Jonathan R.

Background

About Jonathan R.

I’ve built a career by becoming the person no one saw coming – not just supporting the business, but becoming it. I embed in Legal, HR, Healthcare, Finance, Anywhere – doesn't matter – absorb systems, logic, processes, and vendors faster than the experts inside. then automate the pain, scale the platforms, and stabilize what others avoid. I don’t specialize in one domain – I run the operational nervous system: Identity & Access: Okta, SailPoint, RBAC, SCIM, SAML, OAUTH, low-code workflows, Jenkins Enterprise Systems: AD, DNS, DHCP, PKI, RDS, DFS, GPO, PowerShell, Microsoft 365 (Exchange, productivity, Copilot, Entra), Mimecast. Server lifecycle & hardening, legacy + modern coexistence. Tanium for config, remediation, risk, asset visibility, patching, telemetry SaaS Ops: Torii, usage visibility, spend management Endpoint Management: Intune, SCCM, Jamf, macOS/mobile, VDI Legal: IT architecture for eDiscovery, vendor reviews, compliance, case management, 3rd party risk HR: IT advisor for Workday, Greenhouse, Kronos, and other HR systems – driving integrations across platforms Service Delivery: Tier leadership, escalation, coaching At Chewy, I didn’t just lead platforms – I built the teams behind them. I created Endpoint Engineering & HRIT from scratch, and helped shape IAM from the ground up. Chewy grew from 7K to 22K+ employees, 45+ sites, 3 countries – and I’ve been at the center of that evolution the entire way. I shaped Chewy’s Okta platform into one of the most mature in the space – scaling from 43 to 900+ apps, leading our OIE migration, influencing product direction, and putting us in the top 3% of Enterprise customers for passwordless auth. I brought the same depth to Torii – advising roadmap strategy, presenting at internal summits, and inspiring feature launches. I’ve built systems supporting 22K+ users, B2B identities, 12K+ devices, and 2,200+ SaaS apps – automated, and delivered at scale. I’ve saved $25M/year through SaaS rationalization and automation, eliminated 5k+ hrs/mo of manual work, and delivered zero-touch onboarding. 🧠 My philosophy is simple: systems should enable people, not burden them. I balance experience, security, and manageability like a three-legged stool. My leadership is direct, protective, and empowering. I give teams air cover and clarity to move fast – without breaking things, burning out, or getting buried in noise. Strategic versatility. Executive range. Systems leadership. Adaptive intelligence. This isn’t a headline. It’s the job I already do – and the value I bring.