(Remote) Senior Manager, Operations

Legacy System Remediation & Platform Transition

Assess the current legacy environment against industry-standard operational practices (security posture, patching/lifecycle management, monitoring, automation, documentation) and lead the remediation effort to close identified gaps.
Prioritize and execute legacy upgrades in a way that manages risk to live state, federal, and pharmacy clients - balancing stability with the pace of improvement.
In parallel, design the Operations support model (DevOps, Platform, and IT support structure, tooling, staffing, and processes) for the new modern platform as it is built and rolled out.
Plan and manage the transition period in which legacy and modern platforms run side by side, including staffing, cost, and client-impact implications of supporting both.
Partner with Product and Engineering leadership to ensure the new platform is being built with operational supportability (observability, automation hooks, deployment practices) in mind from the start.
Provide the VP with a clear roadmap and cost picture for the legacy-to-modern transition, including where legacy remediation spend can be reduced or redirected as the new platform matures.

Team & Operational Leadership

Lead and develop the DevOps, Platform, and IT teams, including hiring, performance management, and career development for team leads and engineers.
Own day-to-day execution across infrastructure, platform reliability, internal IT services, and DevOps practices (CI/CD, automation, monitoring, incident response).
Establish and report on operational metrics: uptime/availability, MTTR, ticket SLAs, change failure rate, and infrastructure cost per environment.
Drive process improvement and tooling decisions that increase efficiency and reduce operational risk, consistent with STChealth's compliance obligations (SOC 2, state security requirements, federal client expectations).

Contract & Vendor Management

Own the full lifecycle of contracts for tooling and vendors used within Operations (cloud infrastructure, monitoring, ITSM, identity/security tooling, etc.), including renewals, usage tracking, and total cost of ownership.
Partner directly with the VP, Support Services on contract negotiations for Operations-related vendors, bringing usage data, cost modeling, and risk assessment to the table.
Identify consolidation, renegotiation, or replacement opportunities that reduce cost or improve terms without compromising reliability or compliance.
Maintain a clear, current view of all active contracts, renewal dates, and cost exposure within the Operations portfolio.
Work with Security to ensure all environments are within policies and standards.

Cross-Functional Partnership

Act as a trusted advisor to the VP on budget planning, forecasting, and resourcing decisions for the Operations function.
Build strong working relationships with Sales, Product, and Customer Success to ensure Operations capacity and cost realities are reflected in commitments made to clients.
Represent Operations in internal planning conversations involving new client onboarding, contract renewals, and service expansions.
Provide input into sales deal structuring when Sales is pricing custom or complex client requests that involve Operations effort or infrastructure.