Principal Technical Program Manager (Remote)

Here at Shippo, we are the shipping layer of the internet and we consider ourselves to be one of the core building blocks of e-commerce.

Our mission is to make merchants successful through world class shipping. With our products and solutions, we level the playing field by providing our customers with best-in-class solutions that otherwise wouldn’t be available to them. Through Shippo e-commerce businesses, marketplaces, platforms and a variety of logistics infrastructure providers are able to connect to shipping carriers around the world from one API and dashboard. We provide our customers with the most competitive shipping rates, print labels, automated international documents, shipment tracking, facilitate the returns process and more.

How we’ll deliver success:

We are seeking an exceptional Principal Technical Program Manager (TPM) who will join our Engineering Leadership team and be responsible for execution of developer experience, site reliability (SRE), product security, and cross-organizational programs. This role will drive strategic technical initiatives that enhance our developer productivity, system reliability, security posture, and engineering capabilities across the entire organization.

The Principal TPM will serve as a technical leader and strategic partner to engineering leadership, developer experience teams, SRE teams, security teams, and cross-functional stakeholders to define, prioritize, and execute programs that are foundational to our engineering excellence and operational resilience. Additionally, while not managing Program Managers directly, this role will lead the creation of organizational standards, templates, and best practices for program management, while mentoring program and technical program managers across the organization.

You will be responsible for programs that span multiple engineering teams, enhance our technical infrastructure, and directly impact our ability to scale efficiently, reliably, and securely.

• Drive initiatives that improve developer workflows, productivity, and satisfaction.
• Lead optimization of CI/CD pipelines, development environments, and tooling.
• Standardize onboarding processes, code review practices, and development workflows.
• Implement feedback systems (e.g., DORA metrics, surveys) to continuously improve developer experience.

• Partner with SRE teams to strengthen service reliability, scalability, and operational excellence.
• Lead efforts in capacity planning, disaster recovery, and performance optimization.
• Implement automation for infrastructure, monitoring, and incident response.
• Reduce MTTR through improved observability, alerting, and on-call practices.

• Coordinate security program rollouts across engineering teams to ensure SLA adherence.
• Promote secure development practices and integrate security-by-design into engineering processes.
• Drive adoption of security automation, tooling, and vulnerability management.
• Facilitate collaboration between Security Engineering and Product teams to align requirements and execution.

• Execute complex programs spanning multiple teams, business units, and geographies.
• Lead platform migrations, large-scale technology upgrades, and infrastructure modernization.
• Establish collaboration frameworks that align Engineering, Product, SRE, and Security teams.
• Break down silos and ensure unified execution of technical initiatives.

• Translate organizational objectives into clear technical programs with success metrics.
• Define governance frameworks, risk management processes, and reporting structures.
• Facilitate architectural decision-making and drive cross-team technical alignment.
• Provide visibility to stakeholders through program tracking and communication systems.

• Define and implement best practices, templates, and playbooks for technical program management.
• Scale program management frameworks across the organization for consistency and efficiency.
• Establish KPIs to measure program delivery effectiveness and drive continuous improvement.

• Mentor and coach Program Managers and Technical Program Managers.
• Support hiring, onboarding, and career development of program management talent.
• Lead communities of practice, knowledge-sharing forums, and skill development initiatives.

• 10+ years of experience on software teams as Software Engineer, Engineering Manager or TPM
• 6+ years in TPM role
• B.S. in Software Engineering, Computer Science, or Technical Discipline
• Experience defining, influencing and running end-to-end complex technical programs
• Strategic thinking and ability to understand complex technical concepts and communicate them to executive business stakeholders
• Ability to drive change through building systems, frameworks and/or platforms
• Understanding of capacity, systems efficiency and mapping return on investment to engineering systems
• Excellent writing skills to distill contextualized metrics, facts, and raise clear risks with paths to green, to business and engineering stakeholders
• Facilitate and make complex decisions to keep programs moving and on time
• Ability to thrive in fast-paced, collaborative and ambiguous start-up like environments where thoughtfulness, an entrepreneurial mindset, persistent execution and relationships drive success
• Experience in driving change across large >120 engineering organizations
• TPMs are not expected to write or read code, but are expected to understand system flows, system architectures, and APIs

• Experience in high-scale technology companies with complex engineering organizations
• Previous experience in program management leadership roles with responsibility for establishing standards and mentoring other PgMs
• Track record of building program management capabilities in growing organizations or during organizational scaling
• Hands-on experience with specific tools in our focus areas:
• Developer Experience: GitHub Actions, Docker, internal platform tools, developer portals, build systems, testing frameworks
• SRE: Prometheus/Grafana, NewRelic / Datadog, Kubernetes, Terraform, incident management platforms, observability tools
• Product Security: SIEM platforms, vulnerability scanners, security automation tools, static analysis tools, threat modeling platforms
• Cross-Organizational Programs: Program management tools, migration frameworks, incident response platformsExperience with agile/lean methodologies and modern program management tools (Jira, Asana, etc.)Background in DevOps, Platform Engineering, or Infrastructure Engineering roles
• Experience managing technical programs in regulated industries or with strict compliance requirements
• Experience mentoring PgMs and creating best practices
• Experience with organizational change management and large-scale engineering transformation initiatives

• Healthcare coverage for medical, dental, and vision (90% covered by the company, incl. dependents). Pets coverage is also available!
• Take-as-much-as-you-need vacation policy & flexible working 
• One week-long company wide winter shutdown 
• 3 Volunteer Days Off (VTOs)
• WFH stipend to set up your home office
• Charity donation match up to $100
• Dedicated programs, coaching, tools, and resources for your professional and career growth as well as an individual learning stipend for your personal and focused growth
• Fun team in person time through our Shippos Everywhere program which includes regular team and company off-sites throughout the year as well as local Shippos gatherings

Our Compensation Shippolicy:

We believe compensation is a custom experience and are commited to fair and equitable compensation practices. The standard base pay range for this role is min is $212k to a max $287k annual salary. Since we are focused on hiring Shippos Everywhere, we have 2 US pay ranges, a standard compensation range for the majority of the US and a standard +1 compensation range for those who live in areas where the cost of labor is higher, such as NYC and California.

The actual base pay is dependent upon many factors, such as: financial budgets, work experience, training, transferable skills, business needs, and market value. The base pay salary ranges are subject to change and may be modified in the future. Total compensation for this role will include, equity, medical, dental, vision and other benefits noted in our Shippos “package” section.

Sail through the process:

Here at Shippo, we celebrate inclusivity and are committed to creating equal access to opportunities for people from all backgrounds, perspectives and geographies. These values define who we are and everything we do. All qualified individuals are encouraged to apply. If you need assistance, or a reasonable accommodation during the application and recruiting process, please contact us at [email protected]

Shippos in the wild:

Our people, much like the packages we help ship, are all over the world. This means, through our remote-first program, “Shippos Everywhere”, our roles can be based anywhere in the US with the exception of Delaware, Nevada, Ohio, Oregon, Hawaii, New Mexico and West Virginia and many roles can be based internationally.

For locations outside of the US and Ireland, the employment contracts are powered by Remote.com (all Shippo perks still apply - including equity!). What we want to emphasize is that you can be successful at Shippo regardless of location.

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We leverage AI to review all resumes during the application phase to ensure fairness, comprehensively evaluate each submission, and mitigate bias. However, all decisions at every stage of the process are made by a real person.