Lead Software Engineer-Remote

Who We Are

Cimpress Technology develops cutting-edge, best-in-world software that powers our mass customization businesses and helps create personalized products for more than 17 million customers globally.

Our Mass Customization Platform is built on modular, multi-tenant services that allow our businesses to choose the solutions they need or combine them to create custom experiences. This helps them move faster — whether it’s launching new products, reaching customers, or managing and tracking orders.

We believe in giving our engineers the ownership and autonomy to make a real impact. Teams define their own roadmaps and choose the technologies and programming languages that best fit their needs. This allows us to operate at enterprise scale while retaining the agility, ownership, and entrepreneurial spirit of a smaller organization.

About the team

The CT Commerce domain is looking for a Lead Software Engineer to lead the Payments team. Payments is a business-critical platform responsible for enabling secure, reliable, and scalable payment experiences across multiple businesses and channels.

We are looking for a hands-on technical leader with strong experience in distributed backend systems, cloud-native architecture, and engineering leadership. In this role, you will shape the team’s technical direction, lead strategic initiatives, strengthen operational reliability, and help engineers grow into confident and independent owners.

If you are passionate about building resilient systems, solving complex engineering problems, and enabling teams to deliver high-quality software, we would love to hear from you.

What You Will Do

Technical Leadership and Architecture

Define the team’s technical direction and ensure alignment with the broader Payments Platform and CT Commerce strategy.

Design and evolve secure, resilient, scalable, and low-latency payment services and distributed systems.

Lead RFCs and Architecture Decision Records (ADRs) to evaluate, document, and communicate important technical decisions.

Make pragmatic technical trade-offs across scalability, reliability, performance, security, maintainability, and time to market.

Establish and strengthen engineering practices across architecture, development, testing, documentation, observability, security, and production readiness.

Team Leadership and Delivery

Lead, mentor, and develop engineers, fostering a culture of technical excellence, collaboration, accountability, and continuous growth.

Break complex initiatives into clearly owned workstreams, manage dependencies and risks, and drive cohesive production launches.

Partner closely with Product Managers and other engineering teams to clarify priorities, evaluate trade-offs, and communicate progress, risks, and technical decisions.

Facilitate Scrum ceremonies, retrospectives, and continuous-improvement initiatives that improve team effectiveness and delivery predictability.

Strengthen capacity planning, ownership, and operational readiness to support reliable and sustainable delivery.

Engineering Excellence and Reliability

Improve the reliability, performance, scalability, security, and operational resilience of the Payments Platform.

Drive strong practices around automated testing, CI/CD, infrastructure as code, code reviews, observability, and production readiness.

Improve incident response and on-call effectiveness while driving preventive actions to reduce recurring operational issues.

Promote a culture of end-to-end ownership, where engineers build, operate, measure, and continuously improve the systems they own.

Promote responsible AI-assisted and AI-driven engineering practices that deliver measurable improvements in productivity, quality, and operational effectiveness.

Individual Contribution

Contribute directly to the design, development, testing, deployment, and production support of distributed payment services.

Build secure, resilient, and low-latency payment capabilities and integrations with providers such as Adyen, Braintree, and PayPal.

Lead by example through thoughtful technical decisions, high-quality implementation, effective code reviews, and resolution of complex technical problems.

Collaborate with engineers and technical leaders across the organization to identify opportunities for simplification, reuse, modernization, and platform improvement.

What We Need

Strong Software Engineering Experience: A strong track record of building and operating reliable, business-critical backend services and distributed systems.

Technical and People Leadership: Demonstrated experience shaping architecture, leading complex initiatives, mentoring engineers, providing constructive feedback, and establishing clear ownership within teams.

Distributed Systems Expertise: Strong foundations in API design, microservices, event-driven architecture, distributed systems, data management, reliability, performance, security, and observability.

Cloud-Native Engineering: Experience designing and operating cloud-native systems and modern engineering practices, including automated testing, CI/CD, and infrastructure as code.

Hands-on Engineering: The ability and willingness to contribute directly to design, coding, testing, code reviews, deployment, and production support.

Technical Judgment: Ability to make pragmatic technical decisions and trade-offs in complex and ambiguous situations.

Collaboration and Communication: Strong communication skills with the ability to work effectively with engineers, product managers, technical leaders, and other stakeholders.

Team Development: Proven ability to coach and mentor engineers and create an environment where individuals can grow into confident and independent owners.

What Will Make Your Candidature Great

Experience building and operating high-volume, business-critical payment or financial systems.

Experience integrating with payment providers such as Adyen, Braintree, PayPal, or similar payment platforms.

Strong understanding of payment processing concepts such as transaction lifecycles, idempotency, retries, failure handling, reconciliation, and distributed-system consistency.

Experience improving platform reliability, observability, incident response, and on-call effectiveness.

Experience leading architecture evolution, modernization, or migration of large-scale distributed systems.

Experience using AI-assisted development tools and AI-driven engineering practices to improve engineering productivity, software quality, and delivery.

A passion for mentoring, knowledge-sharing, and contributing to the wider engineering community.

Experience working effectively in distributed teams and asynchronous collaboration environments.

Why You'll Love Working Here

This is a unique opportunity to lead and shape a business-critical Payments Platform, working alongside a diverse and talented team of engineers across Cimpress. You will have the opportunity to solve challenging distributed-systems problems, influence technical direction, and build platforms that enable critical customer experiences across multiple businesses.

At Cimpress, we give our engineers the autonomy to make meaningful technical decisions, learn continuously, and take ownership of the systems they build and operate. Through constant learning, collaboration, and exposure to what’s next, we encourage our people to keep pushing boundaries and broadening their horizons.

We put great importance on the wellbeing of our employees and strive to create an environment where people can grow, do meaningful work, and maintain a healthy work/life balance.

Led by founder and CEO Robert Keane, Cimpress invests in and helps build customer-focused, entrepreneurial mass customization businesses. Through the personalized physical and digital products these companies create, we empower over 17 million global customers to make an impression. The Cimpress family includes a dynamic, international group of businesses and central teams, all working to solve problems, build businesses, innovate, and improve.

Skills