Jason Dacaret

Executive Search & Japan Market Entry Advisory | Former CHRO & VC Operator | Co Founded Search Firm Acquired by Recruit Holdings

Tokyo, Japan

About

I have worked across executive search, operating leadership, and investment environments in Japan, Southeast Asia, and the United States for more than 25 years. What that experience ultimately provided was perspective across all sides of the leadership decision: running the search, making the hire as an operator, and participating in investment decisions as part of an investment committee. That combination shapes how I approach leadership hiring, organizational build, and market expansion work today. I began my career in Tokyo, co founding an executive search firm that I built over more than a decade before it was acquired by Recruit Holdings and integrated into RGF Executive Search. During that period, I led director to C suite searches primarily for U.S. based technology companies and multinationals building and scaling operations in Japan. Japan taught me early that many hiring problems are not actually hiring problems. More often, they stem from a mismatch between company stage, leadership expectations, operating realities, and what the market can realistically support. After Tokyo, I built and led RGF’s Southeast Asia business across Singapore, the Philippines, Thailand, Malaysia, Vietnam, and Indonesia with responsibility for regional growth, organizational build, and operational strategy across multiple markets. I have also held operating and investment roles similar to the executives and investors I work with today. As CHRO and Investment Committee Member at a Singapore based venture builder, I partnered with founders and boards on leadership hiring, organizational build, and investment evaluation across early stage technology companies throughout Asia. Later, as VP of People at a U.S. technology company during a high growth phase, I worked alongside the CEO and COO on leadership hiring and organizational scaling from inside the business itself. At SoftSource, I work with technology companies, venture capital firms, and senior operators on leadership and organizational decisions tied to Japan and APAC expansion. Most engagements begin before a search starts, usually around questions of market entry, leadership calibration, organizational structure, hiring sequence, and whether expectations are aligned with the realities of the market.

Experience

  • Parnter at SoftSource* K.K.
    Jan 2026 - Present · 7 mos

    I work with venture capital firms, technology companies, and senior operators on leadership and organizational decisions tied to Japan and APAC expansion. Most engagements begin before a search starts. The initial discussion is usually less about recruiting itself and more about how the business is entering the market, what stage the organization is actually in, how leadership authority is structured, and whether expectations are aligned with the realities of building in Japan. My perspective comes from operating across the investor, operator, and search sides of the market. I have been involved in investment evaluation, executive hiring, organizational build, and leadership assessment across venture backed and global technology environments. That combination shapes how I approach leadership situations, evaluate organizational risk, and engage with boards, founders, and management teams. SoftSource is a Tokyo based executive search and advisory firm supporting technology companies building, scaling, or recalibrating operations in Japan. We specialize in first market leadership hiring, from Country Manager placement through building the commercial, technical, and operational teams that follow. Over time, much of our work evolved beyond isolated executive search mandates into helping companies think more structurally about Japan expansion itself: leadership stage mismatch, operating model alignment, hiring sequence, HQ expectations, and the organizational realities that shape long term outcomes in the market. We work with venture backed and global technology companies across AI native platforms, cloud infrastructure, developer ecosystems, cybersecurity, fintech, and adjacent enterprise technology sectors. 2,000+ searches completed in Japan’s technology sector, including 100+ Country Manager placements since 2007.

  • Client Partner at Pedersen & Partners
    May 2025 - Dec 2025 · 8 mos

    Pedersen & Partners is a leading global Executive Search and Leadership Consulting firm, with 56 wholly owned offices in 50 countries across Europe, the Middle East, Africa, Asia & the Americas. Worked with startups, SaaS companies, and APAC based technology firms on retained leadership searches and organizational hiring initiatives across North America and Asia. Advised founders, investors, and executive teams on leadership hiring, market expansion, and organizational build during periods of growth, transition, and international scaling. Engagements included retained searches across AI, enterprise software, cloud infrastructure, and emerging technology sectors. Partnered with global clients on cross border hiring strategy, executive assessment, and GTM team build, while supporting broader leadership and organizational discussions tied to expansion and operating scale.

  • Director / Managing Member at The Austin Talent Group
    Apr 2020 - May 2025 · 5 yrs 2 mos

    Advised venture capital firms, portfolio companies, and technology startups on leadership hiring, organizational build, and go to market team expansion during periods of rapid growth and market transition. Led director to C level searches across AI, enterprise software, and emerging technology sectors, supporting founder led companies on leadership assessment, organizational scaling, and talent strategy tied to growth, financing, and M&A activity. Worked with founders and executive teams on building GTM capability, offshore hiring strategy, and international expansion initiatives, while incorporating AI driven market intelligence and assessment approaches into leadership search and advisory work.

  • Investor/Limited Partner at Eniac Ventures
    May 2010 - Dec 2024 · 14 yrs 8 mos

    Investor and Limited Partner in Eniac Ventures, an early stage venture capital firm focused on technology startups across software, infrastructure, AI, and emerging technology sectors.

  • VP, People at Thirstie
    May 2021 - Jul 2022 · 1 yr 3 mos

    Thirstie, a New York-based tech startup, connects brands with consumers. Its offerings include white-label e-commerce, consumer adoption, and data intelligence solutions for Beverage Alcohol brands. Thirstie helps brands power consumer interactions in an industry-compliant three-tier system. Thirstie received funding and a partnership agreement with industry leader RDNC, an $11.8B company. Cocktail Courier recently acquired Thirstie. Joined Thirstie during a period of rapid growth to build leadership and organizational capacity across the business. Partnered with the CEO and COO on executive hiring, organizational scaling, and talent strategy across GTM, engineering, legal, and corporate functions. Led leadership searches spanning C level, VP, and Director roles while supporting broader organizational planning and executive team development. Worked closely with management during a key stage of company growth, strategic partnership expansion, and operational scaling leading up to the company’s eventual acquisition by Cocktail Courier.