Chris Aylott

Background

Chris spent the early part of the 2010s managing email infrastructure for a string of early-stage SaaS businesses — configuring sending domains, monitoring IP reputation, keeping warmup on track, and making sure product emails actually arrived. The work was unglamorous but critical: email was the backbone of every go-to-market motion, from onboarding to cold outreach to transactional delivery.

The tools available at the time shared the same fundamental problem: they all tested deliverability against synthetic seed networks — pools of vendor-controlled inboxes that accepted everything. Sender scores looked fine. But real users on Gmail, Outlook, and Yahoo were sending emails straight to spam. The dashboards reported green. The open rates told a different story.

In 2019, Chris built the first version of InboxPlease around a single principle: if you want to know where email lands, test it against real inboxes with real filtering. The product has been in active development since, adding AI-powered warmup, blacklist monitoring, and sender reputation tools — all built on the same foundation of honest, real-world testing.