Staff DevOps Engineer

Who We Are

KEV builds mission-critical financial software for K12 schools across North America. Our platform provides real-time visibility and control over how funds are collected and managed, replacing fragmented workflows with secure, modern systems that schools rely on every day.

Trusted by more than 27,000 K12 schools managing over $8B annually, KEV delivers mission-critical software for payments, accounting, and reporting, where reliability and security matter.  Headquartered in Toronto with teams across North America, we are scaling quickly and investing deeply in cloud-native, data-driven technology.

KEV is a place for people who care about building durable software at scale and doing work that has real impact in public education. We focus on solving hard problems, raising the bar on engineering craft, and building products that earn long-term trust from the communities we serve.

This role is for an active vacancy.

About the Role

We are hiring a Staff DevOps Engineer to lead the modernization of KEV's infrastructure and delivery practices, taking us from where we are today to a platform built on infrastructure as code, templated CI/CD, and self-service golden paths for engineering teams. This role requires deep hands-on experience and the judgment to assess our current state honestly, shape a pragmatic modernization strategy, and break that strategy into work a team can actually execute.

You will operate as both a senior technical practitioner and a force multiplier: writing and reviewing the automation yourself while also coaching and upskilling existing team members. This is a role for someone who partners easily across the organization — with engineering leads and managers day to day, and with finance, revenue, product, and the Vice President of Architecture and CTO when infrastructure decisions have cost, risk, or roadmap implications — rather than treating platform modernization as an engineering-only initiative.

How You Will Contribute

Infrastructure Modernization Strategy & Execution 
Assess the current state of KEV's infrastructure and delivery practices, identify where legacy operations are creating risk or slowing teams down, and build a clear, sequenced strategy for modernizing them. Break that strategy into concrete workstreams, and lead a team through execution — balancing speed against risk and communicating trade-offs to stakeholders as priorities compete.

Infrastructure as Code & Platform Engineering 
Design and build the infrastructure-as-code foundations and templated, reusable CI/CD pipelines that let application teams ship reliably without re-solving the same infrastructure problems. Establish golden paths and platform engineering practices that make the right way to build and deploy the easy way, removing any manual, one-off work.

Azure & .NET Delivery Automation 
Own and improve how KEV's .NET services are built, deployed, and operated within Microsoft Azure, automating deployment pipelines and Azure-native infrastructure so releases are fast, predictable, and low-risk. Bring deep Azure expertise to decisions about how workloads should be architected and delivered going forward.

Site Reliability & AI-Enabled Operations 
Apply SRE practices — service-level objectives, reliability engineering, incident response — to raise the bar on how KEV's platforms are operated in production. Evaluate and apply AI tooling where it can meaningfully improve engineering and operational workflows, bringing the same trade-off thinking to new tooling that you'd apply to any other infrastructure decision.

Developer Experience 
Improve the day-to-day experience of engineers working on KEV's platforms, including local development environments and the tooling that supports them. Treat DevEx as a lever for velocity and quality, not a nice-to-have, and use feedback from engineering teams to prioritize what to fix next.

Coaching & Technical Mentorship  
Coach and mentor existing team members, helping them build fluency in infrastructure as code, CI/CD, and platform engineering practices. Raise the technical bar of the team through hands-on pairing, review, and knowledge-sharing, not just through documentation.

Cross-Functional Partnership & Communication  
Partner effectively with engineering leads, managers, and the Vice President of Architecture and CTO, as well as functions like finance, revenue, and product, translating technical modernization work into terms each audience cares about — cost, risk, timeline, or impact on delivery. Communicate clearly and proactively so that stakeholders across the business understand what's changing, why, and what trade-offs were made.

Who You Are

• 10+ years of hands-on experience in DevOps, Platform Engineering, SRE, or a similar infrastructure/engineering role, with a track record of leading the modernization of infrastructure operations into a DevOps model.

• Demonstrated experience designing and rolling out infrastructure as code, templated/reusable CI/CD pipelines, and platform engineering practices such as golden paths, at an organizational scale.

• Experience assessing the current state of an organization's infrastructure and delivery practices, building a modernization strategy from that assessment, breaking it into executable work, and leading a team through delivery.

• Strong hands-on experience with the Microsoft Azure ecosystem, including contributing to and automating the deployment of modern and legacy .NET services.

• Experience applying Site Reliability Engineering practices to production systems and experience evaluating and adopting AI tooling to improve engineering or operational workflows.

• Experience improving developer experience, including local development environments and developer-facing tooling.

• Experience working in a regulated environment - PCI, SOC 2, ISO 27001, HIPAA, HITRUST

• Solid understanding of security principles in complex ecosystems and proficiency with debugging and diagnostic tools to resolve application issues effectively.

• Demonstrated ability to coach and mentor engineers, raising the technical capability of a team over time.

• Strong ability to think in trade-offs — technical, cost, timeline, and risk — and to make and explain those trade-offs to both engineering and non-engineering audiences.

• Excellent communication skills, with proven ability to partner across organizational boundaries

What We Offer

• Competitive compensation – We believe in rewarding great work with fair, competitive pay.

• Meaningful benefits– Because your well-being matters; both at work and at home.

• Retirement Savings Support – We help you plan for your future with company-matched programs, including RRSP matching in Canada and 401(k) contributions in the U.S.

• Professional development – We invest in your growth with ongoing learning, stretch opportunities, and continuing education, including KEV Academy for onboarding and skill-building, plus KEV University, our online platform offering a wide range of courses.

• Hybrid model – 3 days in the office to collaborate and connect, with flexibility the rest of the week.

• Flexible PTO – Take the time you need to recharge with close to 4 weeks of vacation and a company-wide holiday closure

• Office perks – Enjoy a fully stocked snack bar and occasional catered lunches—because we know that great conversations (and ideas) often start around good food.

Salary Range - $150,000-180,000 

Note: We set standard base pay ranges for all roles based on function, level, and country location, benchmarked against similar stage growth companies. Final offer amounts are determined by multiple factors, including skills, depth of work experience and relevant licenses/credentials, and may vary from the amounts listed above.