System Engineer Manager

As a leader in Medicare health insurance distribution, Spring Venture Group guides people through one of their most important life decisions - finding the right insurance coverage. We are on a mission to be the most trusted partner for our customers and our people, enabling empowered decisions along the journey to health and financial well-being.

Spring Venture Group offers incredible culture, benefits, and fantastic income potential in a stable and successful work environment at a Medicare agency. This starts with a workplace that empowers people to do their best work. Come build a rewarding career and make a meaningful impact on peoples’ lives in an environment that values your determination. Join our diverse, inclusive team and get ready to crush your goals!

OVERVIEW

We are seeking a player-coach, Systems Engineer Manager, to lead a small, high-impact team of system engineers while actively executing on core technical initiatives. This role requires a 60% hands-on engineering / 40% team management split. The ideal candidate will possess a strong technical background, proven leadership abilities, and a passion for delivering innovative solutions.

REPORTS TO

The Systems Engineer Manager reports to the Director, Technology Operations in the Technology department.

The ideal candidate is a deeply technical practitioner who thrives on solving complex system engineering challenges, driving backlog execution, and modernizing legacy systems into cloud-first, AI-augmented solutions. You will own our identity boundaries, endpoint management pipelines, workspace infrastructure, and edge services, while serving as a champion for AI-driven IT operations.

ESSENTIAL DUTIES

The essential duties for this role include, but are not limited to:

Team Management & Operational Leadership (40%)

• Team Management: Lead, mentor, and manage a team of 2-3 system engineers, ensuring the highest standards of quality and efficiency.
• Agile/Kanban Delivery & Metrics: Manage team backlog using Agile/Kanban best practices to establish clear priorities, maximize throughput, and maintain predictable delivery schedules. Track and maintain key operational metrics for monthly leadership reporting and capacity planning.
• Cross-Functional Partnership: Collaborate with leaders across Service Desk, Enterprise Applications, and DevOps to execute multi-departmental technical initiatives, establish seamless escalation paths, and drive shared operational efficiencies.
• Vendor Management & Managed Services Oversight: Direct operational and contract management for primary IT infrastructure partners-specifically YellowDog Networks (co-managed office networking, Palo Alto firewalls, switches) and core endpoint/identity vendors (e.g., Okta, JAMF, NinjaOne). Track vendor SLA compliance, oversee change validation protocols, manage contract renewals, and optimize licensing spend.

Hands-On Technical Execution (60%)

• Identity & Access Control (IAM): Architect, deploy, and maintain identity infrastructure across Active Directory (ADUC/GPO), Azure hybrid environments, Okta (SSO, Workflows, SAML, MFA), and Google Workspace (GSuite, Gemini access controls, Vault, GCP,GAM, API integrations) to enforce strict, HIPAA-compliant RBAC and zero-trust access controls.
• Endpoint & Workspace Systems Engineering: Own the lifecycle, system design, and security of physical and virtual endpoints (Windows and macOS) using NinjaOne, JAMF, PDQ SmartDeploy, WSUS, and AWS WorkSpaces. Modernize legacy deployment workflows into cloud-first solutions.
• AI-First Automation & Modernization: Actively write and maintain scripts (PowerShell, Bash, Python) using AI-assisted development platforms (e.g., Cursor) to eliminate manual IT toil, automate patch pipelines, and refactor legacy administrative processes.
• Network Access & Infrastructure Administration: Administer user-facing access policies and services, including Active Directory-integrated Radius Auth, GlobalProtect VPN user provisioning/client software, internal DNS, PKI/Certificate Authorities, AWS FSx / AWS File Gateway local storage, and Cisco voice/Jabber services. Partner with managed network providers (YellowDog Networks) to review, test, and validate global office network and Palo Alto firewall updates.
• Systemic Security & Vulnerability Remediation: Execute workstation endpoint encryption (BitLocker/JAMF) and proactively remediate endpoint OS and application vulnerabilities in close coordination with Information Security.
• Complex Cross-System Troubleshooting: Act as a primary technical escalation point. Lead root-cause analysis and resolution for complex, heavily integrated multi-departmental systems to minimize operational downtime.

Technical Expertise

• 8+ years of hands-on experience in systems engineering, endpoint management, and identity infrastructure, with at least 2 years in a management or lead capacity.
• Identity & Directory Services: Deep expertise in Active Directory, GPO, Azure AD Sync, Okta (SAML, Workflows, MFA), and Google Workspace Administration (OU management, Vault,GCP, GAM, security configurations, and user provisioning for enterprise tools like Gemini).
• Endpoint & VDI: Proven experience managing Windows and macOS environments at scale using JAMF, NinjaOne, PDQ SmartDeploy, and AWS WorkSpaces.
• Scripting & AI Tooling: Strong proficiency in PowerShell, Bash, Python or similar scripting languages, with demonstrated experience using AI-assisted coding platforms (e.g., Cursor, GitHub Copilot) to accelerate scripting and automation.
• Network & Storage: Solid understanding of DNS, PKI/Certificate Authorities, AWS FSx, AWS File Gateway, and core networking principles.

Leadership & Soft Skills

• Proven ability to operate effectively as a player-coach on a small team, balancing high-level planning with direct technical execution.
• Strong commitment to emotional intelligence, transparent communication, and collaborative problem-solving across teams.
• Experience managing IT projects via Jira/Confluence using Agile or Kanban frameworks.

Preferred Qualifications

• Certifications in relevant technologies (e.g., Okta Certified Administrator, Jamf Certified Admin, AWS Certified Solutions Architect, Microsoft Certified: Identity and Access Administrator).
• Experience in healthcare or regulated environments subject to HIPAA compliance.

• Competitive compensation Medical, Dental and Vision benefits after a short waiting period
• 401k matching program
• Generous paid time off program with an additional company break during the holidays
• Annual Volunteer Time Off (VTO) and a donation matching program
• Life Insurance Employee Assistance Program (health & well-being on and off the job) Rewards and Recognition
• Maternity and Parental Leave Training program and ongoing support throughout your entire Spring Venture Group career
• Diverse, inclusive & welcoming culture
• Optional enrollment options include HSA/FSA, AD&D, Spousal/Dependent life insurance, Short Term/Long Term Disability, Travel Assist, and Legal plans

Spring Venture Group is an Equal Opportunity Employer

Spring Venture Group is an Equal Opportunity Employer