Head of Technical Operations

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Leadership & Team Development: Lead and mentor a high-performing Production Support Engineering team, fostering a culture of ownership, empathy, and continuous improvements Build and execute hiring, onboarding, and career development plans, establishing clear pathways for growth Create structured onboarding programs to accelerate context-building on Baton's products, tech stack, and business logic Foster deep integration between PSE and core engineering teams, breaking down silos and enabling knowledge sharing Operational Excellence: Design and implement comprehensive runbooks, processes, and operational documentation Establish and manage SLAs and key metrics (uptime, response time, resolution time, CSAT), driving continuous improvement through data Own customer and operator communication during incidents, ensuring clear, timely, and empathetic updates during outages and degradations Leverage customer insights, telemetry, and support trends to proactively detect issues, automate solutions, and advance support tooling Partner with Engineering to validate new features, run bug bashes, create E2E/integration tests in response to incidents, and support pre-onboarding QA for customer migrations Strategic Initiatives: Define the team’s charter, transforming Production Support towards a hybrid Site Reliability Engineering (SRE) / Technical Solutions Engineering model Partner with Engineering and Product leadership to influence platform reliability, observability tooling, and self-service capabilities—ensuring Baton's infrastructure can scale to support Ryder's 50K+ customers Define and execute a roadmap toward 24x7 coverage, reducing external help desk dependencies as the business scales Establish processes for the PSE team to take on customer-specific technical solutions, configuration changes, and lightweight operational fixes—protecting engineering bandwidth for strategic roadmap work Champion exceptional customer experiences: Use incident trends and customer feedback to drive platform improvements that prevent future issues and increase customer satisfaction Enterprise IT Administration : Manage and administer Baton's core IT systems including Google Workspace, Slack, AWS, related productivity tools, MDM, office A/V, and our office internet/WiFi Develop and implement strategies for bridging Baton and Ryder systems where appropriate, including SSO, identity management, and cross-platform workflows Act as primary technical liaison with Ryder's enterprise IT team, navigating policies, security requirements, and integration opportunities Build relationships with Ryder IT leadership to advocate for Baton's needs while ensuring alignment with enterprise standards Evaluate opportunities to migrate Baton systems to Ryder's enterprise platforms where it makes business and technical sense Create and maintain policies, procedures, and documentation for Baton's IT environment that are aligned with Ryder’s security and compliance policies Provide hands-on IT support to Baton employees Identify opportunities for automation and integration, partnering with engineering teams as needed to execute on these opportunities Who You Are Required Qualifications 8+ years of experience in technical support, DevOps, or Site Reliability Engineering 5+ years of experience managing and scaling production support teams in high-growth B2B SaaS environments where reliability, compliance, and customer SLAs are non-negotiable Strong program management skills to lead cross-functional initiatives and drive projects to completion Strong change-management skills, with a track record of rolling out new systems with minimal disruption and high employee adoption Experience navigating enterprise procurement, security, compliance, and change-control processes Hands-on experience with monitoring and alerting systems (Prometheus, Grafana,