Senior Payroll Specialist, Colombia

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 a talented and motivated Senior Payroll Specialist for Colombia who is best in class with a high IQ plus a high EQ. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team, with abundant prospects for career advancement. Sezzle is standing up its own Colombian operating entity (Sezzle Colombia SAS) and bringing its Colombian team in-house. Payroll execution will sit with a specialist BPO partner; you will be the Sezzle-side owner of the relationship and the last line of defense before any payment is released. The first Sezzle Colombia payroll cycle goes live on 31 October 2026 with approximately 130 team members in scope, and you will be central to making sure it lands clean, compliant, and on time. This is a build phase, not a steady-state operations role: you will write the playbook for how Sezzle runs Colombian payroll. You will report to Sezzle's Payroll Manager and work in close partnership with the Compensation & Benefits, Finance, and Legal functions, as well as the new Colombian operating leadership. What You'll Do: Own the end-to-end monthly Colombian payroll cycle in partnership with the BPO payroll provider: data submission, validation, reconciliation, approval, payment release, post-cycle review, SLA management, escalation handling, and deadline accountability Be the single point of accountability on the Sezzle side for accuracy of every payroll run. Catch BPO errors before they leave the building. Manage the data interface between Sezzle's HRIS (UKG), the BPO, and Finance: new hires, terminations, compensation changes, bonuses, leaves, vacation accruals, deductions. Ensure full Colombian statutory compliance month after month: aportes parafiscales, EPS, ARL, AFP, cesantías, intereses sobre cesantías, prima de servicios, vacaciones, retención en la fuente. Own the year-end and mid-year statutory cycles: certificación de ingresos y retenciones, prima de junio y diciembre, vacation true-ups, end-of-year reconciliation. Coordinate treasury funding with Finance, prepare journal entries and accruals, and partner on monthly close. Be the first point of escalation for any Colombian team member's payroll inquiry. Resolve, document, and feed back into process improvements. Partner with Legal and Compliance on Colombian labor reform changes (which are frequent), and translate them into operational payroll changes without missing a cycle. Build and maintain audit-ready SOPs, payroll calendars, control matrices, and exception logs from day one. This is greenfield: there is no inherited playbook. Support the Remoti-to-Sezzle Colombia SAS payroll transition through 1 October 2026 cutover, including initial roster build-out in UKG, BPO onboarding handshake, parallel-run validation, and first-cycle dress rehearsal. Manage the Payoneer / cross-border payment mechanics for any USD-denominated contractor payments that remain outside the Sezzle Colombia SAS payroll perimeter. Oversee Unidad de Gestión Pensional y Parafiscales (UGPP) audits What We Look For: 5+ years of hands-on Colombian payroll experience, with the majority in technology, fintech, marketplace, or SaaS environments. Bachelor's degree in Finance or in a related field. Deep, current expertise in Colombian labor law, payroll statutory requirements including PILA submission experience, DIAN reporting, and the practical operational details of cesantías, prima, parafiscales, and the social security system. Demonstrated experience as the client-side coordinator with an outsourced/BPO payroll provider. You know how to manage a BPO, not just be one. Experience running payroll for small-to-mid Colombian teams (50–250 people) for a global parent company. You have lived the cross-border data + cross-time-zone coordination problem. Advanced proficiency in Excel or Google Sheets for payroll reconciliation, variance analysis, and error detection. Strong working English. You will communicate daily with US-based People Ops, Finance, and Legal stakeholders. HRIS experience (UKG, Workday, ADP, or similar). You are comfortable with HRIS-to-payroll data flows, not just spreadsheet payroll. A documented track record of catching errors before they ship — comfortable saying "hold the payment, I need 20 minutes" and meaning it. Discretion appropriate to the data you will handle: total compensation, terminations, sensitive personal information. Demonstrated experience working with Claude or equivalent large language model tools is required; candidates must be comfortable leveraging AI to enhance productivity, research, and communication. Preferred Qualifications Experience leading a payroll transition or BPO implementation: provider change, entity standup, EOR exit, or a company-wide HRIS migration. Familiarity with Payoneer or other USD-denominated contractor payment rails. Practical experience operating across both empleado dependiente and contratista independiente populations under one roof, and the labor-risk implications of each. Background in a publicly listed or pre-IPO fintech, with familiarity with SOX-adjacent controls and external-audit readiness. Spanish (native) + English (fluent business). 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. 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 believe in surrounding ourselves with only the best and the brightest individuals. 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. #Li-remote #Full-time