Head of Technical Operations

Basic Job Details

Job Type: Full Time
Work Model: Hybrid
Remote Days: Monday & Friday
Office Days: Tuesday, Wednesday, Thursday

Responsibilities

• Leadership & Team Development:
  • Lead and mentor a high-performing Production Support Engineering team, fostering a culture of ownership, empathy, and continuous improvements
  • 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

Minimum Qualifications

• 8+ years of experience in IT, 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
• Hands-on experience administering enterprise IT systems (Google Workspace, Slack, AWS, MDM, SSO/identity, office A/V/networking)
• Hands-on experience with monitoring and alerting systems (Prometheus, Grafana, Sentry, DataDog, etc.)
• 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
• Comfort navigating large, matrixed organizations (experience working across multiple teams, getting alignment, and influencing without authority)
• Deep empathy for employees and customers, with commitment to delivering exceptional support experiences even under pressure

Preferred Qualifications

• Experience with QA or test automation
• Experience building or managing 24x7 support operations
• Experience transitioning support teams toward SRE or Technical Solutions Engineering models
• Hands-on experience administering both Microsoft 365/Teams/Azure and Google Workspace/Slack/AWS environments and making them play well together
• Experience with enterprise security and compliance policy definition and implementation
• Experience in logistics, supply chain, or freight technology