Robert Ross

Robert Ross

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Investor at Cluster Capital
San Francisco, California, United States

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work
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  • Hustle Fund
    Investor
    Hustle Fund
    Jan 2023 - Current (3 years 4 months)
    Early stage VC & Angel Squad investor community. Hustle invested in Webflow, NerdWallet & many more.
  • The GenAI Collective
    Organizer
    The GenAI Collective
    Jan 2023 - Current (3 years 4 months)
    The world’s largest AI community. We are a global non-profit uniting 40,000+ pioneers – founders, researchers, operators, and investors – exploring the frontier of AI in major tech hubs worldwide. Through events, workshops, and community-led research, we empower the AI ecosystem to collaboratively steer AI’s future toward trust, openness, and human flourishing.
  • Dreamable Inc
    Founder/CEO
    Dreamable Inc
    Jan 2023 - Current (3 years 4 months)
    I lead a team designing and building AI agents for emerging fund managers and early-stage startups. Our agents integrate directly into your workflows — supporting LP raise, sourcing, diligence, founder coaching, internal ops, and portfolio reporting for VCs, and supporting GTM, operations and executive management for startups. Each engagement is custom — tuned to your goals, tools, and tempo.
  • YC Startup School Alumni
    Founder
    YC Startup School Alumni
    Jan 2022 - Current (4 years 4 months)
    Founder of the largest community of YC Startup School Alumni https://www.linkedin.com/groups/12682370/
  • AngelList
    Investor
    AngelList
    Jan 2020 - Current (6 years 4 months)
  • Cluster Capital
    Investor
    Cluster Capital
    Jan 2017 - Current (9 years 4 months)
  • Microsoft
    Vice President Business Development
    Microsoft
    Jan 2016 - Dec 2017 (2 years)
    After Xamarin's acquisition by Microsoft, I led partnerships for mobile developer and devops solutions, and helped guide our integration.
  • Xamarin acquired by Microsoft
    Vice President Business Development
    Xamarin acquired by Microsoft
    Jan 2013 - Dec 2016 (4 years)
    Xamarin was a cross-platform framework to develop iOS & Android apps. We grew to $48M ARR & 1.4M+ devs. Raised $82M & acq by Microsoft. I was deal lead on partnerships with Microsoft, AWS, Google, Salesforce, IBM, Oracle, SAP, & Samsung. My 10-person team led thousands of partner integrations across security, analytics, payments and more. I also led buy vs build due diligence on acquisitions. Investors: Lead Edge, CRV, Ignition, Insight, Floodgate.
  • WishPop
    Founder/CEO
    WishPop
    Jan 2011 - Dec 2013 (3 years)
    Founded consumer app & served as chief product officer. WishPop let kids create a curated wishlist and thank you cards for parent-approved family & friends who got reminders to buy the right gift for for the right kid at the right time. Top rated in iOS app store. I shut down WishPop when I joined Xamarin.
  • Gild acquired by Citadel
    VP Marketing & Business Development
    Gild acquired by Citadel
    Jan 2010 - Dec 2012 (3 years)
    Gild was an AI SaaS that rated developer code and skills on GitHub and StackOverflow. I signed dozens of customers and led mobile product management. Gild was acquired by Citadel. Investors: Menlo, Correlation, Globespan, Baseline, Sapphire, Drive, DNX, TMT.
  • Cryptography Research Inc acquired by Rambus
    VP Business Development
    Cryptography Research Inc acquired by Rambus
    Jan 2006 - Dec 2009 (4 years)
    CRI was founded by Paul Kocher, co-inventor of SSL. I led BD for our digital media security business, adopted by Apple, Samsung, Sony, Fox, Disney & others. CRI was acquired by Rambus for $342M.
  • Zero G Software acquired by Macrovision now Flexera
    VP Sales & Business Development
    Zero G Software acquired by Macrovision now Flexera
    Jan 2003 - Dec 2006 (4 years)
    Zero G provided software deployment and devops solutions. I led sales & BD, building a base of thousands of enterprise customers including Apple, AT&T, Microsoft, HP, SAP, Oracle, CA. Zero G was acquired by Macrovision (now Tivo).
  • Adero acquired by Colt
    VP Business Development
    Adero acquired by Colt
    Jan 1999 - Dec 2002 (4 years)
    Adero was a content delivery network (like Cloudflare & Akamai). I built our strategic partnerships, and was deal lead on our $80M Series C. Investors: Microsoft, Intel, Reuters, Mitsubishi, Yahoo, Fidelity, Spectrum Equity & MC Partners. Adero was acquired by Colt, a cloud infrastructure provider.
  • ValiCert IPO acquired by Axway
    VP Business Development
    ValiCert IPO acquired by Axway
    Jan 1997 - Dec 1999 (3 years)
    ValiCert provided digital security solutions. I built relationships with BofA, Barclays, Deutsche Bank, British Telecom, France Telecom, Deutsche Telekom & others. Investors: August, Bessemer, DFJ, USVP, Intel, France Telecom, Gemplus (now Thales) & Thomson. IPO & acquired by Axway, a cloud infrastructure provider.
  • Individual Inc acquired by Thomson Reuters
    Director Business Development
    Individual Inc acquired by Thomson Reuters
    Jan 1991 - Dec 1997 (7 years)
    INDIVIDUAL provided competitive intelligence services. I signed enterprise license deals with our largest customers including AT&T, Cisco, DirecTV and built a $2.4M deal with Microsoft, helping our ARR grow from $1M to $30M. After our IPO, Thomson Reuters acquired INDIVIDUAL. Our IPO S1 filing: http://goo.gl/UYtASy
  • Apple
    Systems Engineer
    Apple
    Jan 1989 - Dec 1991 (3 years)
    I developed custom solutions for several campus-wide implementations for Apple education customers, including Dartmouth, Harvard Business School, and Boston area K-12 school districts.
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  • Y Combinator
    Startup School S22
    Y Combinator
  • Choate Rosemary Hall
    High School Degree
    Choate Rosemary Hall
    Choate opened my eyes through inspiring teachers Johannes van Straalen, a Holocaust survivor who shared his first-hand accounts, and the extraordinary Señor Juan López, who led me on 2 semesters in Spain and reading Don Quixote in Spanish.
  • Duke University
    BA, Coursework: Computer Science, Political Science & Religion
    Duke University
    I spent a semester in Israel with the Duke Archeology Program. We excavated the "Mona Lisa of the Galilee", a beautiful 3rd century mosaic preserved in the rubble by an earthquake.