VP Engineering - Infrastructure & SRE

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.

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).
• 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.
• Promote 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-party resilience.
• Communicate crisply with executives, the board, and auditors, translating infrastructure risk, investment, and posture into business terms.

Minimum Requirements

• 15+ years of combined experience across infrastructure, platform, site reliability, software development, or related engineering disciplines, with substantial depth in infrastructure, including 5+ years leading engineering teams.
• Deep, hands-on expertise with AWS: you have designed and operated production architectures across compute, networking (VPC design, Transit Gateway, PrivateLink), IAM, and multi-account organizations at scale.
• Deep, hands-on expertise with Kubernetes in production: cluster lifecycle management, workload architecture, scaling, and the operational realities of running business-critical services on it (EKS experience strongly preferred).
• Deep expertise with relational databases at scale, specifically RDS/Aurora (MySQL and/or Postgres): high availability, replication, failover, performance tuning, and backup/recovery you have personally verified under pressure.
• Proven ownership of disaster recovery and business continuity for a production platform: you have defined RTO/RPO targets, built the capability to meet them, and run real failover tests, not just written the document.
• Demonstrated AI-forward leadership: you actively use AI tooling in engineering or operations work today, have opinions grounded in practice about where it helps and where it doesn't, and have led (or are visibly leading) a team's adoption of AI-assisted workflows.
• Track record of operating a 24/7, high-availability platform where downtime has direct revenue or customer impact, including mature incident command and postmortem practices.
• Willingness to manage and participate in an on-call rotation, and demonstrated ability to lead recovery from a full production outage: forming and testing hypotheses from logs, metrics, and traces rather than guesswork, making the right call quickly with incomplete information, and knowing when to mitigate first and root-cause later.
• Still technical, by choice: you remain a credible hands-on engineer, comfortable in a terminal, reading dashboards, and reviewing designs, and you expect to stay that way. You will lead the team and work alongside it; this is not a delegation-only role.
• Experience owning significant cloud budgets and driving cost efficiency without sacrificing reliability.
• Strong grounding in infrastructure-as-code (Terraform or equivalent) and modern CI/CD practices.
• Demonstrated ability to hire, develop, and retain strong infrastructure and SRE talent, and to hold a high bar through growth.

Preferred Knowledge and Skills

• Direct experience supporting PCI-DSS and SOC 2 programs from the infrastructure side: scoping and segmentation, control ownership, evidence automation, and working sessions with assessors and auditors.
• Experience in fintech, payments, or banking, especially in environments with heightened regulatory expectations (bank partnerships/sponsorships, FFIEC examinations, GLBA, or similar).
• Experience deploying AIOps or LLM-based tooling in production operations, such as AI-assisted incident response, intelligent alerting, automated runbooks, or agents (e.g., Claude Code or custom LLM integrations) embedded in SRE workflows, with sensible guardrails around safety and auditability.
• Experience with multi-region and active-active architectures, chaos engineering, and formal operational resilience programs.
• Familiarity with service mesh, zero-trust networking, secrets management, and workload identity patterns.
• Experience with CI/CD pipelines, progressive delivery (canary/blue-green), and platform engineering / internal developer platform approaches.
• Experience presenting to boards, auditors, or examiners, and building the documentation and evidence culture that makes those conversations easy.