‘SaaS AI’ the Industry’s Next Chapter... Insights From SaaStr 2025

To understand how Silicon Valley’s SaaS companies are preparing for and responding to the AI era, I attended the SaaStr Annual 2025 conference, held May 13–15 in San Mateo, California.

As the world’s largest Software-as-a-Service (SaaS) community, SaaStr brings together founders, executives, and investors to exchange ideas, strategies, and insights.

This year’s event offered a timely look at how global SaaS players are navigating AI-driven transformation—redefining product roadmaps, customer engagement models, and growth strategies in real time.

In this piece, I outline the key trends that emerged from the conference and explore what they mean for SaaS leaders in Korea, where similar challenges—and opportunities—are rapidly taking shape.

At this year’s SaaStr Annual conference in San Mateo, Silicon Valley's leading SaaS companies—including OpenAI, Anthropic, Box, and HubSpot—took center stage. Executives such as Box CEO Aaron Levie, HubSpot CEO Yamini Rangan, Gusto founder Joshua Reeves, and Perplexity’s Chief Business Officer Dmitry Shevelenko offered an unfiltered look into how they are navigating the AI transition.

The most valuable part of the conference was hearing directly from these industry leaders about how their companies are preparing for the AI era—not in theory, but in practice.

For our team at Flow, a Korean startup often viewed as an “outsider” in the global SaaS landscape, being in the same room with unicorn- and decacorn-level companies was a wake-up call and a strong motivator. It reinforced our conviction that we must build a presence in San Francisco and Silicon Valley—the true arena of SaaS competition.

What stood out most was the sheer speed at which these companies are embracing AI-driven transformation. From OpenAI’s GTM leader Maggie Hott to Anthropic’s startup sales lead Kelly Loftus and Cursor AI’s Jacob Jackson (a former OpenAI researcher), the sessions were refreshingly candid. They shared not just strategies, but real-world trial-and-error stories—offering rare insight into how frontier AI firms are redefining sales, product development, and customer experience.

The defining theme of this year’s SaaStr Annual conference was clear: AI in SaaS is no longer a buzzword, it’s a business imperative.

While Korea continues to prioritize AI semiconductors and infrastructure, the focus at SaaStr was firmly on software. specifically, how SaaS companies are embedding AI to solve real customer problems. The discussion shifted from models like Claude, GPT, and Llama to their practical application in the field. The prevailing wisdom: "It's not the model that matters, but the outcome it delivers."

In earlier phases of AI adoption, companies emphasized that AI was embedded in their products. But the narrative has evolved. Kelly Loftus of Anthropic captured this shift succinctly: “Sell AI solutions, not AI features.” Her remark resonated deeply with attendees.

One of the most talked-about sessions centered on what Box CEO Aaron Levie called “Pragmatic AI”—a focus not on flashy tech demos, but on delivering tangible value to end users. This pragmatic lens has strong implications for Korean companies, many of which have historically emphasized real-world problem solving over technological showmanship. In the AI era, that mindset could be a competitive edge.

At Flow, we see this shift firsthand. In response to global trends, we are building AI agent capabilities to evolve from a domestic collaboration tool into a globally competitive platform. By unifying messaging, task management, community functions, and AI into one ecosystem, we aim to make teamwork more intuitive, efficient, and data-driven.

AI is transforming not only product features but internal operations. Companies like Box and Asana are using generative AI to streamline content creation, auto-generate marketing pages, and enhance development workflows—dramatically boosting productivity.

Sessions led by Christina (Partnerships at Linear) and Rob Gilio (Chief Customer Officer at Canva) highlighted that AI is not just a tool, but a catalyst for reinventing how work gets done.

Another major takeaway: ROI matters. Companies are under pressure to show that AI adoption leads to clear business outcomes, from cost savings to revenue growth. HubSpot CEO Yamini Rangan underscored this point with data: Since adopting AI, their clients have seen a 37% boost in marketing automation efficiency and a 22% reduction in sales cycle time.

Finally, investors emphasized the value of cultural intelligence. Richard Wong of Accel Partners noted, “The most successful SaaS companies combine technical excellence with deep cultural understanding.” For Korean firms expanding globally, this means technology alone isn’t enough, Localized insight and adaptability are equally critical.

Contrary to recent forecasts that the SaaS industry has entered a period of maturity, optimism dominated the floor at SaaStr 2025. The consensus: AI is breathing new life into SaaS and becoming its next major growth engine.

According to the 2025 Buyer Behavior Report presented by G2’s CMO Sydney Sloan and Research Director Tim Sanders, enterprise buyers remain concerned about the high fixed costs and fragmented tool ecosystem.

But speakers agreed: AI is solving these pain points, streamlining workflows, lowering switching costs, and restoring SaaS to a path of productivity-driven value.

One of the most compelling discussions centered around how AI is reshaping SaaS through bundling and unbundling. Jess Lee, partner at Sequoia Capital, noted that AI is accelerating the rise of “super apps” that consolidate messaging, project management, and collaboration. Yet paradoxically, it is also fueling demand for hyper-specialized, best-in-class tools, especially in niche domains.

“AI is doing both: driving platform consolidation and enabling domain-specific innovation,” she said. This duality signals a likely bifurcation of the market into a few large integrated platforms and many vertical-focused providers.

At Flow, this insight hits close to home. Our mission is to bundle key collaboration functions, messaging, task management, team community, into one unified platform. By eliminating the need for separate tools like Slack, Asana, Trello, or Notion, we aim to offer customers both cost-efficiency and productivity gains. With AI now woven into our roadmap, we believe our model is increasingly well-positioned for global relevance.

Another major trend: the rise of vertical SaaS—solutions deeply tailored to specific industries. Unlike general-purpose SaaS tools, vertical offerings in healthcare, legal tech, real estate, and financial services are leveraging AI to solve complex, domain-specific problems.

Peter Gassner, CEO of Veeva Systems and a pioneer in vertical SaaS, summed it up: “When AI is paired with deep industry knowledge, its impact is amplified tenfold.”

As horizontal players consolidate and vertical specialists gain ground, SaaS is entering a new era—fueled not just by innovation, but by strategic focus and domain depth.

Proposal for the Leap Forward of the Korean Software Industry

At SaaStr 2025, one thing stood out, not just what was present, but what was missing. Among thousands of attendees from around the world, Korean representation was virtually nonexistent.

This absence was striking, especially compared to Korea’s strong presence at consumer focused events like CES and MWC. It underscored a deeper concern: Korea’s software sector lacks global visibility and perhaps global ambition.

In the U.S., software companies dominate the upper tiers of market capitalization. In Korea, few software firms even make the list. The contrast reflects a systemic weakness in Korea’s software industry foundations.

SaaStr 2025 made it clear that software is no longer a backend tool. It’s the strategic core of every modern business.

As a16z partner David Ulevitch put it, “Every company is becoming a software company and AI is accelerating that shift.” For a country with global tech ambitions, Korea’s lag in the software race is a red flag.

The numbers highlight the gap. The U.S. SaaS market is valued in the hundreds of billions of dollars; Korea’s is in the low single digits—a difference of more than 40-fold. This disparity underscores a critical point: Korean SaaS firms can’t afford to think domestically. Global expansion isn’t optional. it’s existential.

Korean tech companies have historically thrived not by inventing foundational platforms, but by solving customer problems with speed and precision. Line, Coupang, Baemin, Yanolja, and Toss didn’t invent the smartphone OS—but they built services on top of it that transformed daily life. In the AI era, this customer-centric execution model could be a powerful advantage.

Rather than chasing core model development, Korea could focus on organizational culture reform, advanced work tools, and AI-driven services tailored to user needs. With this approach, Korean software can compete globally—and elevate the nation’s tech standing in the process.

Zoom CEO Eric Yuan offered a closing insight at the event:“Software begins with empathy, not technology.”

That mindset may be exactly what Korean firms need to internalize. Deep user empathy, combined with agile AI implementation, could be Korea’s unique edge in the global SaaS ecosystem.

As the AI wave reshapes the software world, now is the time for Korean companies to step forward. SaaStr 2026 should not be another missed opportunity. Korea’s software moment is here—if it chooses to seize it.

Lee Hak-jun is the founder and CEO of Madras Check, which developed the collaboration tool 'Flow'.

CEO Lee Hak-jun independently founded Madras Check, which started as an in-house venture of Webkesi. Recognizing the need for the enterprise collaboration tool market, it developed 'Flow' with a user-friendly interface and powerful features. Flow integrates various functions such as project management, messenger, OKR (objective and key result) setting, and video conferencing, and has grown rapidly in the domestic collaboration tool market. It has secured more than 5,000 paying corporate customers, including large corporations and public institutions such as Samsung Electronics, Hyundai Mobis, Mirae Asset Securities, and Gas Corporation. In 2023, the company launched the global version of 'MorningMate' and established local subsidiaries in the UK and Mexico.

On May 27, 2025, in celebration of its 10th anniversary, Madrascheck will launch 'Flow 4.0' and strengthen its position in the AI-based collaboration tool market.