He Raised $71 Million To Provide Companies With An AI-Powered Customer Support Platform That Integrates WFM And AI Agents
Ryan Wang is building in one of the most consequential layers of modern software: the operational infrastructure that allows great ideas to scale without breaking.
As the co-founder and CEO of Assembled, Ryan sits at the intersection of customer support, AI, and organizational design, an area most companies only confront once growth exposes their cracks.
But Assembled didn’t emerge from a contrived startup thesis or a trendy pitch deck. It grew out of lived experience, deep obsession, and years spent watching what happens when founders care deeply about customers but lack the tools to scale that care.
In this exciting interview, Ryan talks about his experiences with building his company, raising capital, and choosing lesser-known names in the venture capital circuit for their Series A and B rounds. He also reveals insights about “building a startup inside of a startup,” as he terms it.
Growing Up in Chicago: Immigrant Roots and Midwest Grit
Ryan was born and raised in Chicago, the son of immigrants from coal country in Shanxi, China. Chicago shaped him in ways that would later become foundational to his worldview—gritty, humble, and grounded.
“It’s a cold-weather sports town,” Ryan recalls. “You root for the Bears. You root for the Bulls. It’s not glamorous, but it’s real.” That Midwest sensibility stayed with him even after he moved west.
When Ryan arrived in Silicon Valley in 2014, the contrast was jarring. The optimism, the self-promotion, the speed; it was a cultural shock for someone raised in a place where hard work speaks louder than ambition.
A Transformational Education at IMSA
One of the most defining chapters of Ryan’s life began at the Illinois Mathematics and Science Academy. IMSA is a public boarding magnet school founded by Nobel laureate Leon Lederman, who also ran Fermilab (Fermi National Accelerator Laboratory) for a while..
IMSA wasn’t just academically rigorous; it was philosophically different. The school emphasized self-directed learning, intellectual curiosity, and research over rote instruction. Wednesdays weren’t spent in class; students pursued independent research projects instead.
Before IMSA, Ryan admits he spent much of his time playing video games. After IMSA, he became a self-driven learner, a shift that would echo throughout his career.
One formative experience involved emailing every economics professor at the University of Chicago in search of a research mentor. Only one responded: Emily Oster, then a second-year assistant professor. “She didn’t have to say yes,” Ryan says. “But she did.”
That generosity left a lasting impression. Oster would later become a world-famous author, but to Ryan, she remains an early example of someone who saw potential before it was apparent.
Consulting, Freakonomics, and Falling in Love with the Real World
Ryan initially planned to pursue graduate school in economics or statistics and got his BAMS degree. Consulting was meant to be a temporary stop and a way to gain experience before returning to academia.
Instead, Ryan landed at a decidedly unconventional consulting firm run by Steve Levitt (author of Freakonomics) and Daniel Kahneman (author of Thinking, Fast and Slow). The work wasn’t theoretical. Ryan anticipated learning how theory is applied in the real world, but liked what he did
Ryan was building data-driven pricing algorithms for some of the largest retailers and automotive companies in the world. For the first time, he saw how abstract models shaped real-world outcomes.
“That’s when I realized I didn’t want to stay in theory,” he says. “I liked the messiness of reality.”
Joining Stripe Before Stripe Was Stripe
A consulting project in payments and a timely introduction through his brother led Ryan to Stripe in 2014, when the company had fewer than 100 people. Suddenly, right out of his consulting stint, he was in Chicago getting introduced to Patrick C ollison.
Even during interviews, something felt different. The talent density was extraordinary. At the time, Ryan “was not plugged into the Silicon Valley atmosphere.” But he realized that every single person on the panel who interviewed him was incredibly smart and driven.
Michael Manipat, Ryan’s first manager and boss, held a PhD in math. He had studied genetic algorithms applied to economics and later became CTO of Notion, which Sequoia backed. Daniela Amadei, Ryan’s recruiter, would go on to co-found Anthropic.
One of Ryan’s onboarding sessions was led by Greg Brockman, then Stripe’s CTO, later the co-founder of OpenAI. Surrounded by so many interesting people, Ryan loved being a part of the intellectual environment. Little did he know that it would later become the impetus for Assembled.
The Unusual Recruiting Strategy
Stripe didn’t just hire impressive résumés. It hired for trajectory. Ryan, who had never formally studied computer science, received an offer titled “Software Engineer.” “They looked past what was on paper,” he says. “They cared about how fast you could grow.”
Ryan joined Stripe at a time when founders Patrick and John Collison were still personally rotating through customer support, sometimes hosting support sessions out of their apartment. As Stripe scaled from 80 to 800 employees, the intimacy of that model became impossible to maintain.
Yet the importance of customer support never diminished. Ryan considers himself lucky to have been one of the first 80 people. He saw firsthand how hard it was to preserve founder-level care at scale. Stripe is one of the most successful companies today that hasn’t gone public yet, as he underscores.
Talking about the core reasons behind Stripe’s phenomenal success, Ryan alludes to exceptional talent density. Its cofounders were open to hiring people from diverse and “wacky” backgrounds.
Greg himself was a college dropout, but was recruited because he was the “smartest person at MIT who moved to Harvard.” Mike Moritz hired Ryan and his brother, who hadn’t yet graduated from college. The Stripe recruiting philosophy was decidedly unusual.
They'd rather hire super high-trajectory young people with weird backgrounds and creativity than just go for experience. Essentially, they were bringing in people with incredible pristine backgrounds.
Customer Support as a First-Class Problem
Ryan could have imagined remaining at Stripe for a long time, but then he started obsessing over the customer support problem. He came from a machine learning background in fraud detection.
Eventually, in 2016, Ryan, along with John Wang and Brian Sze, his future co-founders, began asking an unusual question: “Why isn’t anyone applying machine learning seriously to customer support?”
They initially focused on automation and building systems to deflect tickets using early ML models long before modern AI. Around this time, the trio built the Lumos system.
Ryan and his team intended to hand-tune the models and automate a significant portion of ticket volume. However, Bob Van Winden, Stripe’s head of support, delivered a pivotal insight: “Ticket volume isn’t the real problem. Productivity is.”
That realization led them to workforce management—forecasting demand, scheduling thousands of agents, and optimizing human effort at scale. It was the least glamorous part of customer support, and the most mission-critical.
And that’s how Ryan and his cofounders ended up building Assembled’s first product. It was the software Stripe needed to buy that just wasn’t available out there.
Founding Assembled: Obsession Over Optionality
What began as an internal project at Stripe became an all-consuming obsession. Ryan and his co-founders observed the same pattern across fast-growing companies such as Slack, Robinhood, Grammarly, and GoFundMe.
The trio realized that there’s a lot of breadth to the machine learning challenges they needed to forecast. They were solving some version of the nurse scheduling problem and building schedules for thousands and tens of thousands of people at a time.
Founders cared deeply about customers and customer experience. However, accelerated growth broke their systems, and spreadsheets collapsed under complexity. At that point, starting Assembled wasn’t a career move; it felt inevitable. “It wasn’t even a choice,” Ryan says. “We just had to do it.”
Building a Multi-Product AI Platform
Explaining the Assembled business model, Ryan reveals that today, it is a comprehensive AI platform for customer support. The company has been operating for 8 years and offers several products, including AI agents.
These AI agents handle chat and voice calls. For instance, when users contact Patreon, Etsy, Canva, or other iconic companies, they interact with Assembled’s chatbots. It also provides AI copilot tools that double agent productivity and ramp up speed.
Assembled also offers workforce management for forecasting, scheduling, real-time operations, and capacity planning across humans and agents. It’s a form of hybrid orchestration between humans and AI. While these are some of the core products, Assembled has others too.
As Ryan explains, they offer “everything under the sun in terms of support operations.” The pricing reflects that maturity: headcount-based for core operations and usage-based for AI automation. Eight years in, Assembled is no longer a single-product company; it’s an operating system.
Product-Market Fit Is Not Permanent
Talking about nailing their product-market fit, Ryan reveals that it had a lot to do with the market and what was happening in the world. Assembled had officially launched in March 2020, just as COVID shut the world down.
Their Hacker News debut sat between headlines announcing a global pandemic. It should have been disastrous. Instead, it became catalytic. Remote work exploded. Distributed support teams became the norm. Companies desperately needed tools to replace fragile spreadsheets.
And Assembled was replacing these spreadsheets. Companies like Robinhood, Slack, Casper, GoFundMe, and Grammarly were blowing up and became early adopters. Their support teams were growing fast because their businesses were also growing fast.
That was Assembled’s first product-market fit. The second came in 2022, when many of these companies faced headwinds and had to become more efficient. Their headcount growth slowed, and efficiency mattered more than expansion.
Assembled had to reposition from growth enabler to ROI engine. It wasn't just riding headcount growth; it was about making their teams 20% to 30% more efficient.
The third arrived with AI. As Ryan points out, the fact that customer support is obviously an AI application is an open secret. Rather than launching generic chatbots, Assembled built resource-aware AI agents on top of its workforce management data.
These were systems deeply integrated with workforce data that intelligently balance human and AI labor; they were entirely different from any other chatbot. Ryan concedes that it took them some time to figure out what customers needed.
Their solution was to go back to them and discuss what needed to be tweaked and refined. Ryan and his team worked on the tools for a year and a half before launching. As he explains, each wave required reinvention. Each time, product-market fit had to be earned again.
Raising $71M and Choosing the Right Partner
Assembled has raised $71M across Seed, Series A, and Series B. Coming out of Stripe made fundraising easier but also riskier. Ryan and his team faced a surplus of term sheets, brand-name firms, great partners, and exciting conversations. However, they were able to vet people thoroughly.
What stood out wasn’t prestige. It was persistence. Ryan and his cofounders were looking for people who knew about and cared about the space. Emergence Capital showed up uninvited, deeply prepared, and intellectually engaged.
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They pushed the founders’ thinking and demonstrated real domain understanding. Further, Emergence is a top B2B SaaS investor and one of the first backers of Zoom and Salesforce. Their track record was impeccable, and engineers in Silicon Valley typically care about brand recognition.
Ryan admits he initially leaned toward flashier names. But the decisive question became: “Who will still be here when things get hard?” When the zero-interest-rate era ended, and markets turned, Emergence stayed. The same partner. The same support.
Years later, they remain deeply involved in hiring, strategy, and execution. “Easy come, easy go is real,” Ryan says. “The best partners compound.” He recalls how all they had to do was send them a data room, and the next day, Emergence would give them a term sheet.
What Real VC Value Actually Looks Like
For Ryan, value isn’t vague advice; it’s operational leverage. For instance, Jake Saper, a board member, led the Series A round from Emergence. He offers hands-on help in recruiting executives. Then there’s Tammy Hahn, a talent partner who has provided valuable lessons in recruiting over the years.
Ryan also gives a shout-out to Doug Landis, who was an early go-to-market partner. Doug helped Ryan set up a sales quota and understand how the ratio of Account Executives (AEs) to Sales Development Reps (SDRs) works.
Assembled has also benefited from board members who have been willing to challenge Ryan directly. One of Ryan’s most meaningful moments with his lead investor was a two-hour phone call where they argued intensely about the company’s direction. “That only happens if there’s real trust,” he says.
A Bigger Vision: Scaling What Comes After Big Ideas
Ryan describes customer support as the gap between mission and reality. His vision is about embodying the idea that there’s a difference between building an initial great product and scaling it to reach hundreds of millions, if not billions, of people.
For instance, Robinhood’s mission was to make investing accessible to everyone. That mission became real only after they added 24/7 phone support. Ryan recalls communicating with them in 2020, around the time Bitcoin and meme stocks were blowing up.
He convinced the folks at Robinhood that Assembled could close the gap not just in support, but across all operational challenges that emerge once ideas scale.
Ryan often compares this to aviation. Flight was invented over a century ago, yet scaling it to billions of people required massive operational systems. Delays, staffing, or logistics; none of those problems negate the idea. They expose its complexity.
As Ryan points out, “Support is just one piece of the operational challenges, but there are lots of others that companies run into when scaling.” Assembled aims to be the technology that makes scaling possible.
Advice to Founders in the Trenches
Ryan doesn’t sugarcoat it. It will take longer than you think, he tells aspiring entrepreneurs. Ryan and his cofounders thought their first big idea would be a hit. But it took them eight months to reach their first dollar in revenue.
Ryan also cautions that product-market fit will fade, and founders have to recommit again and again.
What matters is choosing a problem they can stay obsessed with for decades, not a solution, not a trend, but a durable challenge.
Assembled now has four products, and Ryan and his team are already thinking about what goes beyond workforce management, customer support automation, and even AI for customer support. They are thinking about how things will be 20 years down the line.
“AI won’t be the thing forever,” Ryan says. “But scaling big ideas will always be hard.” That is the problem Assembled is built to solve. And that is why Ryan is still all in.
Staying Grounded Through a Global Perspective
Half of Assembled’s end users live outside the United States, in places such as India, the Philippines, the UK, South Africa, Ireland, and Ukraine. One of Assembled’s early customers, Grammarly, was founded in Kyiv but later moved to Canada. Ryan visited Ukraine in 2019 to meet support managers there.
Years later, after the war began, one of those managers spoke at an Assembled all-hands meeting in San Francisco. She had traveled by train through Poland. Her husband couldn’t leave Ukraine. “That moment put everything into perspective,” Ryan says.
Euphoria and terror are part of entrepreneurship, but impact is about people from across the world, from different walks of life. It’s about giving a platform for what they do and helping them pursue their dreams and passions. That awareness keeps him grounded.
Ryan Wang built Assembled to solve the unglamorous scaling gap between a company’s mission and the operational reality of supporting customers at a massive scale. · Stripe’s early edge came from extreme talent density and a willingness to bet on high-impact people with “wacky” backgrounds rather than pristine résumés. · Assembled started as “a startup inside a startup” at Stripe, where customer support was treated as a first-class product problem, not a back-office cost center. · The breakthrough insight was that automation alone doesn’t solve support; workforce productivity and capacity planning (WFM) drive the real cost and handle-time leverage. · Product-market fit isn’t permanent; Assembled had to reinvent through COVID-driven distributed work, the 2022 efficiency reset, and the AI wave. · The company’s differentiation is an integrated platform—resource-aware AI agents plus WFM—so decisions about what AI handles versus what humans handle are operationally optimized. · Raising $71M reinforced a key fundraising lesson: the “best” investor is the one who compounds with you in hard markets through hands-on hiring, GTM rigor, and honest board-level pushback.
Original Version
Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMaker show. So today we have an amazing founder, you know, a founder that is building in a really exciting segment right now. You know, everyone is really all about customer support, customer service. I think that they're nailing it and they're building a rocket ship. We're going to be really talking about some interesting stuff. So brace yourself for a very inspiring conversation. Whether it is raising money, building your business, how they went about picking lesser known names, you know, on on VCs that they were working with. And again, they did that for the Series A and for their B round. But, you know, you're going to see, you know, why they went about doing it that like that. And also building a startup inside of a startup.
Alejandro Cremades: I mean, so really, really good stuff. So again, brace yourself. And without further ado, let's welcome our guest today, Ryan Wang. Welcome to the show.
Ryan Wang: Yeah. Thanks for having me, Alejandro. Really good to be here.
Alejandro Cremades: So originally born and raised in Chicago, you know, parents, immigrants from China. So, you know, I'm sure it was an amazing, you know, upbringing and we'd love to hear how was life growing up for you?
Ryan Wang: Yeah, I i think um there's something about growing. so my parents are from coal country, China. So Sanxi. ah um And Chicago, I feel like, you know greedy, you know,
Ryan Wang: a lot of people that come from there from the Midwest generally, i think, um ah you know, probably really resonate with that feeling.
Ryan Wang: And so, ah yeah, I grew up in, in rooting for the bears, rooting for the bulls.
Ryan Wang: The bulls were very good when I was younger and then not so good, you know, later on, but, you know, cold weather, sports town, you know very humble, ah kind of grity greedy type of place. And and and so when i when I came to Silicon Valley, that was 2014 or something like that. it was it was It was a bit of a culture shock in many different ways.
Ryan Wang: I would say of the fun parts as well about growing up in Chicago There was a very interesting educational experiment that they ran. So I went to this high school called the Illinois Math Science Academy.
Ryan Wang: It's a public boarding magnet school. And it was started by this guy, Leon Letterman, who won a Nobel Prize. He ran Fermilab for a while. And it was just magical place for me and it kind of got me going a of different ways.
Ryan Wang: Before then, I was playing a lot of video games and after that, kind of became much more of a student, you know kind of self-driven learner, which was kind of the whole philosophy of the school and um has really paid me have paid me back really, really well.
Ryan Wang: and And it continues to be an institution I really support. like So public boarding magnet schools in Illinois.
Alejandro Cremades: No kidding. Now, now, now, one thing you know there is that one of your teachers, you know, Emily ended up becoming quite the quite the author.
Ryan Wang: That's right. Yeah. Yeah. Emily Oster. um ah so So the school had a a a bit of a kooky approach to education. Again, it was very self-driven. So Wednesdays, you didn't have school. You'd go do a research project.
Ryan Wang: And so to to go find a research project, i myself and my friend, ryan also Ryan, who was my partner back then, you know in terms of like this project, we emailed every single ah economics professor at UChicago.
Ryan Wang: And Emily was the only one to respond. And she was a second year assistant professor or something like that. I don't know how she found the time ah you know to mentor us on their research project. And then at the same time, churn out research. And then, um you know of course, later on becoming world famous author, Emily Oster. And um I'll just say that she's an amazing person and incredibly generous and and and saw something in us that maybe we didn't even know at the time.
Alejandro Cremades: And why consulting out of all things to get going in the your career?
Ryan Wang: Honestly, consulting, i i I thought I was going to go to grad school. I thought I was going to go be an economist or a statistician. I got BAMS in economics and statistics. and um It was just something to be in between, you know get a little bit of experience and then go back to research.
Ryan Wang: I ended up working at this kooky consulting company. It wasn't like a normal one.
Ryan Wang: It was run by Steve Levitt, the Freakonomics author, and Danny Kahneman, um the Thinking Fast and Slow author. and um Again, I went there thinking that, okay, I'll i'll learn some of how ah you know the theory is applied out in the real world and realized, you know what, actually I really like the real world and consulting with companies and building data-driven pricing algorithms for for some of the biggest retailers in the world um and biggest car companies in the world. and and then i And then I was hooked. And then from there, ended up going straight to Stripe because we had done um a consulting project around payments. We were working with one of the biggest payments companies in the world. And then simultaneously, my brother was was about to join Stripe and and and they had recruited him right out of MIT. So um two things, you know, kind of at two points kind of connected to a line is, oh yeah, can you introduce me to Stripe? And um he did. And he introduced me to Patrick Carlson, and who I didn't know much about at the time. Again, I was just in Chicago.
Ryan Wang: Like, oh, cool. yeah Yeah. I'll just talk to Patrick and and um and and And then you know they ended up finding a place for me.
Alejandro Cremades: I mean, that was 2014, so it was a different stripe.
Ryan Wang: ah I think when Even when I was interviewing, i could tell that there was something special going on. And again, I was not plugged into the Silicon Valley um you know atmosphere. So when when I saw special, it was ah you know the first person on my team who interviewed me, like he his name is Michael Manipat, and he had a PhD in math. and But he had studied kind of ah economic like genetic algorithms applied to economics.
Ryan Wang: And ah he was the it was my first boss and just kind of the range, the intellectual range was incredible. He later became CTO of Notion and ah you know has now founded his own company backed by Sequoia.
Ryan Wang: So you know just an incredible person. And back then it was just, wow, like you're so smart. It's so driven and like I want to be around you. and And every single person on my interview panel was kind of like that.
Ryan Wang: like my recruiter. The recruiter was Daniela Amadei. She happens to now be you know co-founder president of a company called Anthropic that everybody knows about. So it's just you know the talent density, um ah the ideas. and And just, it wasn't even, ah you know it was like,
Ryan Wang: So we went to Kyiv in 2019 and met all these people—these customer support managers—and got to know them.
Ryan Wang: And then, of course, after that, what happened was just devastating. We kept in touch with folks. And even, I want to say a year ago, one of the managers came to San Francisco and came to speak at our all-hands.
Ryan Wang: I remember taking a walk with her and one of our sales folks. And I asked, so, did your husband come with you? She said, no.
Ryan Wang: She had to take a train to Poland to then fly here, and men aren’t allowed to leave the country. I was like, wow. That puts all of this into perspective.
Ryan Wang: We want to be great. We want to have a big impact. And impact is working with people from all across the world, from all different walks, and giving a platform for what they do.
Ryan Wang: Now she’s started a company. And every day they’re living. They’re just living. There’s everything that’s going on, and they’re pursuing their dreams and their passions.
Ryan Wang: I was like, damn, I am so inspired by that. And for us to be a small part of that—our problems seem small. The euphoria, the terror—that’s more about a scoreboard that somebody else is keeping.
Ryan Wang: We’re talking about impact. And that keeps me grounded—just knowing who we’re working for.
Alejandro Cremades: I love that. So Ryan, for the people listening that would love to reach out and say hi, and learn more about Assembled too, what’s the best way for them to do so?
Ryan Wang: Yeah, I’m on LinkedIn. I’m Ryan Wang. I write about the future of work and connecting support and AI.
, especially if you are a talented engineer, a talented entrepreneur, and you just want to chat.
Alejandro Cremades: Well, Ryan, thank you so much for being on the DealMaker Show today. It has been an absolute honor to have you with us.
