventually started helping run it. The game had tools to create rooms and objects, but to change game mechanics, you had to learn to code. The game was written in C, which is not an easy language, but at 15, I decided I needed to learn C to modify the game.

Christine Spang: I vividly remember reading “The C Programming Language,” a classic book on C. I read the pointer section repeatedly. If you’re familiar with older programming languages, you know pointers and memory management are difficult topics. I remember being so confused about pointers until I read it enough times and talked to enough people that it finally clicked.

Christine Spang: The game also only ran on Linux, so I had to install Linux on the family computer. My uncle was a software engineer in the Linux ecosystem, which helped me make that connection. Over time, I started contributing to Linux itself. Through that process, I learned about MIT, the birthplace of open-source software. MIT became my dream school—this shining castle in my mind. I also watched “Good Will Hunting,” where Matt Damon plays a janitor at MIT who turns out to be a brilliant mathematician. That movie, along with encouragement from someone I met through Debian Linux and my high school friends, pushed me to apply. I was terrified, thinking MIT was out of my league, but I took my shot and got in.

Alejandro Cremades: What was the journey like at MIT, and how did it lead you into the world of startups and venture capital?

Christine Spang: Honestly, MIT was great for me. It was the first place I felt like I had truly found my people. In high school, I had music geek friends, but at MIT, everyone was a super nerd. It was a place where all the weird things I did weren’t weird—they were appreciated. It was cool to be into the things I loved.

Christine Spang: But MIT is also an intense place. Everyone who gets in was the smartest person at their school. Then you arrive and realize you’re not the smartest anymore. The classes are harder, and you actually have to work to succeed. I had to learn how to take care of myself—eating well, getting sleep, managing stress.

Christine Spang: I got involved in the computer club, where I met people working on a technology that turned into a company called Ksplice. It was a service for updating the Linux kernel without restarting the computer. The founders commercialized it as a security update service, particularly useful for web hosts and VPS providers, where timely security updates are crucial.

Christine Spang: One of the founders and I had crossed paths through Debian Linux, where I was an official project contributor. He mentioned they were looking for interns, and I was instantly interested. At the time, there weren’t many startups coming out of MIT, at least not 15 years ago. It had a lot of buzz among the computer science students.

Christine Spang: I started working at Ksplice part-time during my senior year and eventually had to decide whether to stay for grad school or take a full-time job offer. I had never been passionate about staying in academia. I’m more interested in applying techniques rather than discovering new ones. I work best in a team, I’m practical, and I like seeing the results of my work quickly. So, even though I had considered staying for a master’s degree, the decision was easy. I took the job at Ksplice and got paid to build something.

Christine Spang: The email app was designed to be a desktop application where everything would happen. The idea was that people would build extensions into the email app, making it the central hub of user experience. Long story short, we built the API infrastructure to power the app, but ultimately, the email app itself turned out to be a dead end. It’s incredibly difficult to build an email application that people are willing to pay for.

Christine Spang: People are accustomed to email being subsidized by major tech companies, and the bar for features in such an app is extremely high. Our thesis was that users would build productivity extensions within the app for functions like customer support or sales, but this assumption proved to be entirely incorrect.

Christine Spang: We discovered that people don’t want to outsource their end-to-end user experience to someone else or be part of another company’s app. Instead, they want to create exceptional experiences within their own applications—experiences they can control and that drive engagement directly to their platforms.

Christine Spang: We spent four years building the foundation for this infrastructure. In the process, we also developed the desktop app, which ultimately required a major pivot. Running the app was hemorrhaging money, and churn was extremely high. It became clear that the app was not going to evolve into a scalable business. As a result, we had to shut it down and spin it off as an open-source project.

Christine Spang: We then refocused on the part of the business that was working—the API infrastructure that had powered the app. This allowed developers to use our infrastructure to integrate communications data into their own applications and experiences.

Christine Spang: Developers use our features to drive engagement and provide compelling functionality within their own apps, where they maintain control over the full user experience.

Christine Spang: This was a truly existential moment for us. If we had continued on the same path, we would have run out of money. It was evident that the original approach was not working.

Alejandro Cremades: Obviously, you took action and turned things around. For those listening, can you explain the final business model of Nylas? How do you generate revenue?

Christine Spang: We operate as an API infrastructure company, similar to Stripe or Plaid. We sit between applications and the underlying cloud infrastructure that developers use to build software today.

Christine Spang: Essentially, we have built integrations with various communications data providers, including all major email and calendar services.

Christine Spang: Additionally, we develop customizable user experience components that correspond to common workflows. These workflows are essential for many businesses, and our infrastructure allows them to go to market more quickly.

Christine Spang: We provide the core functionality that companies need to build competitive apps without having to develop these components from scratch. While these features are necessary, they do not differentiate one app from another. For example, every CRM or business productivity app requires email and calendar integrations, embedded scheduling, and contact management. Today, AI agents also need access to this data to personalize their actions and recommendations.

Christine Spang: Our platform acts as a middleware layer that accelerates development and reduces operational overhead. My team specializes in email connectivity and the complexities of calendar integration, ensuring that our customers don’t have to handle these technical challenges themselves.

Christine Spang: Our customers pay based on usage. They connect end-user email and calendar accounts to our platform, and we bill them monthly based on the number of connected accounts.

Alejandro Cremades: Got it.

Christine Spang: Our model works in a complementary way—customers typically start small. We have a self-serve platform where users can sign up and start paying as little as $30 per month to access our full capabilities. As their apps grow and gain users, our revenue increases in parallel. Many of our customers expand significantly over time because our product is highly sticky; it powers essential functionality within their applications.

Christine Spang: We see our role as a long-term partner for companies building on our platform. Our goal is to help them navigate the constant changes in the software world. Today’s application developers must integrate with numerous data sources, and user experience expectations are always evolving.

Christine Spang: Over time, applications are replaced by newer generations that better meet user expectations. Companies must keep pace with these changes to remain competitive. Our job is to track these evolving expectations and provide the essential building blocks so that developers can focus on their core differentiators and customer needs.

Alejandro Cremades: Building a company like this and delivering such an experience requires capital. Up until now, you’ve raised $175 million. How has the fundraising experience been for you?

Christine Spang: Our first funding round was at the end of 2013—a small seed round of around $2 million. Since then, we’ve raised multiple rounds over the past decade.

Christine Spang: Our most recent round was our Series C in 2021, where we raised $115 million. Most of that capital has been invested in R&D and product development.

Christine Spang: The fundraising landscape changes with each stage. At the seed stage in 2013—during the peak of the zero-interest-rate era—investors were more willing to fund ideas. There was an abundance of capital in the system, allowing for greater flexibility.

Christine Spang: However, at the Series A stage, investors expect to see demonstrated demand and a capable team. In later rounds, it becomes all about metrics—growth rate, revenue, and scalability. Investors want to understand how capital will be deployed to accelerate growth.

Christine Spang: Fundraising is essentially a business pitch, not just a technology pitch. At early stages, investors may focus on the product, but as the company matures, the emphasis shifts to business growth and scalability.

Christine Spang: For every funding round, I maintained a VC CRM—a spreadsheet of target investors categorized into tiers. We approached certain investors early to refine our pitch before targeting higher-priority firms. It’s a sales process, and creating a sense of competition can improve fundraising outcomes.

Christine Spang: One key lesson I’ve learned is that maximizing valuation isn’t always the best strategy. The critical question is: How will the capital be used, and how far will it take the business? Between 2010 and 2020, the mindset was often about raising enough to reach the next funding round. Today, companies are shifting toward raising capital to achieve self-sufficiency.

Christine Spang: Founders raising money today should focus on achieving financial independence rather than being trapped in a cycle of constant fundraising. Investor expectations have shifted significantly.

Christine Spang: AI has demonstrated that businesses can scale in different ways. Some vertical applications grow rapidly with minimal capital, while others—such as core LLM providers—require massive funding but experience exponential growth.

Christine Spang: Fundraising strategies from five or ten years ago may no longer be effective today. The landscape is constantly evolving, and founders need to adapt their approach accordingly.

Alejandro Cremades: I completely agree. Investors are betting on the future. If you could wake up tomorrow in a world where the vision of Nylas is fully realized, what would that world look like?

Christine Spang: Our vision is to make people more productive, enabling them to focus on meaningful work rather than spending excessive time in front of computers managing workflows.

Christine Spang: We aim to modernize manual workflows. One of the first use cases for Nylas was integrating email data into CRMs. Early CRMs required users to BCC a special email address to capture conversations, but this was inefficient—people often forgot to do it, leading to incomplete data.

*****

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