Manager, Tier 2 Support

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 Manager, Tier 2 Support who is best in class with a high IQ plus a high EQ. You will lead Sezzle's Tier 2 (T2) Support team, the escalation layer that investigates and resolves the shopper issues frontline Support cannot: account access and identity verification, payment method and multiple-charge investigations, Payment Streaks tier reinstatements, and Sezzle Send reversals. This role reports to the Director of Insights in the Customer Experience department.

You will be accountable for three things: fast, accurate resolution of every escalation; T2 decisions that are documented and defensible to auditors, regulators, and our bank partner; and fewer escalations over time, achieved by finding root causes and getting them fixed with Product, Risk, Payments, and Trust & Safety. This role sits in a fast-paced, rapidly growing team with abundant prospects for career advancement.

What You'll Do: 

• Lead, hire, coach, and develop the T2 Operations team; set schedules and coverage so escalations are worked within SLA.
• Own the T2 escalation queue end to end: intake standards from frontline, triage, prioritization, and the routing paths to Risk, Payments, Trust & Safety, and other escalation teams.
• Own T2's operating procedures and keep every SOP current, consistent, and audit-ready.
• Make sure T2 work meets consumer-protection obligations: recognizing when an investigation needs to be rerouted for proper handling, no disclosure of other shoppers' account details, and strict PII handling in tickets, Slack, and AI tools.
• Find patterns in escalation volume and drive fixes with Product, Engineering, and Payments; file and track defects until they are resolved.
• Provide feedback to support training and managers to enhance agent knowledge and avoid future mis-escalations
• Report weekly and monthly on T2 volume, resolution time, escalation drivers, and quality, and support complaint, audit, and regulatory responses with case-level evidence.  

What We Look For: 

• 3+ years in a people-leadership role (manager, supervisor, or team lead with direct reports) in a customer support or operations environment.
• 3+ years in technical support or escalations at a fintech company, such as payments, BNPL, lending, banking, or cards.
• Familiarity with payment rails (ACH, card networks, wire transfers), ledger systems, API integrations, and webhook monitoring.
• Hands-on experience investigating account, payment, and transaction issues in internal admin tools and a ticketing platform (Zendesk or similar).
• Working knowledge of consumer-financial regulations that affect support, such as Reg E, Reg Z/TILA, FCRA, and UDAAP.
• 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 with BNPL or installment-lending products, virtual cards, or P2P money movement.
• Comfort with SQL or self-serve data tools to pull account and transaction data for investigations.
• Experience with fraud, account-takeover, and identity-verification workflows.
• A record of writing SOPs and knowledge-base content that frontline teams actually use.
• Experience supporting regulatory exams, bank-partner audits, or complaint responses (CFPB, state AGs, BBB).
• Clear, calm communicator who can explain technical root causes to agents, partners, and leadership.

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. 

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