const regex = new RegExp('(?<=[a-z\\d])([A-Z$][A-Za-z]*(?: +\\S+?)*):', 'gm')
const 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']]]
`;
const subst = `, \1:`;
// The substituted value will be contained in the result variable
const result = str.replace(regex, subst);
console.log('Substitution result: ', 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 JavaScript, please visit: https://developer.mozilla.org/en/docs/Web/JavaScript/Guide/Regular_Expressions