Peter Sobiloff spent nearly three decades as a software company CEO before joining Insight Partners, where his first investment deal went from funding to a $150 million sale in just five months, helping prove that hands-on operating expertise could be a key differentiator for venture firms. He focuses on specialized B2B software in regulated industries like legal and healthcare, often staying close to founders for years before investing, as he did with Medidata, which Insight backed at a $30 million valuation and later sold for around $6 billion. Peter Sobiloff spent nearly three decades as a software company CEO before joining Insight Partners, where his first investment deal went from funding to a $150 million sale in just five months, helping prove that hands-on operating expertise could be a key differentiator for venture firms. He focuses on specialized B2B software in regulated industries like legal and healthcare, often staying close to founders for years before investing, as he did with Medidata, which Insight backed at a $30 million valuation and later sold for around $6 billion.