VP Engineering - Infrastructure & SRE

About this role

The salary range for this role is negotiable, the range being $400,000 - $600,000 per year in total compensation.

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role:

We are seeking an exceptional VP Engineering - Infrastructure & SRE to own the strategy, reliability, security posture, and evolution of the platform that powers Sezzle. This is a rare opportunity to lead infrastructure through a defining chapter: scaling a high-growth fintech while raising our operational rigor, resilience, and compliance posture to the standards of the most demanding financial institutions.

This is explicitly both a leadership job and a technical one . You will lead the teams responsible for our cloud infrastructure, Kubernetes platform, databases, networking, observability, and site reliability engineering, and you will stay hands-on in the systems yourself, working alongside the engineers you lead. Our stack runs on AWS, with workloads orchestrated on Kubernetes and data anchored in Aurora RDS (MySQL and Postgres). You should know these technologies deeply, not just manage people who do. You will set the technical vision, own the budget, and be directly accountable for availability, disaster recovery, and business continuity across a payments platform where downtime has immediate customer and financial impact.

That accountability is personal, not just organizational: you will manage the on-call rotation and take shifts in it. When Sezzle experiences a serious incident, up to and including a full outage, you are the kind of leader who can step into command, cut through noise with evidence-based triage, make fast, sound decisions under pressure with incomplete information, and drive the platform back to health. Your team should trust you at 3 AM as much as they do in a roadmap review.

Just as importantly, you will lead our infrastructure organization into an AI-boosted SRE era. We believe the next generation of infrastructure teams will pair strong engineers with AI agents and tooling for incident response, capacity planning, runbook automation, anomaly detection, and day-to-day operational toil. You won't just tolerate this shift; you'll drive it, with conviction and hands-on credibility.

This role reports to senior engineering leadership and partners closely with Security, Compliance, Engineering, Finance, and external auditors. Your work will directly shape whether Sezzle can operate at the highest standards of reliability and compliance without losing the speed and pragmatism of a startup.

Key Responsibilities

• Own the infrastructure vision, strategy, and multi-year roadmap : scale today's high-growth fintech platform while continually strengthening its resilience, controls, and audit-readiness.

• Lead, grow, and mentor the infrastructure, platform, and SRE organization , including hiring, career development, on-call health, and building a culture of operational excellence and blameless learning.

• Own reliability end-to-end : define and enforce SLOs and error budgets, mature incident management and postmortem practices, and be accountable for platform availability across the business.

• Manage, and participate in, the on-call rotation , and serve as senior incident commander for high-severity events: leading recovery from major degradations and full outages through rapid, evidence-based triage, decisive action under uncertainty, and clear communication to stakeholders throughout.

• Direct our AWS strategy , including account architecture, IAM and network design, multi-AZ/multi-region posture, service selection, and cost management (FinOps). You will own and defend the cloud budget.

• Own the Kubernetes platform as a product: cluster architecture, upgrade strategy, workload isolation, autoscaling, progressive delivery, and the developer experience of every team that ships on it.

• Own the database tier , centered on Aurora RDS (MySQL and Postgres) : availability, performance, capacity, schema and migration safety practices, backup/restore verification, and encryption.

• Design, implement, and continuously test disaster recovery and business continuity : defined RTO/RPO targets per system tier, regular game days and failover exercises, and DR evidence that stands up to auditor scrutiny.

• Champion the AI-boosted SRE transformation : evaluate and deploy AI tooling and agents for incident triage, observability, runbook automation, and toil reduction; set standards for safe, auditable use of AI in production operations; and bring the team along through training and example.

• Partner with Security and Compliance to own infrastructure's role in PCI-DSS and SOC 2 : control design and operation, evidence collection, segmentation, vulnerability and patch management, and audit support, with the maturity to meet the expectations of banking partners and financial-industry examinations.

• Drive infrastructure-as-code and platform automation as the default: everything reproducible, reviewed, and recoverable; nothing artisanal.

• Own vendor and technology strategy for the infrastructure domain: build-vs-buy decisions, vendor risk management, contract negotiation, and third-par

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