or apply directly on Pilot.com's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 5 days Pilot.com's roles stay open a median of 35 days
- Reposted
- No
- Salary listed
- Yes 100% of Pilot.com's roles list one
- Ghost-job risk at Pilot.com
- moderate 4 stale, 0 reposted of 13 open
- Hiring momentum
- 15 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from Pilot.com's own greenhouse board since 2026-08-03. Full hiring picture for Pilot.com.
About this role
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
- 3/5
- freshness
- 5/5
- career value
- 4/5
- role clarity
- 4/5
- pay transparency
- 5/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Pilot.com as an employer.
What you need
- 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 you get
- 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
Worth weighing
- 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
Summarised from Pilot.com's posting. Read the full original.
Listed by Pilot.com on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
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