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Find your north star

Steve Winterfeld

CommunityHire Ground52 minBeginnerOpen on YouTube ↗

Where

Hire Ground
BSides Las Vegas

Duration

52 min

Offers career-planning guidance for cybersecurity professionals choosing between leadership, technical, and entrepreneurial paths.

Summary

Steve Winterfeld opens with his own path through the field, from military service and building a security operations center to compliance, banking and threat intelligence roles. A layoff pushed him to plan his career deliberately instead of taking whatever opportunity came next. He then walks through the kinds of roles newcomers can consider, including analyst, incident response, forensics, penetration testing and compliance work, and notes that the hours and stress differ widely between them.

The middle of the talk covers what keeps a professional growing. He recommends becoming a true expert in one area at a time, building partnership skills by learning how the business makes money and reading a company's financial filings, and developing leadership through managing projects, teams or volunteer groups. He also discusses learning habits, such as taking notes, teaching others and using deadlines or paid courses to force follow-through.

For the final stretch, he compares possible end-of-career targets: running a company, staying technical as a CTO, or leading security as a CISO, a role he says increasingly requires board-level communication. He closes with job-search advice: treat the search as full-time work, measure resumes by accomplishments, practice interviewing, and build a support network, since most people find jobs through contacts.

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