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← Pilot.com

IT Systems Lead

Pilot.com
Location
San Francisco, California
Posted
9 days ago
Department
Information Technology
Salary
$115,000 - $156,000
What they actually want (must-haves)
  • 5+ years in IT, with at least 2 as a lead or sole admin at a SaaS or similar technology company
  • Deep hands-on Okta experience, including Workflows and complex Authentication flows
  • Experience managing Macs with an MDM and working knowledge of Windows
  • Comfortable owning AV, conference rooms, and events end to end
  • Familiar with SOC 2 and ISO27001 controls
  • Personable, patient, and methodical approach to problem-solving
Nice to have
  • Direct experience with InfoSec related initiatives such as SOC2, ISO27001, NIST, FedRAMP
  • Hands-on experience deploying AI agents for IT or Operational workflows
  • GitHub Enterprise, developer tooling administration, Cloud IAM experience
  • Prior fintech or regulated-industry experience
  • Relevant certifications (Okta, Jamf/Kandji, Network+/Security+)
What the job really is

As the IT Systems Lead at Pilot, you will manage day-to-day IT operations for the San Francisco office, supporting a hybrid workforce. Your responsibilities include administering systems like Okta and Google Workspace, managing hardware and access requests, and providing helpdesk support. You will also play a key role in developing the InfoSec program and supporting AI tools to enhance operational efficiency.

Benefits
  • Flexible vacation/time-off policy
  • All federal holidays are observed
  • Competitive benefits package including additional wellness benefits
  • Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
  • 401(k) plan
  • Equity eligibility for full-time regular positions
Things to weigh
  • Full-time in-office role, which may not suit all candidates
  • Role involves hands-on IT support, which may be demanding
  • No mention of remote work options for this position
  • AI-assisted operations are a growing focus, which may require adaptability
Job score4.2/5
Benefits3/5
Freshness5/5
Career value4/5
Role clarity4/5
Pay transparency5/5

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