The CVC Head Who Negotiated: I Can Only Say No, and Every “No” Goes in a Spreadsheet

Chang Li’s path into Japanese insurtech started with a campus recruiting pitch she hadn’t planned on. A large domestic life insurer visited her college with a message about global expansion — Japan’s population is shrinking, the domestic market will shrink with it, and international growth is the answer — and it was interesting enough that she joined. She was lucky enough to land on the M&A team acquiring a US life insurer, then went to business school, where she took a part-time role at ShuFi, a Silicon Valley insurtech startup fielding interest from Japanese insurers.

That experience crystallized the problem she’s spent her career since trying to solve: a genuine gap between what global insurtech startups could offer and what Japanese insurers were actually equipped to absorb — different product maturity expectations, different security requirements, and a fundamental mismatch in decision-making speed between a startup that needs to move fast and a large corporation that treats every decision as carrying real risk.

In Episode 115 of InsurTechTalk, Chang and I covered how Japanese insurance CVCs evolved from powerless “listening posts” in Silicon Valley into some of the most active early-stage insurtech investors globally, why Japan still has no VC purely focused on insurtech, and what to expect from ITC Japan on March 12.

About Chang Li

Chang Li is VP of InsurTech and FinTech at Plug and Play Japan, based in Shibuya, Tokyo. Before joining Plug and Play, she worked at a major Japanese domestic life insurer on its US M&A team, and later worked part-time at ShuFi, a Silicon Valley insurtech startup, while in business school. Plug and Play Japan, which also has an Osaka office, runs venture investing and corporate acceleration programs connecting global startups with Japanese corporations, and now increasingly supports Japanese startups expanding abroad.

From Silicon Valley Tourists to Real Investors

The most substantive thread in the conversation traced how Japanese insurance CVCs transformed over roughly a decade, and it’s a genuinely useful case study in corporate innovation structure.

• Roughly eight or nine years before this recording, Japanese insurers began sending two or three people to Silicon Valley satellite offices to observe trends and report findings back to Tokyo
• Those early satellite teams had no decision-making authority — they were, in Chang’s description, essentially visitors who gathered information. When headquarters couldn’t move fast enough to act on what they found, and the satellite staff had no power to commit, the whole exercise struggled to produce real outcomes with startups that move at startup speed
• Over the following years, several insurers — MS&AD first, then Tokio Marine, Nippon Life, and Sumitomo Life — restructured their satellite operations to carry genuine, local decision-making authority

The specific story Chang told about MS&AD’s CVC founder (referred to as “Tak”) is the clearest illustration of how that authority got won. He negotiated a deal with headquarters: he would keep final investment approval with Tokyo, but under two conditions. First, headquarters had to respond within 24 hours, weekends and holidays included, because speed is existential in venture. Second, headquarters could only ever say no — never mandate a deal — but every rejection would be logged in a spreadsheet, permanently, so that if a declined startup later became “the next Google,” accountability for that decision was fully traceable.

Why the CVCs Now Beat Pure VCs at Insurtech Specifically

Chang’s broader argument is that this evolution has made corporate venture capital more effective than generalist VC specifically in insurtech, for structural reasons:

• Pure financial VCs struggle to understand insurtech’s operational dynamics without embedded domain experts — Tokio Marine, for instance, hired the original founder of Metro Mile onto its investment team specifically to bring authentic Silicon Valley insurtech pattern recognition back to Tokyo
• CVCs with real underwriting and industry expertise can conduct due diligence a generalist VC would need to outsource or rely on LPs for
• Beyond capital, CVCs like MS&AD and Tokio Marine now actively support portfolio companies expanding into Japan — Chang cited DA Life (from Europe) as an example where the CVC relationship has become genuinely hands-on in supporting the startup’s Japan market entry, not just a passive check

No Pure-Play Insurtech VC Exists in Japan — Yet

I asked directly whether Japan has a dedicated insurtech-focused VC comparable to what exists in the US market. The honest answer: no. A few generalist firms — Chang named Coral Capital, formerly 500 Startups Japan — have backed notable insurtech portfolio companies (JustInCase and Hokan, currently the two largest insurtech startups in Japan), but the investment thesis in each case is driven by the entrepreneur and company specifically, not a dedicated insurtech mandate.

Her explanation for why: Japan hasn’t yet produced a genuine pure-play insurtech IPO success story, which makes it harder for VCs to build conviction around committing to the category specifically. I pushed back gently on the framing — a strong acquisition by a larger insurer is just as much a liquidity success for early investors as an IPO — a point relevant to how the ecosystem’s maturity gets measured going forward.

Three “Global Cities,” Three Different Roles

Japan’s government-designated financial hub strategy — Tokyo, Osaka, and Fukuoka — assigns each city a genuinely distinct function rather than replicating the same pitch three times:

• Tokyo hosts the Financial Services Agency (FSA), which is why essentially every fintech and insurtech startup headquarters there — regulatory licensing and communication happen in Tokyo, and every major insurer’s headquarters is there as well
• Osaka leans more diversified — strong manufacturing base, major ports, and is positioning itself as a smart city ahead of Expo 2025, creating openings for embedded finance and embedded insurance tied to mobility and healthcare infrastructure
• Fukuoka is geographically distinctive — roughly a one-hour ferry from Korea, close to Taiwan and Southeast Asia — making it a natural low-cost entry point for founders and capital arriving from elsewhere in Asia. Chang noted Fukuoka’s local government offers some of the strongest founder-support policies of the three, plus a notably convenient airport (a 10-minute train from the city center)

Why Japan Innovates Slowly — And Why That’s Not Entirely Bad

Chang’s framing of Japan’s conservative pace of change was more nuanced than “bureaucratic resistance.” Her view: Japan has historically solved its problems so thoroughly that the resulting services — payments included — are already so mature and comfortable for end users that there’s genuinely limited incentive to disrupt them. Digital payment adoption lags many countries specifically because credit cards and existing payment rails already work extremely well for most people; a new solution has to already be highly mature to displace something customers are perfectly happy with, rather than succeeding on early-adopter enthusiasm the way it might elsewhere.

Her reframe: this reflects a highly mature society more than a resistant one — and it still leaves real openings for startups and corporations willing to solve genuinely unmet problems.

Government Support Is Real and Getting More International

Japan’s five-year startup promotion plan (launched roughly two years before this recording) includes tax and visa changes specifically aimed at making it easier for global entrepreneurs to establish businesses in Japan, plus free business-matching services for foreign founders. Chang cited Sakana AI — a generative AI startup founded in Japan by a former senior Google researcher — as a direct beneficiary of this push, and noted that the government has begun actively courting global-tier venture firms (she named Andreessen Horowitz and Sequoia among invited speakers at a major government-convened conference) specifically to bring outside risk-investment expertise into the domestic ecosystem, not just outside capital.

ITC Japan, March 12

Chang previewed the second edition of ITC Japan, run in partnership with the Financial Services Agency — the largest insurtech event in Japan and, by her account, genuinely global in its speaker roster.

• A full-day program with more than 25 sessions
• A main-stage discussion featuring the FSA’s head of insurance alongside a carrier and a startup representative, focused on activating Japan’s insurtech ecosystem and — notably — talent diversity, including specific efforts to bring more women and non-Japanese professionals into the industry
• Afternoon breakout tracks covering topics including LLM applications in insurance (featuring Hokan, one of Japan’s most well-funded insurtech startups) and embedded insurance, including a panel on what it would take to produce Japan’s first true insurtech unicorn

Her practical travel advice for international attendees: fly in the week before for Japan FinTech Week (March 5-8), when Sakura season is beginning in parts of the country, and — depending on timing — there’s still a window for skiing or snowboarding in Hokkaido or Niigata (roughly 90 minutes from Tokyo by Shinkansen).

Advice: Don’t Let the Evil Out

Asked for closing advice, Chang shared something her father told her that she says she’s never fully loved but has kept with her regardless: everyone carries some evil in their heart, and the discipline is simply never letting it out.

Key Takeaways

• Japanese insurance CVCs evolved from powerless information-gathering satellite offices into genuinely fast, locally-empowered investors — MS&AD’s negotiated 24-hour response requirement is a concrete example of how that authority was won structurally
• CVCs with embedded domain expertise (like Tokio Marine hiring Metro Mile’s founder) currently out-execute generalist VCs specifically in insurtech, where pattern recognition requires real industry fluency
• Japan has no dedicated pure-play insurtech VC yet, partly because the ecosystem lacks a landmark IPO success story to build category conviction around — though strong acquisitions arguably already provide that proof point
• Tokyo, Osaka, and Fukuoka serve genuinely distinct roles in Japan’s startup strategy rather than competing on identical positioning — regulatory access, smart-city infrastructure, and Asia-gateway geography respectively
• Japan’s slow pace of consumer-facing innovation reflects mature, already-excellent existing services more than institutional resistance — a nuance worth remembering before assuming market entry will be easy
• Government support has become genuinely international in ambition, actively recruiting global VC expertise (not just capital) to strengthen domestic risk-investment capability
• CVCs are increasingly doing double duty — investing in foreign insurtechs and then actively supporting those same companies’ expansion into the Japanese market, a hybrid capability pure VCs structurally can’t match