RC

Rob Chaplinsky

Investor | Venture Capital | Entrepreneur

Incline Village, Nevada

Overview 

Rob Chaplinsky is a seasoned investor, venture capitalist, and entrepreneur currently serving as the Managing Director at Link Ventures. With a strong background in mobile technology and business strategy, he has held key roles at various companies including Bridgescale Partners and Xactly Corp, and serves as a board member, investor, and advisor for multiple startups, showcasing his expertise in venture financing and strategic partnerships. Chaplinsky's career highlights include his role as Managing Director at Link Ventures, where he leads investments and provides strategic guidance, and his involvement in advising and mentoring startups like Axonify and BlueCat, demonstrating his commitment to fostering growth and innovation in the entrepreneurial ecosystem.

Work Experience 

  • Managing Director

    2018 - Current

    Link Ventures invests in early stage business that leverage AI, ML and data science.

Early stage VC investing in startups leveraging data science, machine learning and AI technologies.

  • Board Member, Investor

    2020

  • Board Member, Investor

    2020 - 2024

Trust & Will is the leading digital estate planning and probate platform.

Raised $48,000,000.00 from Sahin Boydas, AARP and Halogen Ventures.

  • Seed Investor

    2017 - 2021

Loop is a return portal that automated all the returns and refunds of products.

Raised $125,450,000.00 from Harmony Partners, Renegade Partners, Peterson Ventures, Ridge Ventures, CRV, Lerer Hippeau, Shopify and FirstMark.

  • Investor

    2017 - 2020

  • Managing Director

    2005 - 2018

    Bridgescale is a multi-stage venture capital firm that invests in a broad sprectrum of information technology sectors. The key principals bring decades of investment and operations expertise, a vast network of Silicon Valley relationships, and a deep understanding of the high-growth technology sector. As Co-founder and Managing Director. Notable recent exits include the IPO of SaaS security company Proofpoint, the IPO of SaaS work force compensation company Xactly, the sale of IOT company Jasper to Cisco, the sale of performance HRM SaaS company Rypple to Salesforce.com, and the sale of SaaS workforce management Dayforce to Ceridian.

  • Investor, Advisor

    2010 - 2017

    Leading SaaS performance compensation software company serving thousands of customers.

  • Investor | Advisor | Startup Coach | Mentor | Board member | Chairman

    2012 - 2016

    Axonify is the world’s first Employee Knowledge Platform. Pushing beyond the boundaries of corporate eLearning, it combines an award-winning approach to micro-learning, with innovative knowledge-on-demand capabilities to ensure employees do the right things right. The entire experience is gamified, driving high levels of participation and can measure employee knowledge growth, tying it directly to behavior that powers business performance. Axonify has several fortune 100 customers is growing over 100% per year. I was the first investor in the company when it was called 17muscles and helped the management team scale the company into one of Waterloo's biggest software success stories. I resigned from the board after a private equity firm bought out my position in the company.

  • Investor | startup coach | advisor | mentor | stategic advisor | Board Member

    2009 - 2016

    BlueCat is a leading network security technology provider that enables customers to build and manage their most complex network infrastructure to meet the rapid pace of change of their business. The company is a global leader in their segment and customers include a good portion of the Fortune 100 enterprises. I invested in this company in 2009 and resigned from the board after i sold my equity position in the company to a private equity firm.

  • Advisor

    2014 - 2016

    Biolinq is pioneering computational biology technology and micro on-body biosensors for consumer and medical applications.

Biolinq develops a wearable biosensor platform that is capable of measuring blood level information.

Raised $254,251,237.00 from Niterra Ventures, Taisho Pharmaceutical Holdings, Features Capital, Aphelion Capital, Alpha Wave Ventures, Global Health Investment Corporation, Senvest Management, AXA Investment Managers, Pegasus Tech Ventures and RiverVest.

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