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Head of Technical Operations

San Francisco, California, United States

Who We Are

Baton is Ryder’s in-house product development group focused on harnessing emerging technologies to redefine transportation and logistics. With $10B in freight under management, our technology reaches every part of the U.S. economy.

We design and ship category-defining software that enables Ryder and its 50,000+ customers—including some of the world’s most well-known brands—to plan and execute freight intelligently, efficiently, and cost-effectively. Our work includes everything from customer-facing software to the data platform that will power the next era of innovation at Ryder.

Baton’s mission: enable supply chain on autopilot.

Ryder acquired Baton in 2022 to power its next wave of digital products. We operate at startup speed, with Fortune 500 reach. If you have a passion for solving complex problems and creating impact for the engine of the American economy, you’ll love it here.

Role: Technical Director of Operations

Location: Hayes Valley, San Francisco, CA

Basic Job Details

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

Job Description

Baton is looking for a Head of Technical Operations to help us scale. This role sits at the intersection of engineering operations, customer reliability, and enterprise IT. It is ideal for a technical leader who thrives in ambiguity, cares about both internal and external customers, and can operate strategically while staying hands-on when needed.

You will own the vision, strategy, and execution of Baton’s Production Support function, ensuring platform reliability, operational excellence, and exceptional customer experiences as we scale. You’ll lead and grow a team of Production Support Engineers, and establish Baton’s technical support function as a strategic partner to Engineering, Product, and Customer Success.

You will also own the vision, strategy, and execution of Baton’s internal IT environment. Baton operates as an independent subsidiary with our own technology stack (Google Workspace, Slack, AWS) while being part of Ryder's enterprise environment (Microsoft 365, Teams, Azure). You will manage and improve our day-to-day systems while acting as a strategic bridge between Baton and Ryder's enterprise IT organization.

Responsibilities

  • 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

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

The Perks

  • Competitive Base Salary + Cash Bonus Structure
  • Annual Company Bonus + Long Term Incentive Plan
  • 401k with Matching
  • Hybrid Work Schedule
  • Hyper-Stable, publicly traded Enterprise
  • Medical, Dental, and Vision Health Coverage
  • Employee Stock Purchase Program (15% discount to market value)
  • Collaborative, Fun, and Tech Forward office in Hayes Valley, San Francisco, CA

Compensation Range: The annual base salary range for this position is $180,000- $230,000*. Compensation will vary based on factors including skill level, proficiencies, transferable knowledge, and experience. In addition to base salary, Baton's full-time employees are eligible for an annual performance bonus.

Why You Should Join

  • Have an immediate impact:
    • With Ryder’s existing customer base of 50,000+ companies and an internal headcount of 43,000, the scale and impact of our products will be large and far-reaching, from day one.
  • Opportunity to grow and lead in a Fortune 500 company:
    • You’ll get to work in a rapidly growing, startup-like environment while having the stability and backing of Ryder and its full executive team.
  • Creative, fast-paced environment to solve impactful problems in Supply Chain:
    • We’re going to design completely new tools for an industry that hasn’t been rethought in decades. And to do this, we need people who think differently.

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