Jobs at Bridgeway Benefit Technologies

Build and operate production AI capabilities using Python, LLMs, retrieval, and intelligent automation. Responsibilities include integrating LLM APIs, developing retrieval-augmented features, creating evaluation and prompt frameworks, applying security and compliance controls, monitoring production systems, and collaborating across engineering, data, security, product, and operations teams.

Owns full-cycle net-new enterprise SaaS sales across public sector pension systems. Responsibilities include prospecting, territory strategy, RFP and procurement navigation, executive and board presentations, demos, negotiations, forecasting, CRM management, and closing complex multi-stakeholder deals. The role collaborates with sales, marketing, customer success, and product teams, requiring strong public sector sales expertise and travel for finalist presentations, conferences, and customer visits.

Provides Tier 1 technical support and system administration across Windows, Linux, networking, identity, endpoints, Microsoft 365, Azure Virtual Desktop, and customer hosting environments. Responsibilities include ticket triage, incident command, access provisioning, patching, backups and restore testing, security-policy compliance, audit evidence, remote-access administration, troubleshooting, knowledge-base development, and Bash/PowerShell automation. Participates in on-call support and communicates technical issues clearly to users, customers, and executives.

Provides Tier 1 IT support and system administration across Windows and Linux environments. Manages tickets, endpoints, Microsoft 365, identity and access, VPNs, Azure Virtual Desktop, customer hosting support, patching, backups, and incident response. Supports onboarding, audits, access reviews, and privileged credentials while maintaining documentation and automating routine tasks with Bash and PowerShell.

Supports cloud infrastructure design, maintenance, monitoring, and automation. Assists with infrastructure as code, CI/CD pipelines, observability, patching, incident response, disaster recovery, security controls, cost optimization, and platform support. Contributes to runbooks, root-cause analysis, documentation, Agile delivery, code reviews, and Tier 2 on-call support while collaborating with development, operations, and security teams.

Lead customer-facing enterprise software implementations from kickoff through go-live and transition to support. Manage project scope, plans, budgets, schedules, resources, risks, forecasts, documentation, stakeholder communications, requirements, proposals, training, and knowledge transfer. Coordinate across professional services, sales, support, engineering, and technical teams to deliver projects on time and within budget while improving implementation processes and portfolio efficiency.

Leads compensation, benefits, and HR operations, including merit cycles, pay equity, benefits administration, compliance, vendor management, HRIS data integrity, workforce cost analysis, and process improvement. Advises senior leaders on total rewards strategy, manages an HR Operations Specialist, supports human capital projects, and uses AI tools to improve workflows and productivity.