Sezzle - VP Engineering - Infrastructure & SRE

• 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. • 15+ years • 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 AWS • 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, hands-on expertise with Kubernetes in production • 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. • Deep expertise with relational databases at scale • RDS/Aurora (MySQL and/or Postgres) • 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. • Proven ownership of disaster recovery and business continuity • 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. • Demonstrated AI-forward leadership • 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. • operating a 24/7, high-availability platform • 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. • Willingness to manage and participate in an on-call rotation • lead recovery from a full production outage • 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. • Still technical, by choice • Experience owning significant cloud budgets and driving cost efficiency without sacrificing reliability. • owning significant cloud budgets • Strong grounding in infrastructure-as-code (Terraform or equivalent) and modern CI/CD practices. • infrastructure-as-code • Demonstrated ability to hire, develop, and retain strong infrastructure and SRE talent, and to hold a high bar through growth. • Bachelor's degree in Computer Science or a similar technical field (required). • 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. • Direct experience supporting PCI-DSS and SOC 2 programs • Experience in fintech, payments, or banking, especially in environments with heightened regulatory expectations (bank partnerships/sponsorships, FFIEC examinations, GLBA, or similar). • fintech, payments, or banking • heightened regulatory expectations • 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. • AIOps or LLM-based tooling in production operations • Experience with multi-region and active-active architectures, chaos engineering, and formal operational resilience programs. • multi-region and active-active architectures • Proficiency with modern observability stacks (Prometheus, Grafana, Loki, Tempo, or commercial equivalents) and driving observability as a platform capability. • modern observability stacks • Familiarity with service mesh, zero-trust networking, secrets management, and workload identity patterns. • service mesh, zero-trust networking, secrets management, and workload identity • Experience with CI/CD pipelines, progressive delivery (canary/blue-green), and platform engineering / internal developer platform approaches. • CI/CD pipelines • Experience presenting to boards, auditors, or examiners, and building the documentation and evidence culture that makes those conversations easy. • boards, auditors, or examiners • You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed. • You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things • You’re not bound by convention • You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking. • You need action • You earn trust - you listen attentively, speak candidly, and treat others respectfully. • You earn trust • You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly. • You have backbone; disagree, then commit • You deliver results - you focus on the key inputs and deliver them with the right quality and in a timely fashion. Despite setbacks, you rise to the occasion and never settle. • You deliver results • Sezzle’s Technology Stack: • Languages: Golang, Typescript, Python • Languages: • Frontend: Typescript - React and React Native • Frontend: • Backend: Golang • Backend: • Database: MySQL, Postgres • Database: • DevOps & Cloud: AWS, Kubernetes • DevOps & Cloud: • Version Control: Git • Version Control: • CI/CD: • Testing: Developer and AI-driven, focus on automated end-to-end, integration, and unit tests • Testing: • Open Source: Sezzle is focused on using open source, and we build what we can before buying! • Open Source: • What Makes Working at Sezzle Awesome? • At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators; we are skilled musicians, yogis, cyclists, chefs, golfers, dog-lovers, and rock-climbers. We believe in surrounding ourselves with not only the best and the brightest individuals, but those that are unique and purpose-driven in all that they do. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire.