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.

Listen to the full podcast episode and review the transcript here.

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 Collison.

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.

Storytelling is everything that Ryan Wang was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here), where the most critical slides are highlighted.

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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.

Listen to the full podcast episode to know more, including:

• 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.

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