Building the Future: April Underwood's Take on Slack and AI Startup Dynamics
Last fall I caught up with former Slack CPO April Underwood during a panel at TechCrunch Disrupt where we spoke about product-market-fit. April and I have a long history: she passed me the reins to become Slack’s CPO in 2019. We had such a great time chatting about the early days of Slack that I wanted to dig deeper. So, I invited April to join me for a conversation about applying her experiences working at Slack to today’s new AI ecosystem.
Today, April is the managing director and co-founder of Adverb Ventures, an early stage venture firm that’s backed companies including Particle, Outset, and CoveAI. As a co-founder of the investing collective #ANGELS, she has also personally invested in more than fifty companies including Vanta, Color, and Shotsy.
April and I discussed the secret behind how Slack became such a pivotal company as well as its ongoing impact on online curation and search. We also talked about April’s work as an investor and the effect that AI is having on early stage companies. Below are the key takeaways from our conversation.
Here’s what Slack got right early on
It had a sticky product that appealed to tech users: Even in Slack’s earliest days, it garnered a lot of enthusiasm across the tech industry. April saw this firsthand when her former Twitter colleagues suggested moving their daily text conversations from iMessage to Slack — and never looked back. “When you see industry insiders with the highest bar for product quality using a product every day, it’s a good signal that you want to jump on it — as an investor and a builder.”
It solved a fundamental workflow problem: Slack understood what email got wrong. Unlike email, which forced users to sift through cluttered inboxes, Slack introduced the concept of channels, which was an intuitive way to structure discussions around projects, teams, or shared interests - a novel user experience at the time. This approach gave users more control over how they engaged with information, making workplace communication more relevant and accessible. It’s a feature that continues to be deeply relevant today.
Slack took an “artisan” approach to product building: One word that April remembers Slack founder Stewart Butterfield using frequently is “craftsmanship:” “This was not a word I had heard in organizations prior to working at Slack,” she told me. “Craftsmanship represented the care and concern in how we thought about the job we were doing. We weren’t only rational product thinkers; we thought of ourselves as artisans. We talked a lot about building a product that we would want to use.”
It had a clear roadmap: April recalled one of the earliest Slack decks she ever saw, in which Stewart laid out his long term plans for Slack, even as it was in the midst of pivoting from a gaming app into the work management tool it is today. “He always had a long term vision for the company that was clear to understand,” she said. “Having that North Star makes a huge difference in terms of teams picking the right things to work on and working on them to a quality that everyone was proud of.”
It capitalized on product integration: Search is core to Slack’s business. The company’s name is an acronym that stands for “Searchable Log of All Communication and Knowledge.” This is why it was key that Slack integrated early on with other SaaS tools like Google Drive, GitHub, Box, and Dropbox. “We offered a search experience in Slack that searched not just the contents of conversations within Slack, but also the underlying content with the files from those major file sharing services,” said April. “This was a hugely powerful feature.”
What made this approach so powerful was that it ensured that Slack became a key part of its customers’ infrastructure. “Over time, we continued to build Slack to be more open so that developers could build on top of it. This meant that we were bringing in the most relevant information and workflows from any application into the channels where employees spent their time,” said April.
Investing as a VC in AI in 2025
Today, April is applying the lessons she’s learned building companies like Slack and Twitter to her work as an early stage investor. Generative AI has significantly ramped up the pace of innovation compared to the early days when April was overseeing product at Slack. It's also having a big impact on the way that early stage companies are being built. These are the effects that April sees AI having on early stage companies right now:
AI is commoditizing the creation of software: “Today, you’re betting on a new set of priorities when it comes to giving a team an opportunity,” said April. “If you believe that all of the foundation models will eventually converge, then at some level everything becomes about the application layer. You want to bet on companies that really understand their customers and their customers’ workflows. More so than ever before, companies need to have an advantage when it comes to distribution.”
AI flattens minor advantages: Gone are the days when engineers could work exclusively on one operating system for their entire career. “You no longer work only in iOS or only in Android — AI enables you to do both,” said April. “In the past, it would have been unthinkable for a small team to have apps on both platforms but with Copilot and ChatGPT, you can get these products built much faster. I love working with founders who use these AI tools to flatten the advantages that other teams with more people or more capital may have.”
And it’s making startup teams smaller: “If you’re starting a company in 2025, you're not only thinking about generative AI’s impact on what you build, you're thinking about its impact on how you build,” she said. “When you marry macro workplace trends like fractional work with these new generative AI tools, your average startup team starts to look very, very different. For one, the teams are smaller. On top of this, they have a completely different staffing model and they rely more and more on AI tools.”
This is true for some of the teams that April recently backed, including a consumer startup which reached a six-figure ARR in only a few short months. The team is made up entirely of one full time founder and three employees who work part time. “Today you can imagine outcomes where teams that are a 10th of the size of a traditional Series A company are achieving just as much as companies that got started only a few years before them,” said April.
Thanks for reading, and thanks again to April for taking the time to chat with me.
Tamar