Senior Systems Administrator

ABOUT US We are fixing US healthcare by building an AI-native physical care platform, starting with home health. Home health is a $140B industry with less than $10B in EBITDA — 40% of revenue is spent on pure administrative waste. We automate this work with AI, creating a fundamentally different cost structure compared to incumbents. This lets us rapidly take market share by serving the 30% of patients who go untreated today. By reshaping the cost structure of this industry, we unlock its growth. We’ve built one of the best AI teams in the world (from Character AI, Scale, Palantir, Citadel, Jane Street) and paired them with a team of healthcare veterans and ex-MBB strategists to build a new type of healthcare company: one that delivers care at the speed of an AI company. Our physical care platform already operates with 30pp higher gross margins than traditional home health providers. With our AI advantage, we pay nurses more, remove their admin burden, and unlock the scale economics that have been missing from this fragmented industry. If we served this entire $140B market, instead of $10B in EBITDA, we’d drive $60B. We're starting with home health, then expanding to all delivered care. Our mission is “any care, any where”. Fundamentally, our incentives are aligned with America. Every dollar in revenue we make is two dollars taken out of the healthcare system. If we succeed, so does US healthcare. THE OPPORTUNITY - SYSTEMS INFRASTRUCTURE We're scaling from 500 to 2,500 employees over the next year while integrating multiple acquired entities. Our IT infrastructure needs to match the speed of an AI company—not the bureaucracy of traditional healthcare. We're insourcing IT operations and building a unified, secure platform across all business units. This means consolidating fragmented systems, hardening security and compliance, and creating the infrastructure that lets our clinical and AI teams move fast without breaking things. Think of it as a blend of: • Defensive design (prevent attacks at every layer, but also prepare for breaches, minimize blast radius, and detect incidents fast) • Greenfield architecture (you'll have latitude to design best-in-class infrastructure, not patch legacy systems) • Frictionless operations security (tight access control with low friction — make the secure path the easy path) You'll be one of the earliest members of our internal IT team, working directly with leadership, engineering, and operations to build the infrastructure foundation that powers care delivery across the USA. This role is designed for you if you have a low ego, love solving problems that matter, and are ready to build infrastructure for an industry-changing company. WHAT YOU'LL DO You'll own and drive high-impact, ambiguous problems end-to-end, such as: 1. OWN SECURITY POSTURE ACROSS ALL SYSTEMS • Implement and enforce cybersecurity controls: MFA, conditional access, EDR, vulnerability scanning, and secure remote access • Lead incident response and coordinate with our security partners • Maintain HIPAA-aligned technical safeguards and support CMS and state audits • Build and maintain security documentation, policies, and system diagrams—we cannot secure what we cannot see 2. ARCHITECT AND MAINTAIN CLOUD INFRASTRUCTURE • Deploy and maintain Microsoft 365, Entra ID, Intune, VPNs, and virtual desktop environments • Manage backups, disaster recovery, monitoring, and patch management • Lead system upgrades, migrations, and integrations as we consolidate business units 3. DRIVE M&A SYSTEM INTEGRATION • Lead post-acquisition integration: directory consolidation, email migrations, endpoint standardization, network integration, legacy decommissioning • Participate in IT due diligence for acquisitions—system inventories, security posture assessments, risk identification • Develop repeatable IT integration playbooks to support our ongoing acquisition strategy 4. MANAGE ENDPOINTS ACROSS A DISTRIBUTED WORKFORCE • Secure Windows, macOS, and mobile devices using MDM platforms (Intune, Jamf, Knox) • Standardize device configurations, encryption, and compliance policies • Own asset tracking and lifecycle management for field and corporate staff 5. PARTNER WITH OPERATIONS TO ENABLE FAST, SECURE GROWTH • Support and administer business-critical platforms: HRIS/Payroll (ADP, Rippling), EHR/EMR (Homecare Homebase), compliance systems (Relias) • Partner with HR on secure onboarding/offboarding—our target is same-day provisioning and immediate access revocation • Provide escalation support for complex issues impacting remote and field-based staff WHO YOU ARE We're looking for high-ceiling, low-ego builders. This is a startup, and every day brings its own adventure. If you bias to action and want early ownership, this is the place for you. MUST-HAVE EXPERIENCE • 7+ years of enterprise systems administration experience • Demonstrated experience in HIPAA-regulated or highly compliant environments • Strong hands-on experience with Microsoft 365, Entra ID, and Intune • Experience with macOS administration, iOS device management, and cross-platform environments • Proven ability to manage VPNs, firewalls, network security, and backup/disaster recovery systems • Excellent documentation, troubleshooting, and communication skills HOW YOU WORK • Owner mindset: you'd rather be accountable for results than wait for someone else to fix the problem • Bias to action: you hate bureaucracy and want to move fast • Security-first thinking: you prioritize prevention, but also assume breach and design for containment, not just prevention • Clear communicator: you can go from a messy problem to crisp documentation • Comfort with ambiguity: you don't need a perfect brief; you can help create it • Low ego: this is a startup, you want to get scrappy NICE-TO-HAVES • Healthcare, or multi-site clinical operations experience • M&A systems integration experience—you've migrated or consolidated IT environments post-acquisition • Jamf and Apple Business Manager administration • Knox, or other Enterprise Device Management for tablet/mobile devices • Virtual desktop infrastructure (VDI) experience • Certifications: Microsoft (Azure/M365), CompTIA Security+, Jamf, CISSP WORKING CONDITIONS • Fully remote role with reliable high-speed internet required. • Occasional travel to branch offices or data centers may be required for major deployments or audits. • On-call or after-hours work may be required during outages or critical system changes. WHAT WE OFFER - Opportunity for growth in a fast-growing company - Collaborative team valuing innovation and problem-solving - Competitive salary and equity compensation - Flexible time off policy—we expect most employees to take at least 3 weeks of vacation per year - 401(k) retirement plan with employer contribution - Comprehensive health insurance, dental, and commuter benefits