Outlook Startups

Cirrus Insights is a productivity platform for Gmail and Outlook that helps sales teams with prospecting, email tracking, meeting scheduling, and deal closing. Over six years, Brandon Bruce grew the company from a few hundred thousand to over $1M MRR with 150,000 paying users and 250,000 total users across acquired products. The company maintains a bootstrapped model with low churn (~15-20% annually) and healthy unit economics, recently acquiring Attach to expand document management and e-signature capabilities.

Showpad is an enterprise sales enablement platform founded in 2011 by PJ Broughton that helps marketing and sales teams manage content and deliver branded buyer experiences. Starting from a mobile-first approach to solve a client's trade show problem, Showpad grew to 1,000 paying customers across 50 countries with an average contract value of $30,000, reaching $30M ARR with 70% YoY growth and 130% net revenue retention.