Head of Technical Operations

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

We’re looking for our first Technical Support Leader to 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. This role blends strategic execution, people leadership, and operational rigor. This is ideal for someone who thrives in ambiguity, enjoys building from 0-1, and cares deeply about reliability, customers, and engineering velocity.

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
  

Minimum Qualifications

• 7 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
• Strong technical background with deep understanding of cloud infrastructure, CI/CD, containerization (Kubernetes, Docker), and observability tools
• Hands-on experience with monitoring and alerting systems (Prometheus, Grafana, Sentry, DataDog, etc.)
• Track record of building 0-to-1 support functions where you owned both the "what" and the "how"
• Strong program management skills to lead cross-functional initiatives and drive projects to completion
• Proven ability to operate independently in ambiguous environments, defining strategy and executing without extensive guidance from leadership
• Experience operating in enterprise or high-scale B2B SaaS environments where reliability, compliance, and customer SLAs are non-negotiable
• Comfort navigating large, matrixed organizations (experience working across multiple teams, getting alignment, and influencing without authority)
• Deep empathy for customers, with commitment to delivering exceptional support experiences even under pressure
  
  

Preferred Qualifications

• Experience in logistics, supply chain, or freight technology
• Background in QA or test automation
• Previous experience building or managing 24x7 support operations
• Experience transitioning support teams toward SRE or Technical Solutions Engineering models
• Front-end experience (React, TypeScript) for handling lightweight UI fixes
• Experience in Fortune 500 or large enterprise tech organizations, particularly in roles requiring cross-functional alignment and executive communication
• Fluent in Spanish
  
  

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.