re = /(?<=[a-z\d])([A-Z$][A-Za-z]*(?: +\S+?)*):/m
str = '[[\'Company OverviewCompany: HowSector: SoftwareYear Founded: 2010One Sentence Pitch: Easily give and request low-quality feedback with your team to achieve more togetherUniversity Affiliation(s): Duke$ Raised: $240,000Investors: Friends & familyTraction to Date: 10% of monthly active users (MAU) are also active weekly\'], [[\'Company OverviewCompany: GrubSector: SoftwareYear Founded: 2018One Sentence Pitch: Find food you likeUniversity Affiliation(s): Stanford$ Raised: $340,000Investors: Friends & familyTraction to Date: 40% of monthly active users (MAU) are also active weekly\']]]
'
subst = ', \\1:'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html