Guidance Counselor 2.0 With Dan DiGangi

​In this episode of Guidance Counselor 2.0, Taylor Desseyn talks with Dan DiGangi, Senior Engineering Manager at Postmark (ActiveCampaign), where he leads all things engineering — product, platform infrastructure, mail operations, security, and compliance — for a platform processing 3B+ emails a month.

​With 20+ years in software and 9+ as a people leader, Dan has built and scaled engineering teams across companies like DocuSign, Arrive Logistics, and OpenLane. The conversation covers what it actually takes to grow from individual contributor into engineering leadership, how to build diverse, high-performing teams, and why mentoring — and mental health in tech — matter as much as the technical work itself.

​For anyone eyeing the jump into engineering management, or already there and looking for perspective, this episode offers a grounded look at what leadership in tech really requires.