AI engineer II (Remote)

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 AI Engineer II who is best in class, with a high IQ and a high EQ. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team, with strong prospects for continued growth and increased ownership.

As an AI Engineer II on the Applied AI team, you will take on end-to-end ownership of complex platforms and systems that power Sezzle's AI-driven capabilities. Your work will span initiatives such as building AI-powered platforms from scratch, developing intelligent automation and orchestration systems, and embedding proprietary AI solutions directly into customer-facing products, internal tools, and operational workflows.

You will operate in highly ambiguous problem spaces, working closely with product, engineering, and operations teams to identify opportunities where AI can drive meaningful impact — whether that's enhancing the customer experience, improving decision-making, or automating complex workflows. This role is ideal for engineers ready to move beyond scoped execution and into leading solutions: shaping architecture, driving implementation, and ensuring that what is built is reliable, scalable, and genuinely useful for both external users and internal teams.

What You'll Do:

• Lead the design, development, and ownership of AI-powered internal platforms and systems, including initiatives built from the ground up.
• Own end-to-end delivery of complex projects, from problem discovery and system design through production rollout and iteration.
• Design and implement AI-driven features, intelligent automation, and orchestration systems that enhance customer experiences and compound productivity across teams.
• Embed AI capabilities into customer-facing products, internal tools, and operational workflows, ensuring solutions integrate naturally and deliver measurable value.
• Build full-stack systems spanning backend services, APIs, data layers, and frontend interfaces.
• Translate ambiguous business and operational problems into scalable, maintainable, AI-enabled technical solutions.
• Apply strong systems thinking to ensure reliability, performance, security, permissions, and auditability across platforms.
• Collaborate closely with engineers, teams, and stakeholders across the company to identify high-impact opportunities and drive adoption.
• Participate in production support and incident response for owned systems, helping define and uphold reliability and operational best practices.
• Mentor AI team members through code reviews, design feedback, and hands-on guidance, raising the overall quality bar of the team.

What We Look for:

• 3–5 years of professional experience in software engineering, AI engineering, platform engineering, or related roles.
• Hands-on experience designing, building, and shipping AI-powered systems into production environments.
• Strong proficiency in Python, SQL, and frontend frameworks such as React.
• Proven experience designing and owning production-grade full-stack systems.
• Experience working with distributed systems, internal platforms, or complex data workflows.
• Ability to operate effectively in ambiguous problem spaces and drive solutions with minimal direction.

Preferred Qualifications:

• Experience building AI-first platforms or internal products from scratch, including early architectural decisions.
• Strong foundation in core machine learning and data science principles, including supervised/unsupervised learning, feature engineering, model evaluation, and statistical inference.
• Experience with transformer architectures (BERT, GPT, etc.) and understanding of attention mechanisms, tokenization, and fine-tuning strategies for domain-specific applications.
• Experience developing AI-assisted or agentic systems that interact with tools, data, or workflows.
• Familiarity with embeddings and vector representations, including text embeddings, similarity search, and integration with vector databases (Pinecone, Weaviate, pgvector, or similar).
• Experience with NLP techniques including text classification, named entity recognition, semantic search, and information extraction.
• Familiarity with cloud-native development using AWS.
• Understanding of prompt engineering, retrieval-augmented generation (RAG), and LLM application patterns.
• Experience with containerized systems and orchestration tools such as Docker and Kubernetes.
• Exposure to CI/CD pipelines and modern development workflows (e.g., GitLab).
• Experience with Golang is a plus (or willingness to learn).

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.

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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