Senior IT Support Engineer

About the role

You'll join Parachute Health's IT & Security team, working alongside engineers and analysts who keep our healthcare technology environment secure, compliant, and operationally efficient. You'll gain hands-on exposure to identity, endpoint, network, and cloud security, compliance, and incident response in an environment governed by SOC 1, SOC 2, and HITRUST CSF.

Responsibilities

• IT operations & endpoint
• Support day-to-day IT operations: user onboarding/off-boarding, hardware provisioning, troubleshooting tickets, and end-user support.
• Help manage our macOS laptop fleet, MDM enrollment, configuration, software deployment, and compliance baselines.
• Troubleshoot connectivity, hardware, software, and authentication issues across Mac, Linux, and Windows environments.
• Document fixes, runbooks, and FAQs to help the team scale.
• Identity & access
• Aid with Okta administration, user lifecycle, group management, SSO/MFA configuration, application assignments, and access reviews.
• Help run periodic access reviews and collect audit evidence.
• Network & security tooling
• Support ZScaler operations, policy review, bypass requests, log analysis, and user troubleshooting.
• Help maintain DLP policies and triage alerts for potential data exfiltration.
• Aid with WAF rule review, false-positive tuning, and traffic analysis (AWS WAFv2 / Akamai).
• Sustain SIEM operations in Splunk/Wazuh by querying logs, building dashboards, and tuning alerts.
• Scripting & automation
• Write and maintain scripts to automate repetitive IT/Security tasks - log analysis, evidence collection, ticket enrichment, account hygiene, and reporting.
• Build small tools that make the team faster (no full-stack development required).
• Contribute to and use AI/agentic workflows the team has built (MCP servers, Claude-based runbooks) to accelerate investigations.

Requirements

• Bachelor's Degree in Cybersecurity, Information Technology, Computer Science, Information Assurance, IT Management, or a related field.
• Scripting experience is required. You can write working scripts in at least one of: Bash, Python, or PowerShell. You don't need to be a software developer, but you should be comfortable automating tasks with code.
• Working knowledge of the Linux command line, file system navigation, permissions, process management, log inspection (grep, awk, sed, tail, journalctl).
• Comfort with macOS as a daily-driver OS and basic troubleshooting on Mac.
• Solid IT troubleshooting fundamentals, networking basics (DNS, DHCP, VPN, TLS), authentication flows (SAML, OAuth, MFA), and hardware/software support.
• Comfort using Git, GitHub, and the terminal.
• Actively follows trends in IT, cybersecurity, and AI, with a strong desire to experiment with new tools.
• Strong written communication; you can document what you did so others can use it.
• Must reside in the U.S.

Nice to have

• Hands-on exposure to any of: Okta, ZScaler, Jamf/Kandji/Intune, CrowdStrike/SentinelOne, Splunk, Wazuh, AWS, GCP - academic labs, home labs, and personal projects all count.
• Familiarity with DLP concepts (data classification, exfiltration channels, false positives).
• Familiarity with WAF concepts (OWASP Top 10, rule tuning, rate limiting).
• Experience with SIEM querying (Splunk SPL, Wazuh rules, Sigma) or log analysis.
• Exposure to compliance frameworks (SOC 2, HIPAA, NIST CSF, ISO 27001).
• Experience with LLMs, agents, MCP servers, or prompt engineering through projects, hackathons, or coursework.
• SQL skills for querying data (Postgres, Redshift, BigQuery).
• Participation in CTFs, TryHackMe, HackTheBox, or similar.
• A public GitHub portfolio with scripts, automations, or write-ups.
• Interest in healthcare technology or working in a regulated environment.

Benefits

• Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums.
• Employer HSA Contribution: Company-funded contributions to your Health Savings Account.
• 401(k) Retirement Plan
• Equity Incentive Plan
• Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance.
• Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces.
• Flexible Vacation Policy
• Summer Fridays: 5 additional Fridays off during the summer (separate from PTO).
• Home Office and Wellness Stipend
• Monthly Internet Stipend
• Annual Learning and Development Stipend

Pay

Base Salary Band (based on experience and level): $60,000 - $105,000

Schedule

Full-time