Chuck Strahlendorff chased one decision-maker at UnitedHealth for two years. Roughly a hundred emails. At least fifty calls. Bagels dropped off for the man’s staff. Not one reply. Then his phone rang with a 317 area code, and it became the largest deal of his career.

Scott and Billy sit down with Chuck, who leads healthcare sales at ServiceNow after 30 years in tech, for a conversation about the human element of doing business and why most reps quit three touches too early.

Inside this episode:

The trap that ends sales careers: giving up way too soon

Day one at a struggling software company, and the question that blindsided him (“what programs can we put in place so we can make payroll next quarter?”)

The weekly point-of-view email that builds an outbound brand, and the CIO who called it a newsletter

Why he still shows up unannounced with handwritten notes in the age of AI

Do the grunt work: getting water, taking notes, being the last one to turn out the lights

Should you stay in one industry or try several? His answer changed his whole career

What he tells his own kids about fighting for a job when everyone has a perfect AI-written resume