Systems Engineering Lead (Hybrid)

Job Overview

The Network & Systems Engineering Lead is a player-coach role responsible for the technical leadership and operational health of Rewards Network's network and systems infrastructure. This position combines direct people management of a small, senior engineering team with meaningful hands-on technical contribution, ensuring both day-to-day stability and longer-term infrastructure modernization. The role reports to the Senior Manager, Infrastructure & Site Reliability Engineering and collaborates closely with Security, SRE, DBA, and product engineering teams.

This is a hybrid position that requires in office presence 3 days a week (Tuesday-Thursday) in Chicago.

What you'll bring to the table: (Responsibilities)

• Lead, develop, and support a team of network and systems engineers; manage performance, career growth, and day-to-day prioritization while remaining technically engaged alongside the team.
• Architect, maintain, and continuously improve on-premises network infrastructure including routing, switching, firewalls, and physical datacenter topology.
• Own the health and reliability of Windows and Linux server environments, including patching cadence, configuration management, and OS lifecycle planning.
• Drive infrastructure modernization initiatives such as datacenter consolidation, network stabilization, and cloud expansion in partnership with the broader engineering organization.
• Lead or contribute to database platform migrations and integrations (MS SQL to PostgreSQL), partnering with DBAs and application teams on planning and execution.
• Collaborate with the AWS-focused SRE team to extend and mature the organization's cloud infrastructure, with emphasis on networking, security boundaries, and hybrid connectivity.
• Evaluate infrastructure hardware and software options with a cost-conscious, ROI-driven approach; partner with engineering leadership on procurement decisions and vendor selection.
• Establish and maintain runbooks, change control practices, and technical documentation to support reliable operations and audit/compliance requirements.
• Participate in incident response as an escalation point for network and systems issues; conduct root cause analysis and drive durable remediation.
• Manage and evolve virtualization and containerization platforms across on-premises and cloud environments, ensuring efficient resource utilization and alignment with broader infrastructure strategy.
• Contribute to infrastructure roadmap planning by surfacing technical risks, capacity needs, and modernization opportunities to engineering leadership.
• Own disaster recovery planning for network and systems infrastructure; define recovery objectives, maintain runbooks, and lead regular DR testing exercises to validate recoverability.

Do you have the right mix of ingredients

• 5+ years of hands-on experience in network engineering, systems administration, or a combined infrastructure role
• 2+ years in a lead or management capacity with direct reports
• Demonstrated experience with enterprise networking (routing, switching, firewalls, VLANs)
• Proficiency administering Windows Server and Linux/Unix environments
• Working knowledge of AWS or comparable public cloud platform
• Experience supporting or migrating relational databases (SQL Server, PostgreSQL)
• Strong written and verbal communication; able to translate technical concepts for non-technical stakeholders and leadership
• Effective prioritization and time management across people management, project work, and operational response
• Collaborative approach to cross-functional work with engineering, product, security, and finance teams
• Analytical and cost-conscious mindset when evaluating infrastructure decisions and vendor options
• Ability to operate independently and drive initiatives with minimal oversight in a fast-paced environment
• Commitment to documentation, operational rigor, and continuous improvement

Comprehensive benefits package, which includes

• This is a full-time, exempt position. The base salary range for this role in Chicago is $160,000-$200,000 annually, depending on managerial experience (lead and/or manager), as well as technical experience, skills, and other factors. This role is also eligible for an annual bonus target of 10% to 15%.
• Competitive Time Off Benefits: including flexible PTO, 11 company holidays, and parental leave.
• Generous dining reimbursement when you dine with our restaurant clients
• 401(k) plan with a company match
• Two medical plan options- Standard PPO or High Deductible Health Plan (HSA with company match for HDHP participants)
• Partnership with Rx n Go, offering certain prescriptions for free
• Two dental plan options and a vision plan
• Flexible Spending Accounts and a pre-tax commuter benefit program
• Accident, Critical Illness, and Hospital Indemnity Insurance Plans
• Short Term and Long Term disability
• Company-paid life insurance and AD&D insurance, supplemental employee, spouse, and child life insurance
• Employee Life Assistance Program
• Hybrid working environment in a new office space downtown near the Metra Train stations and catered lunches on Tuesdays.

Expected Pay Range $160,000 - $200,000 USD