Cracking Into a Healthcare System Through the Help Desk

The Challenge

I had been trying to reach the CISO of a major health system for three months with no success. Emails bounced off an assistant, calls went to voicemail, and LinkedIn messages went unread. The account was worth pursuing — 15 hospitals, 20,000 employees, and a known password reset problem — but the front door was locked.

The Approach

I shifted my approach and called the IT help desk manager instead. Help desk managers live in the pain of password resets every day — they are not gatekeepers, they are champions waiting to be found. The help desk manager told me they were handling over 800 password reset tickets per month at an average cost of $25 per ticket. That was $240K per year in help desk cost alone.

I helped the help desk manager build an internal business case showing the cost of password resets, the time clinicians lost to authentication issues, and the security risks of password-based workflows. He presented it to the CISO with our ROI calculator attached. The CISO called me the next day.

The Result

The help desk manager became our internal champion. The CISO approved a $350K pilot for passwordless authentication across three hospitals, with a planned expansion to all 15 facilities. The deal closed in 90 days because the business case had already been built and validated internally before I ever spoke with the CISO.

Key Takeaway

When the C-suite door is locked, find someone who lives in the pain every day and help them become your champion. Bottom-up selling works because it transforms an inside sales pitch into an internal initiative that the executive team feels ownership over.