Engineering Manager, CRM Systems

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-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. * Bachelor's degree in Computer Science or a similar technical field (required). 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. * Proficiency with modern observability stacks (Prometheus, Grafana, Loki, Tempo, or commercial equivalents) and driving observability as a platform capability. * 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. About You: * 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 need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking. * You earn trust - you listen attentively, speak candidly, and treat others respectfully. * 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 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. Sezzle’s Technology Stack: * Languages: Golang, Typescript, Python * Frontend: Typescript - React and React Native * Backend: Golang * Database: MySQL, Postgres * DevOps & Cloud: AWS, Kubernetes * Version Control: Git * CI/CD: Gitlab * Testing: Developer and AI-driven, focus on automated end-to-end, integration, and unit tests * Open Source: Sezzle is focused on using open source, and we build what we can before buying! 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. Perks & Benefits:  * Unlimited PTO, volunteer hours and sabbatical  * Life, STD/LTD, medical, dental and vision insurance  * Highly discounted LifeTime gym membership * 401k with match * Collaborative fun co-workers * The opportunity to join the fastest growing FinTech alongside a team of motivated and driven individuals CCPA Disclosure: Sezzle Inc. is committed to protecting the privacy of our job applicants. In compliance with the California Consumer Privacy Act (CCPA), we inform California residents about the personal information we may collect, the purposes for its collection, and your rights under the CCPA. For details about the categories of personal information we collect and your rights under the CCPA, please visit the California Office of the Attorney General's CCPA page. By submitting your application, you acknowledge that you have read and understood this CCPA disclosure. Equal Employment Opportunity: Sezzle Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, national origin, age, disability, genetic information, pregnancy, or any other legally protected status. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.  #Li-remote #full-time Pay Range $400,000—$600,000 USD

hi-logo [https://hi-contentful.imgix.net/4xN7JhmwCRuz3y9M8L8CF7/5c244c52cfc982bd1a348a80dc35d43b/hi-logo-new.svg?auto=format&ixlib=react-9.0.3&h=40&w=132&q=50&dpr=2] Human Interest is on a mission to ensure that people in all lines of work have access to retirement benefits.  More than half of all working Americans are not saving enough for their future. Too often, it’s because they are employed by a company that doesn’t offer a retirement plan. Human Interest is changing that by making it affordable and accessible for small and medium-sized businesses to offer employees a path to financial independence through retirement savings. We’re a high-growth fintech company changing the retirement industry. We are backed by a number of investors. This includes funding from Marshall Wace and Baillie Gifford, as well as top investors such as BlackRock [https://www.globenewswire.com/news-release/2023/01/13/2588448/0/en/Human-Interest-and-BlackRock-Join-Efforts-to-Expand-Access-to-Retirement-Plans-for-Working-Americans.html#:~:text=Human%20Interest%20has%20secured%20approximately%20%24500%20million%20in%20funding%20to%20date&text=NEW%20YORK%20and%20SAN%20FRANCISCO,businesses%20across%20the%20United%20States.], TPG (The Rise Fund) [https://www.globenewswire.com/news-release/2021/08/04/2274611/0/en/The-Rise-Fund-Leads-200M-Series-D-Investment-in-Human-Interest-to-Accelerate-Growth-and-Societal-Impact.html], SoftBank, Glynn Capital [https://www.globenewswire.com/news-release/2021/02/11/2174214/0/en/Human-Interest-Completes-105M-Series-C-Following-Breakout-Year-in-2020.html], NewView Capital, USVP, Wing, Uncork, and more. About the role As the Sales & Strategy Operations Director, you will report directly to the VP of Sales and work cross-functional with leaders to design, scale, and optimize the operational engine driving our sales and partner channels. Following our strategic realignment to focus RevOps on pure infrastructure and revenue efficiency, you will own the business systems strategy, data pipelines, and process design that empowers our field teams to convert and scale effortlessly. You are an expert at translating high-level revenue strategies into clean system architectures, eliminating friction for sales teams, and building bulletproof data tracking for executive visibility. What you get to do every day * Systems Architecture & Strategy: Own the architectural roadmap for our GTM tech stack (Salesforce, LeanData, Gong, and routing engines), ensuring it seamlessly scales with our multi-channel SMB and Mid-Market pipelines. * Process Engineering: Evaluate the end-to-end buyer and partner journeys to eliminate operational bottlenecks, automate manual handoffs, and maximize field productivity. * Data Integration & Insights: Partner with Data Engineering to maintain absolute data integrity across systems, ensuring that executive reporting (including QPR pipelines and conversion rates) accurately reflects realities. * Cross-Functional Collaboration: Serve as the strategic operational bridge between Sales, Partner Management, Finance, and the newly independent Marketing team to ensure seamless handoffs and pipeline clarity. * Change Management: Lead the rollout, documentation, and operational training of new system structures, tools, and workflows across the revenue organization. What you bring to the role * 8+ years of Sales or Revenue Operations experience, with a heavy concentration in B2B SaaS or high-growth FinTech environments. * Deep Salesforce Expertise: Proven track record designing, customizing, and scaling complex Salesforce instances, CPQ tools, and advanced lead-routing configurations. * Analytical Engine: Exceptional capacity for data analysis; experience turning raw pipeline metrics into actionable executive-level insights. * Execution & Drive: A track record of stepping into highly fluid, scaling environments and building structure, documentation, and standard operating procedures (SOPs) from the ground up. * Strategic Partnership: The ability to influence VP-level stakeholders, challenge assumptions constructively, and balance long-term system architecture with immediate business needs. Why you will love working at Human Interest Human Interest is tackling one of our country's biggest challenges - closing the retirement gap. You'll be instrumental in architecting and scaling solutions that bring financial security to employees at small and medium-sized businesses nationwide. We’ve made significant progress, but there is still growth ahead, offering you a unique opportunity to solve complex problems, drive innovation, and advance your career alongside a dedicated, mission-driven team. We value hard work and recognize that our team's contributions are key to our continued success. Join Human Interest and make a lasting impact by shaping the future of retirement. Our operating principles define how we work together as a team. They reflect Human Interest’s unique view on what’s important and what’s right. Documenting this core aspect of our culture helps employees make good decisions on their own. It also helps candidates considering career opportunities critically evaluate whether they will thrive at Human Interest.  * Customer obsession: We're all about creating amazing experiences for our customers. We put their needs first and go the extra mile to make them smile. * Long-Term Orientation: We're not just playing for today; we're building a legacy. We think big, plan strategically, and invest in our future. * Autonomous and Accountable Teams: We trust our team members to take ownership and make smart decisions. We empower you to be your best self! * An Escalating Bar for Talent and Performance: We're constantly raising the bar and challenging ourselves to be better. We believe in growth and continuous improvement. * Fundamental Optimism: We see the glass as half full (and then we fill it up with more amazing ideas!). We believe in the power of positivity and the potential for greatness. Compensation - At Human Interest, there are a number of factors that are used to determine the appropriate pay range for each position. We take into account the cost of labor for each position in various markets across the U.S. The base salary for this position spans $170,000 - $175,000 and represents the minimum in our lowest geographic region to a maximum in our highest geographic region. The salary we offer to a new employee within this range is based on their location within the U.S., their relevant job-related skills, and experience. At Human Interest, base salary is one component of the overall total rewards package. Depending on the position, additional compensation components such as bonuses, commissions, and equity may be offered. All of our employees are offered a robust suite of physical, financial, and mental wellness benefits. In compliance with applicable laws, we do not inquire about salary history, or about criminal history prior to a conditional offer of employment. Benefits -  * A great 401(k) plan: Our own! Our 401(k) includes a dollar-for-dollar employer match up to 4% of compensation (immediately vested) and $0 plan fees * Top-of-the-line health plans, as well as dental and vision insurance * Competitive time off and parental leave * Addition Wealth:  Unlimited access to digital tools, financial professionals, and a knowledge center to help you understand your equity and support your financial wellness * Lyra: Enhanced Mental Health Support for Employees and dependents   * Carrot: Fertility healthcare and family forming benefits * Candidly:  Student loan resource to help you and your family plan, borrow, and repay student debt * Monthly work-from-home stipend; quarterly lifestyle stipend * Engaging team-building experiences, ranging from virtual social events to team offsites, promoting collaboration and camaraderie. We’re a great place to work (but don’t take our word for it)  Here’s a list of our awards and accolades: * Certified as a Great Place To Work® (2023-2025) * Fortune Best Place to Work in the Bay Area (2024) * Best Places to Work by Built In (2023-2024) * America’s Best Startup Employers by Forbes (2020-2022, 2024)  * A Top Company by Y Combinator (2020-2023) * Inc. Fastest Growing Companies (2021) Human Interest is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, sex, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran or military status, pregnancy, or any other characteristics protected under federal, state, or local laws. Employment with Human Interest is at-will, meaning either you or the company may terminate employment at any time, with or without cause or notice, except as otherwise provided by law or written agreement. We are committed to making every stage of our application process fully accessible to all individuals. If you need a reasonable accommodation at any point in the process, please let us know at applicantaccommodations@humaninterest.com [applicantaccommodations@humaninterest.com]. Protect yourself against fraud and identity theft. Apply to our open positions directly via our careers page [https://job-boards.greenhouse.io/humaninterest] on Greenhouse. Human Interest will never ask applicants for their financial or banking information as part of our application process. All legitimate communication will come from a @humaninterest.com [http://humaninterest.com] email address. If you have questions, please reach out to us directly at careers@humaninterest.com Please note Human Interest does not accept unsolicited resumes from any source other than directly from candidates. We will not consider resumes from vendors, including and without limitation search firms, staffing agencies, fee-based referral services, and recruiting agencies.  Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment-qualified applicants with arrest and conviction records. We comply with CCPA [https://humaninterest.com/applicant-privacy-notice/] guidelines. See more: https://humaninterest.com/disclosures [https://humaninterest.com/disclosures]