Enterprise to startup, a security career field report

So you've joined a startup that's smaller than the security team at the enterprise you spent years building your security knowledge and career? You're discovering that much of what made you effective was the entire organization around you.

This session is a field report on making that move: from an 85,000-person enterprise (and shrinking) to a 150-person growth-stage startup.

Low-friction ways to improve security posture right away, methods for identifying gaps in need of immediate attention vs. those that can wait, and how to start building durable security hygiene at a critical point in your new company's history.

Transcript

1. Enterprise to Startup Tony Rice Cloud Security Engineer October 2026 A Security Career Field Report
2. Hats I’ve Worn Telecom GovtSvcs enterprise small startup Telecom BioTech enterprise growing startup
3. Environment Scale Early Stage • Focused output Focused security needs • lean canvas • Agile/Scrum Enterprise to Startup Mid-Market/Scaleup • Increased complexity more partners • quarterly OKRs • SAFe Enterprise • Massive scale • Established teams • Fewer partners more DIY • Strategic planning • OGSM / pillars 3 Courtesy FoMoco / Boston Dynamics / LucasFilm
4. Why Make the Leap? Enterprise to Startup Take Inventory 4 Enterprise to Startup
5. Good news! This guy doesn’t work there Enterprise to Startup 5 Images courtesy Judgmental Films / Cubicle Inc.
6. Same problems, different environments Large enterprises Smaller startups Security organization Smaller teams with broader Specialized large teams with specific responsibilities responsibilities and less specialization Decision-making Multiple stakeholders provide oversight and coordinated decisions Fewer decision-makers and more direct ownership Budget More resources, shifting priorities, abrupt changes Tighter budgets, careful prioritization and resource allocation Security tooling Established platforms and mature toolsets Selective use of tools, services, and external partners Governance Established risk management, compliance, and formal audit processes Governance practices scaled to the organization’s size, maturity, and regulatory needs More policy, fewer relationships Closer to the people building and operating systems Engineering relationships Enterprise to Startup 6
7. … but these guys do … and now you need them Enterprise to Startup 7 Images courtesy Judgmental Films / Cubicle Inc.
8. Evolving problems, different scales Measured across 250 InfoSec job postings for remote or Raleigh-Durham area onsite roles Enterprise to Startup 8
9. Security without an army Enterprise to Startup 9
10. Security without an army Enterprise to Startup 10
11. LEARN 30-60-90 plan Enterprise to Startup 11
12. Understand your security vendors Enterprise to Startup 12
13. VALIDATE 30-60-90 plan Enterprise to Startup 13
14. BUILD CREDIBILTY 30-60-90plan Enterprise to Startup 14
15. Questions?