Principal Software Engineer (Payments)

About Plusgrade

Travel is not just about the destination; it's about every memory made along the way. We partner with 250+ airline, hospitality, cruise, passenger rail, and financial services companies to create new, meaningful revenue streams through exceptional customer experiences. We value ambition, innovation and collaboration, and strive to build a bright future in travel.

About the Role

We are seeking a Principal Software Engineer (Payments) to technically lead our Payments team and help us build robust, scalable and secure payment capabilities for our travel partners and their customers. This role is based in our Montreal office and is part of the Payments team, responsible for productizing and centralizing payment processing across Plusgrade's growing business units to streamline operations and unlock new revenue opportunities.

As Plusgrade expands, the Payments team plays a critical role in modernizing and unifying how transactions are executed across the platform. You will work on core services that power high-volume, mission-critical payment and fulfillment workflows, while partnering with other business units (SBU, PBU, HABU) to deliver shared, scalable payment capabilities.

In this role, you will design and build services that handle complex business logic, integrate with multiple PSPs, and ensure reliability, security, and performance at scale. Your work will directly impact payment acceptance rates, user experience, and revenue across our products. You will work closely with product managers and engineers across the stack to build and deliver new payment products and features for airlines and travelers, while mentoring and upskilling engineers within and beyond your team.

What You Will Be Doing

You will join a team responsible for some of the most critical systems in the company, where ownership, quality and impact matter. This is an opportunity to shape how airline commerce is executed at scale, while building resilient systems that move real revenue every day.

• Provide technical leadership for the Payments team, taking ownership and driving high-quality products and features that create clear business value in an Agile environment.
• Act as the principal architect for payments: design and evolve end-to-end payment flows and services, ensuring they are secure, resilient, scalable and cost-effective.
• Participate in and often lead Architecture Assessments & Reviews as a subject matter expert for payment initiatives and integrations.
• Serve as the technical SME for payments with deep expertise across authorization, capture, refunds, reconciliation, tokenization, risk/fraud signals, and settlement.
• Own the design and implementation of PSP integrations, including orchestration across multiple PSPs, routing logic and failover strategies.
• Define and drive best practices for PSP integration patterns (API contracts, idempotency, error handling, retries, webhooks) to ensure consistency and reliability across providers.
• Collaborate with Product, Security, Compliance and Finance to ensure payment systems meet industry standards and regulations.
• Proactively identify and solve important problems, making balanced trade-offs for the whole system and business value.
• Promote OOP, clean code practices and design patterns; maintain high quality, reliability and maintainability of code in payments and beyond.
• Research and evaluate new technologies, tools and payment solutions to improve the platform and accelerate delivery.
• Provide support and guidance to less experienced peers, acting as a mentor and role model for engineers across multiple teams.

You Are Someone With

• 8+ years of relevant software development experience, including significant time as a senior or staff engineer responsible for complex distributed systems.
• Extensive experience designing and implementing software in Java (Spring) and knowledge of modern frontend technologies (e.g., TypeScript and React) in a full-stack or API-centric environment.
• Payments domain expertise, including hands-on experience integrating with multiple PSPs (design, build and maintenance of PSP integrations and payment orchestration) and deep understanding of payment flows (auth/capture/refund/void), reconciliation and operational considerations for high-volume systems.
• Proven experience leading technical teams or large initiatives with a delivery-focused mindset; experience using a cloud platform (AWS preferred) and deploying/operating in the cloud (e.g., AWS ECS, EKS, GCP) with Docker and observability tools (Datadog).
• Experience building secure, reliable, performant, scalable and cost-effective cloud applications in production.
• Strong SDLC and Agile practices with a track record of shipping well-tested, high-quality features rapidly.
• Exceptional debugging and problem-solving skills with a passion for elegant solutions to complex problems.

Nice to Have

• Experience with multiple cloud providers (AWS, Azure, GCP).
• AWS certifications or other major cloud certifications.
• Experience with machine learning/AI and understanding of big data concepts and analytics in a transactional/payments context.

What You'll Love About Us

• RRSP/401(k) Matching
• Comprehensive health plans
• Flexible Paid Time Off
• Annual travel allowance
• Annual wellness credits
• Team events and monthly lunches
• Equipment/commute allowance
• Remote work flexibility
• Parental Leave Top Up
• Adventure Pass

Our Process

Plusgrade is an equal-opportunity employer and is committed to providing an accessible recruitment process. We welcome applications from all qualified individuals and are committed to equal employment opportunities regardless of gender identity or expression, race, ethnic origin, creed, origin, age, sex, marital status, disability, sexual orientation, or other protected status. If needed, we provide accommodations for applicants with disabilities.

We believe in diversity and inclusivity and that is why our interview process is designed to provide a positive candidate experience and ensure every candidate is evaluated equally.

If you have a language preference for interviews, please inform our Talent team when they reach out.

All applications will be reviewed by our Talent Team and the successful candidate(s) will go through the following recruitment steps: Recruiter phone interview, Hiring Manager interview, take-home assessment or remote coding exercise, Team interview. All candidates will receive feedback, and all information will be kept confidential.