Staff PRODUCT ENGINEER (Contract)

Build it. Ship it. Own it.

Location: Argentina, Brazil, Colombia, Chile, Mexico, Dominican Republic, Peru

About Counterpart

Counterpart is an insurtech platform reimagining management and professional liability for the modern workplace. We believe that when businesses lead with clarity and confidence, they become more resilient, more innovative, and better prepared for what's ahead. That's why we built the first Agentic Insurance™ system — where advanced AI and deep insurance expertise come together to proactively assess, mitigate, and manage risk. Backed by A-rated carriers and trusted by brokers nationwide, our platform helps small businesses grow with confidence. Join us in shaping a smarter future, helping businesses Do More With Less Risk®.

The Role

As a Product Engineer at Counterpart, you own problems and drive outcomes. You iron out requirements with stakeholders, partners, and customers. You leverage AI for implementation. You verify the end-to-end result. You iterate until you move the needle.

You run projects with other Product Engineers and AI agents. You know when to delegate to a human, when to delegate to an agent, and when to do it yourself. 

YOU WILL

Own the Problem

• Take accountability for the outcome. 
• Talk directly to your users, stakeholders, and peers to discover the problem. 
• Translate business intents into functional requirements that engineers and agents can build against. Determine where human judgment is non-negotiable and where AI can augment or act autonomously. 
• Own the non-functional technical requirements. Specify the quality bar: performance, scalability, reliability, security, maintainability.

Build with AI

• Write production-quality code across the stack: Python, Django, AWS, React, and PostgreSQL. You are not afraid of any layer.
• Direct agents and review their output with domain depth. Catch what they miss across the functional and non-functional bar: correctness, edge cases, performance, security, testability, readability.
• Evaluate and improve agent output regularly. Track failure modes. Refine the prompts and patterns that lift the quality ceiling over time.
• Run projects that span other Product Engineers and agents. Coordinate work, manage dependencies, and keep things moving without micromanaging.
• Contribute to architectural decisions. Bring options and alternatives, not objections. Know when the elegant solution is the wrong call for a startup moving fast.
• Contribute to and manage the context harness as you build and deliver.

Verify and Iterate

• Surface delivery risks early. Bring solutions, not just problems. Keep your stakeholders informed without turning every risk into a meeting.
• Verify the end-to-end result yourself. Confirm the system does what the requirements say, and that the requirements were right.
• Drive adoption of what you ship. Documentation, enablement, and usage monitoring are part of the job.
• Monitor your services in production. Own the signal. Debug and fix what breaks.
• Participate in support rotations. When users run into issues with what you shipped, you investigate and fix them.
• Iterate until you move the needle. Shipping is not the finish line. Outcome is.

Raise the Bar

• Mentor engineers around you. Give direct, useful feedback. Leave things better than you found them.
• Make deliberate calls on technical debt: when to accumulate it, when to pay it down, when to refactor. Translate trade-offs into language that business leaders can act on.
• Operate to the engineering standards for quality, reliability, and operational excellence.

YOU HAVE

• 10+ years building production web applications across the full stack. The years are the floor, not the bar. What matters is whether you have actually done this: owned a problem end-to-end, written the spec, built the thing, coordinated the work, and shipped it without someone else holding the thread.
• Demonstrated experience gathering requirements directly. You have interviewed users, customers, and partner teams, and turned ambiguous intent into specs that engineers and agents can build against.
• Demonstrated experience owning both functional and non-functional requirements. You have defined what a system must do and held the line on how well it must do it.
• A track record of owning a domain or initiative without close supervision. You have navigated ambiguity, made judgment calls, and been accountable for the outcome.
• Extreme ownership and a bias for action. You do not sit and wait. You chase stakeholders, customers, and answers when you need them.
• Experience coordinating across engineers and AI agents on a shared initiative. You have managed the work without holding a formal management title.
• Strong technical judgment and the depth to catch what AI-generated code gets wrong: not syntax, but correctness, architecture, intent.
• Proficiency with Python and Django. Working knowledge of TypeScript, React, and PostgreSQL.
• Proficiency in developing with AI tools (Claude Code, Cursor, OpenAI Codex, similar) and the drive to stay ahead of how AI development practices are evolving.
• Domain curiosity. You learn the business context your work supports, not just the systems. You understand why the problem matters, not just how to solve it.
• The ability to communicate clearly across engineering, product, and business, translating technical complexity without losing meaning.
• Low ego and high Emotional Quotient (EQ). You influence without authority, take feedback well, and leave your ego out of technical decisions.
• Experience working with distributed, remote teams.

HOW THIS ROLE WORKS

Product Engineering exists to collapse the distance between a problem and a working solution. You own a problem or part of a vision. You shape it with stakeholders. You build it with AI. You verify it end-to-end. You iterate until the metric moves.

You work within the Context Architecture, a shared system of documentation, design patterns, and domain knowledge that gives you the technical context to make autonomous decisions at every step.

This is not a role for engineers who need to be told how. It is a role for engineers who can take a problem, fill in the gaps with good judgment, and ship something that works.

WHO YOU WILL WORK WITH

• Derrick Franco, Principal Engineer: After teaching himself to code at 13, Derrick went on to co-found Jumpstart in addition to building out the technical divisions at InvestorsAlley and Phinaz Media Group. Nowadays Derrick spends his time reading, with his wife, and working on his podcast The Future of Work Project.
• Julian Prokay, Principal Engineer: A veteran of the SaaS space with experience working on both student systems and construction management software. In his free time, he enjoys history podcasts and fantasy literature.
• Tony Nguyen, Engineering Manager: Tony is an engineering and platform leader with 25+ years of leadership experience at companies like Sony PlayStation Network, Intuit TurboTax, and ServiceNow. He thrives at building products, scaling teams, and leading organizations, but more so building people. He believes the best leadership and engineering comes from bringing your full identity to work. For him that's faith, family, and sports! Outside of work, you can catch him on the couch with his 3 adult children watching anime, going to Disneyland, or having game nights.
• Ron Alexessen, Engineering Manager: With experience at Hewlett-Packard, New Relic, Rackspace, and consulting agencies, Ron has built teams and shaped technical culture across different environments. He's passionate about AI-enabled development as a force multiplier and building solutions that create real business impact. Outside work, he boulders, runs, rides gravel bikes, and co-parents active teenagers, embracing structured chaos in all of it.
• Newton Truong, Engineering Manager: Newton joins Counterpart with 7+ years of experience in platform and data engineering. In his last company Thrive Market, he had a hand in building out new microservices and architecting data pipelines with Airflow and Spark. He's vegetarian and loves trying new restaurants when traveling. Nowadays he's busy keeping up with his 2-year-old and doing outdoor activities with his family.
• John Mendez, Engineering Manager: John has experience working at companies of all sizes. He enjoys startups and small-to-medium businesses, where he can wear multiple hats and help deliver solutions. Outside of work, he stays busy with his four kids and their activities. He also makes time to stay active by working out at home and running or walking with his dog.

COUNTERPART'S VALUES

• Conjoin Expectations - it is the cornerstone of autonomy. Ensure you are aware of what is expected of you and clearly articulate what you expect of others.
• Speak Boldly & Honestly - the only failure is not learning from mistakes. Don't cheat yourself and your colleagues of the feedback needed when expectations aren't being met.
• Be Entrepreneurial - control your own destiny. Embrace action over perfection while navigating any obstacles that stand in the way of your ultimate goal. Leverage AI ruthlessly. We measure success by outcomes, not lines of code written. Use every available AI tool to ship faster and think more strategically.
• Practice Omotenashi ("selfless hospitality") - trust will follow. Consider every interaction with internal and external partners an opportunity to develop trust by going above and beyond what is expected.
• Hold Nothing As Sacred - create routines but modify them routinely. Take the time to reflect on where the business is today, where it needs to go, and what you have to change in order to get there.
• Prioritize Wellness - some things should never be sacrificed. We create an environment that stretches everyone to grow and improve, which is fulfilling, but is only one part of a meaningful life.

WE OFFER

1. Work from Anywhere - Counterpart is a fully distributed company, meaning there is no office. We allow employees to work from wherever they do their best work, of course prioritizing meetings that often happen in US time zones.
2. Language Classes - We sponsor up to $100 per calendar year to be used towards language classes to help support your English language skills.
3. Paid Vacation and Time Off
4. Parental Leave - Development Partners will be eligible for unpaid Parental Leave to bond with a newborn, newly-adopted, or newly placed child. Under this policy, development partners and independent contractors will be eligible for up to 8 weeks of unpaid parental leave. Any time off will be subject to approval and must be requested at least 45 days in advance.
5. Computer - We reimburse you for your locally procured MacBook Pro. If you are still with the company after one year, it is yours to keep!

Our estimated pay range for this role is USD $90,000 - $110,000 annually. Contractor compensation is determined by a variety of factors, including but not limited to, market data, location, internal equitability, and experience.

We are committed to being a welcoming and inclusive workplace for everyone, and we are intentional about making sure people feel respected, supported and connected at work, regardless of who you are or where you come from. We value and celebrate our differences and we believe being open about who we are allows us to do the best work of our lives.

We are an Equal Opportunity Employer. We do not discriminate against qualified applicants or employees on the basis of race, color, religion, gender identity, sex, sexual preference, sexual identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, mental disability, medical condition, military status, or any other characteristic protected by federal, state, or local law, rule, or regulation.

The Role:

As a Principal Software Engineer on the Cyberbank Core team at Galileo, you will lead broad, impactful projects across multiple teams as one of the senior-most technical contributors shaping our next-generation lean core banking platform. Your influence will span teams, projects, and geographies, driving both technical direction and how our teams design, build, and operate the services and data pipelines that power scalable, performant, and secure banking products.

You will be hands-on and in the details as an exemplary practitioner: in the software we develop, in the infrastructure we operate, and in the tools and techniques we use to test, release, and maintain it at scale. You will help teams evolve codebases to ship improvements safely and frequently in a regulated, cloud-native environment. As part of this, you will steward a broader engineering community and mentor engineers across the organization.

You will proactively identify the right problems to solve and advocate for organizational priorities. This role is inherently cross-functional, you will work closely with engineering, product, compliance, data, and executive stakeholders to define and execute on technical strategy for Cyberbank Core. You'll face and solve a wide range of challenges: architectural, operational, and product-related, across multiple products and geographies.

What You’ll Do:

• Own driving Cyberbank Core's software architecture and systems forward — setting long-term direction and executing on it across multiple teams and quarters, with a particular focus on the core banking services, data pipelines, and API platform.
• Build as an exemplary practitioner: get hands-on developing software and set a high quality standard for teams to follow.
• Define the right boundaries, APIs, and integrations between teams and with clients and partners to ensure technical and business success across multiple geographies.
• Solve complex engineering problems endemic to high-availability, low-latency, scalable distributed systems in a regulated banking environment.
• Execute large-scale projects — leading design, planning, and execution across multiple teams to drive technical direction and product outcomes.
• Drive the design and implementation of scalable, secure, and highly available SaaS services and data engineering pipelines that support next-generation core banking capabilities.
• Proactively identify broader problems and opportunities. Anticipate and design the next generation of our systems and products.
• Raise the quality of our engineering teams: identify opportunities and advocate for improvements to how we write software, our approach to testing and quality, and the habits and processes of highly effective teams.
• Mentor and coach individuals and teams across the company. Steward engineering communities, fostering design collaboration and mindshare.
• Articulate how technical architecture and team structure interact, and provide input on the right organizational structure to deliver on our engineering goals.
• Serve as a strategic advisor to leadership, representing technical strategy to business and executive stakeholders and participating in strategic planning.
• Continuously drive improvement, new practices, and operational excellence initiatives across the department.
• Champion improvements in code, design, and operational reviews. Lead initiatives that improve department software quality and operations. Be a stakeholder in engineering norms and standards for code quality, software quality, and operational excellence.

What You’ll Need:

• 10+ years of programming experience; mastery of software development independent of language.
• Advanced expertise in designing, building, and operating large-scale fault-tolerant distributed systems, applications, databases, and workflows.
• Demonstrated experience with continuous delivery principles and techniques: you've built systems with layered test automation that is always safe for automated releases to production, enabling a great, low-cycle-time developer experience.
• Deep expertise in designing and managing cloud-based solutions with a strong focus on resiliency experience with AWS (or other public cloud infrastructure) required.
• A high standard for what "great" looks like, and experience continuously improving legacy systems to reach it.
• Strong judgment, and experience recognizing and driving out critical decisions in a balanced and pragmatic way.
• Excellent verbal and written communication skills with the ability to influence and collaborate effectively across remote, distributed teams.
• Experience working in a regulated industry.
• Experience working on banking backends, particularly cores, ledgers, or payment systems is a plus.
• Bi-lingual Spanish/English required.

The salary range for this role is $6,000 - $12,500 per month (Gross in USD) 

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!

Compensation:

For this principal development role, with 12+ years of experience, the compensation range is  $6,000 - $12,500 per month. This range acknowledges the extensive expertise, leadership capabilities, and significant contributions expected at this level, offering a competitive salary to reflect the value of advanced skills and experience.

Interview Process

We believe transparency is important at Sezzle. Regularly providing feedback while setting expectations is part of our culture starting with the interview process. Advancement through each step is not guaranteed.

• Application submitted (you are here)
• Wonderlic test (30-40 min)
• Interview with recruiters (30 min)
• Coding assessment (~1.5 hours)
• Interview with engineers (1 hour)
• Interview with engineering leadership (30-45 min)
• Offer!

About the Role: 

We are seeking a talented and motivated best-in-class Principal Software Engineer. 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.

As a Principal Software Engineer with Sezzle, you will work with highly-motivated teams to tackle interesting and challenging problems across multiple areas of the organization. Your experience and guidance will help other members of the team level-up their own skills as well. You will spend your time working with AI/ML tooling to identify creative uses to fill existing and emerging gaps in the applications.

In this backend focused role, you will work closely with stakeholders from Product, Support and the business. You’ll also partner with other engineering teams to provide high-quality, scalable, and innovative solutions to internal and customer problems. Your day-to-day responsibilities will include designing, developing, and delivering new features, as well as unblocking and mentoring your teammates. Your work will generally focus on the lower level features and optimizations.

This role has both an internal and external focus, your contributions will make a meaningful difference in the day-to-day lives of your peers at Sezzle, enhancing their ability to support our business and customers, and you will have opportunities to take any feedback and iterate.

What You'll Do:

• Architect, design, and build scalable backend services and APIs primarily in Golang, leveraging AWS, RDS (MySQL/Postgres), and modern distributed patterns.
• Lead Sezzle’s AI enablement efforts, identifying opportunities to apply AI and automation to enhance developer productivity, internal tooling, and customer experiences.
• Partner with teams across the organization to integrate modern AI capabilities - Primarily around tools like Claude Code, Codex, Cursor and enhancing team productivity.
• Drive consistency and scalability across a distributed microservices architecture while maintaining performance and reliability.
• Establish and evolve engineering best practices for observability, security, and CI/CD across teams.
• Mentor engineers and champion a culture of learning, innovation, and operational excellence.
• Collaborate cross-functionally to translate business goals into technical roadmaps and deliver results that matter.

What We Look For:

• 12+ years of professional software engineering experience, including significant backend experience.
• Deployed significant changes to a production application in the past 30 days.
• Strong proficiency in Golang, with experience building and maintaining RESTful APIs.
• Expertise with SQL-based RDBMS (MySQL, PostgreSQL) and experience optimizing schema and queries for performance at scale.
• Solid understanding of distributed systems design patterns (e.g., transactional outbox, event-driven architecture, queues).
• Demonstrated ability to bring new ideas forward, influence decisions, and lead complex technical initiatives.
• Bachelor’s degree in Computer Science or equivalent practical experience.

Preferred Knowledge and Skills:

• Proficiency in observability tools (Prometheus, Grafana, Datadog, New Relic).
• Experience with AWS cloud infrastructure, mainly AWS Aurora RDS, both MySQL and Postgres.
• Experience in fintech, payments, BNPL, or consumer lending - familiarity with financial compliance, credit decisioning, or transaction processing systems.
• Experience with CI/CD pipelines and containerized microservices (Docker, Kubernetes).
• Working knowledge of TypeScript, React, or React Native.
• Familiarity with AI/ML tooling (e.g., OpenAI API, LangChain, Hugging Face, or custom LLM integrations).
• Track record of shipping commercial APIs and data-driven applications in high-growth environments.
• Proven leadership in guiding technical direction, improving system reliability, and scaling engineering organizations.

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, Elasticsearch
• 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.

#Li-remote #full-time

The salary range for this role is $5,000 - $9,500 per month (Gross in USD)

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!

Compensation:

For this principal development role, with 6+ years of experience, the compensation range is $5,000 - $9,500 USD based on experience level per month and in gross amount. This range acknowledges the extensive expertise, leadership capabilities, and significant contributions expected at this level, offering a competitive salary to reflect the value of advanced skills and experience

About the Role: 

We are seeking a hands-on, high-impact Senior Security Infrastructure Engineer to help strengthen Sezzle’s security posture across cloud infrastructure, applications, and developer workflows. This role is ideal for someone who thrives in a fast-paced environment and wants to work on real-world security problems at scale.

As a Senior Security Infrastructure Engineer, you will have a high degree of ownership and autonomy to identify risks, investigate issues, and drive meaningful security improvements across our systems. You will work across vulnerability management, detection engineering, supply chain security, and incident response - partnering closely with engineering teams to ensure security is practical, effective, and embedded into how we build and operate systems. You should consider yourself a DOer - someone who is comfortable diving into logs, analyzing systems, validating findings, and working end-to-end to get issues resolved. We value engineers who bring strong technical depth, good judgment, and the ability to turn security insights into actionable outcomes.

This role offers the opportunity to shape and scale security capabilities, including detection systems, supply chain risk controls, and security automation. With the support of modern tooling (including AI where appropriate), you will play a key role in improving efficiency, visibility, and resilience across the organization. This role combines hands-on security operations with exploratory and design work. You will spend significant time investigating and resolving real-world issues, while also researching, evaluating, and building new security capabilities across areas like detection, supply chain security, and data protection.

What You’ll Do: 

• Lead and operate vulnerability management across infrastructure, platforms, and applications - including internal scans, dependency analysis, and external findings, validating true positives and driving remediation with engineering teams
• Build, operate, and mature SIEM/XDR capabilities, including log ingestion, detection rule development, alert tuning, and investigation workflows
• Investigate and respond to security incidents across cloud infrastructure and applications, performing root cause analysis and driving long-term fixes
• Design and implement detection strategies for suspicious activity, including data exfiltration patterns using application and database telemetry
• Lead and contribute to threat modeling exercises and security design reviews to identify risks early and strengthen architecture
• Apply deep expertise in AWS and Kubernetes to design, secure, and improve resilient and secure cloud infrastructure at scale
• Drive infrastructure and CI/CD hardening initiatives, with a focus on reducing software and container supply chain risk
• Lead efforts to implement and improve dependency and container supply chain risk detection systems and controls
• Partner closely with engineering teams to remediate vulnerabilities and improve secure development and deployment practices
• Support and implement security controls aligned with PCI DSS, SOC 2, and other compliance requirements
• Develop and implement automation (including AI where appropriate) to improve efficiency in security operations, detection, and response
• Triage and validate external security findings, distinguishing true positives and coordinating remediation

What We Look For: 

• 6+ years of experience in security, software, or infrastructure engineering, with hands-on experience securing cloud-based production systems and working with real-world security challenges
• Experience contributing to threat modeling and security design reviews for modern systems
• Strong hands-on experience in vulnerability management, including scanning, triage, validation, remediation coordination, and verification
• Experience working with SIEM platforms (e.g., Wazuh, Splunk, ELK) for detection engineering, monitoring, and incident response
• Practical experience triaging findings from vulnerability scanners and bug bounty programs
• Strong knowledge of AWS, Linux, and Kubernetes infrastructure, including security architecture, hardening, and operational best practices
• Experience improving infrastructure security, including CI/CD hardening and mitigating software supply chain risks
• Experience with container and dependency security tools (e.g., Snyk, Trivy, Grype, etc.)
• Ability to investigate issues directly using logs, cloud tooling, and system-level data
• Knowledge of common security vulnerabilities and mitigation strategies (OWASP, SANS, etc.)
• Working knowledge of compliance frameworks such as PCI DSS and SOC 2

Preferred Knowledge and Skills:

• Experience designing and tuning detection rules, reducing alert noise, and improving investigation workflows
• Strong understanding of cloud-native security controls, including IAM, network segmentation, and container security
• Familiarity with log-based detection, telemetry pipelines, and security analytics use cases
• Experience designing secure CI/CD workflows that reduce exposure to vulnerable dependencies and untrusted artifacts
• Ability to assess application and infrastructure risk and translate findings into actionable improvements
• Experience aligning technical security work with regulatory and compliance expectations
• Experience using automation and AI to reduce manual effort and improve consistency at scale

About You: 

• You think proactively about security and work to address risk early through clear design feedback and practical engineering solutions
• You bring strong cloud and infrastructure judgment, especially in AWS and Kubernetes environments
• You raise the bar on hardening and operational discipline, especially in CI/CD and supply chain security practices
• You approach security monitoring with an investigator’s mindset and can turn telemetry into meaningful detection and response outcomes
• You are excited to use automation and emerging technologies (including AI) to automate repetitive security work and improve team effectiveness
• You balance strong security standards with business needs and can support privacy and compliance requirements in a practical, scalable way
• 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, Elasticsearch
• 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.

#Li-remote #full-time

The salary range for this role is negotiable, the range being $6,000-$12,500 per month (Gross in USD), based on location and experience level.  

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!

Compensation:

For this principal development role, with 12+ years of experience, the compensation range is  $6,000 - $12,500 USD based on location and experience level per month and in gross amount. This range acknowledges the extensive expertise, leadership capabilities, and significant contributions expected at this level, offering a competitive salary to reflect the value of advanced skills and experience

About the Role: 

We are seeking a talented and motivated, best-in-class Principal Engineer for our Data Infrastructure. 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 growing; our data generation and consumption is growing with us at an increasing scale. Data is extremely valuable, and we want to empower the business, the engineers, and the rest of the organization to be able to read, write, and analyze large volumes of it quickly and efficiently.

Sezzle is a heavy consumer of MySQL, Postgres, and Redshift, leveraging AWS tooling with Aurora RDS and DMS. We use DBT-based transformations and similar toolkits to populate a rapidly growing data lake that supports multiple data warehouses. It’s scaled well with us so far, and we’re looking to continue improving it, but we also want to step into new tooling and technologies.

What you’ll do: 

• End to end ownership of our database and data warehousing infrastructure, its KPIs and its SLAs, including MySQL, Postgres, CDC capture, and Redshift.
• Lead optimizations in database and query performance.
• ​​Build and maintain tooling to help manage and upgrade our data infrastructure, continually improving with migrations and optimizations.
• Partner with Development to ensure we ship solid queries against a battle-tested schema to meet the needs of our products and business.

• Help Sezzle evolve our data systems beyond the current scale and stack with whatever tooling is necessary to handle processing high volumes of writes and events while performing complex ETL.
• Evaluate and integrate new technologies, guiding the evolution of Sezzle’s data infrastructure.
• Help data engineers and analysts optimize Redshift and warehouse performance, including query tuning, modeling improvements, and cost management.

What We look for: 

• 12+ years of experience in DBA, SRE, or Data Engineering roles, with a strong track record of scaling production-grade systems.
• Deep expertise with MySQL, Postgres, AWS Redshift or similar products, including performance tuning, table design, and workload management.
• Advanced proficiency in SQL.
• Strong hands-on experience with data replication and ETL/ELT frameworks, especially DBT, AWS DMS, or similar tools.
• Strong understanding of data modeling, distributed systems, and warehouse/lake design patterns.
• Ability to work in a fast-paced, collaborative environment with excellent communication and documentation skills.

Preferred Knowledge and Skills:

• Prior experience in high-growth, data-intensive fintech or similar regulated environments.
• Knowledge of lakehouse architectures and modern stacks such as Snowflake, Databricks, Iceberg, or Delta Lake.
• Some background in designing scalable, fault-tolerant data pipelines using modern orchestration tools (Airflow, Dagster, Prefect, etc.) processing anywhere from 100GB to 1 TB of new data a day
• Familiarity with streaming technologies (Kafka, Kinesis, Flink, Spark Streaming).
• High enthusiasm for using AI to be as productive as possible.

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, Elasticsearch
• 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.

#Li-remote #full-time

The Opportunity

This is a senior technical client leadership role that blends deep hands-on ML expertise with strategic advisory and consulting skills. You will be the most experienced ML voice across a diverse and expanding book of customer engagements — from early-stage companies bringing ambitious ML ideas to market, to established enterprises modernizing how they build and operate AI systems on AWS.

You will shape strategy, influence architecture, and leave every team you touch better than you found it. You bring the scientific depth to design and evaluate models rigorously, the engineering depth to architect production ML systems at scale, and the consulting instincts to translate both into business value for customers.

If you have led the hard conversations, shaped the architecture decisions that mattered, and built the things others benchmark against — and you are looking to do that across a growing portfolio of varied and interesting customers — this is the role for you.

What You'll Do

• Lead end-to-end ML assessments across infrastructure, data pipelines, model lifecycle, and organizational readiness — producing recommendations that drive executive decision-making and earn Caylent the next engagement.
• Partner with sales and solutions teams through the proposal and scoping phase, contributing the technical depth needed to shape well-grounded statements of work.
• Serve as the senior technical authority on client engagements — possibly across multiple projects simultaneously — providing architectural guidance, ensuring technical quality from your project team members, and getting hands-on when the engagement demands it, without owning day-to-day implementation responsibilities.
• Own or orchestrate high-quality POCs that give customers confidence before committing to a larger initiative.
• Advise customers on ML operations standards and architecture — covering MLOps pipeline design, model lifecycle management, LLMOps patterns, and production monitoring frameworks — translating operational complexity into decisions and guardrails their teams can own and sustain.
• Shape how Caylent wins its most technically complex opportunities — contributing the architectural thinking and credibility that turns prospects into customers.
• Strengthen the ML practice from the inside — through peer guidance, technical interviews, and contributions to accelerators, reference architectures, and thought leadership content.

What You Bring

The non-negotiables

• 10+ years in machine learning or AI, with a proven track record of leading client-facing engagements in a consulting or advisory capacity.
• Deep, current knowledge of the AWS ML and GenAI ecosystem, with the ability to make and defend architectural decisions across the full ML lifecycle — from data and feature engineering through training, deployment, and monitoring.
• Deep expertise in at least two or three ML domains — whether traditional ML, computer vision, NLP, time series, or others — combined with the judgment to assess, architect, and advise across the broader ML landscape.
• Proven ability to architect and govern production ML systems end-to-end, translating MLOps, LLMOps, and broader AI operations complexity into standards and decisions that engineering teams can execute and executives can act on.
• Deep expertise across foundation model adaptation — fine-tuning (LoRA, QLoRA, PEFT), alignment (RLHF, DPO), inference optimization (quantization, vLLM), and distributed training (DeepSpeed, FSDP) — combined with RAG and agentic system design, including multi-agent architectures, event-driven workflows, MCP integration, and human-in-the-loop patterns on AWS. Technical authority to prescribe the right approach and set architectural standards that teams can execute against.
• Proven ability to operate independently in complex customer environments — navigating ambiguity, aligning stakeholders, and translating ML tradeoffs into business risk and value for both technical and executive audiences.

Strong differentiators

• AWS Certified Machine Learning – Specialty and/or AWS Certified Solutions Architect – Professional.
• Experience shaping practice-level standards, reference architectures, and reusable ML accelerators across multiple engagements.
• Exposure to varied industries and problem types in a consulting or client-facing context.
• Deep fluency in responsible AI practices — model evaluation, bias detection, fairness frameworks, and AI governance — applied in enterprise deployments.
• Hands-on experience designing and deploying SRE agents and AI-driven operations workflows in production — spanning automated incident detection, triage, and remediation — with the ability to integrate across observability platforms and translate AI operations outcomes into measurable business value.

Technical Stack

Our practice spans a broad range of ML domains. Candidates are expected to prescribe — not just recognize — with the judgment to maximize what AWS makes possible and the experience to know how open-source tooling strengthens it.

ML Domains: Classical ML, Computer Vision, NLP, Generative AI & LLMs, AI Agents & Autonomous Systems, Intelligent Document Processing, Video Understanding, Speech & Audio, Time Series & Forecasting, Recommender Systems, Graph ML, Reinforcement Learning, Multimodal AI

AWS ML Platform: SageMaker, SageMaker Pipelines, SageMaker Feature Store, SageMaker Model Registry, SageMaker Clarify, Bedrock (Agents, Knowledge Bases, Guardrails, AgentCore, Model Evaluation)

Multi-provider LLM: Bedrock, Anthropic API, OpenAI API, Google Gemini API, Azure OpenAI — with the judgment to reason across provider tradeoffs in enterprise contexts

AWS AI Services: Rekognition, Comprehend, Transcribe, Textract, Translate, Personalize, Neptune, Kinesis Video Streams, Polly

Data Platform: Apache Spark / PySpark, Apache Kafka, Amazon Kinesis, Apache Iceberg, Delta Lake, Apache Hudi, AWS Glue

Vector Databases: Pinecone, pgvector, Amazon OpenSearch (vector), Weaviate

Frameworks: PyTorch, TensorFlow, JAX, Scikit-learn, XGBoost, HuggingFace (Transformers, PEFT, TRL), LangChain, LlamaIndex, DSPy, Ollama

MLOps & Governance: MLflow, W&B, Airflow / MWAA (data orchestration), Dagster (asset-based pipelines), Kubeflow Pipelines, CI/CD, IaC (CloudFormation, CDK, Terraform), Docker, Kubernetes, ML Governance (lineage, data contracts, audit), Responsible AI / Bias & Fairness

LLM Evaluation & Safety: RAGAS, LLM-as-judge patterns, DeepEval, NeMo Guardrails, Constitutional AI patterns, structured output validation

Inference & Optimization: Triton, vLLM, SGLang, Trainium, Inferentia, Quantization (GPTQ, AWQ, bitsandbytes), SageMaker Neo

WHY DEPT®?

We are pioneers at heart. What this means, is that we are always leaning forward, thinking of what we can create tomorrow that does not exist today. We were born digital and we are a new model of agency, with a deep skillset in tech and marketing. That’s why we hire curious, self-driven, talented people who never stop innovating.

Our culture is big enough to cope and small enough to care. Meaning, that with people across 20+ countries, we’re big enough to provide you with the best tools, global opportunities, and benefits that help you thrive. While acting small by investing in you, your growth, your team, and giving you the autonomy to solve our clients’ problems, no matter where you are in the world. 

We seek a Principal QA Automation Engineer with a strong background in Cypress, JavaScript/TypeScript, and proven experience working in AI-driven applications within an AWS cloud environment. This is a hands-on leadership role for someone who thrives at the intersection of quality engineering, automation strategy, and modern AI integration. As a senior technical leader, you will own the design, development, and maintenance of a robust test automation framework, ensure seamless integration with CI/CD pipelines, and bring forward-thinking approaches to testing intelligent, adaptive systems.

KEY RESPONSIBILITIES

• Lead the design and implementation of end-to-end test automation frameworks using Cypress with TypeScript.
• Define quality strategies for applications with AI/ML components, including deterministic and non-deterministic testing approaches.
• Collaborate with engineering, DevOps, and AI/ML teams to ensure quality across AI-infused features in production environments.
• Build and scale testing strategies for threaded AI applications running in AWS cloud infrastructure.
• Integrate automated tests into CI/CD pipelines to support frequent, reliable deployments.
• Mentor and guide mid- and senior-level QA engineers, setting best practices and driving a culture of quality-first development.
• Evaluate and introduce new tools, libraries, and frameworks to improve test coverage, performance, and developer experience.
• Participate in architectural discussions to ensure testability and reliability are baked into software designs from the start.
• Analyze test results, track quality metrics, and communicate risk and coverage to stakeholders.

QUALIFICATIONS

• 4+ years of hands-on experience with Cypress for UI and end-to-end automation testing.
• Expert-level proficiency in TypeScript, JavaScript and Python
• Proven experience testing AI-powered or machine learning applications, including AI model validation techniques.
• Strong understanding of AWS services (e.g., Lambda, S3, SQS, CloudWatch, ECS/EKS) and how to validate applications deployed in cloud environments.
• Experience with threaded/multi-agent AI tools and how they impact test design and validation.
• Familiarity with version control (Git), containerization (Docker), and CI/CD pipelines (e.g., GitHub Actions, Jenkins, or CircleCI).
• Strong communication, leadership, and mentoring skills.

PREFERRED QUALIFICATIONS

• Knowledge of AI model evaluation, model versioning, and monitoring tools (e.g., SageMaker, MLflow, LangChain, Vector Databases).
• Experience testing APIs, microservices, and event-driven architectures.
• Background in testing non-deterministic systems, including applying statistical or heuristic testing approaches.
• Contributions to open-source testing or AI tools are a plus.

WHAT DO WE OFFER?

• We enjoy spending time together, working closely with other local colleagues, and getting to know one another. Our Buenos Aires offices (Villa Crespo or Mar del Plata) are fully equipped with refreshments and great common spaces!
• Premium healthcare through OSDE for the employee and their immediate family members
• Mendel prepaid card with a monthly allowance for grocery purchases
• Monthly reimbursements for Wi-Fi/electricity expenses
• Monthly reimbursements for training/English classes
• 100% covered “Plan Total” membership at Sportclub
• Access to a our benefits platform through Bonda
• A flexible vacation policy

WE SUPPORT YOU BEING YOU

DEPT® is an equal opportunity employer (EOE). We believe our work is at its best when our people feel safe and free to be themselves. We’re committed to an inclusive and barrier-free recruitment and selection process and workplace, regardless of anyone’s lived experience, race, color, religion, sex, national origin, age, disability, and genetic information. So tell us about any accommodations you need. It’s totally confidential and only used to make sure you feel fully supported at every step.

We are a B Corp-certified company passionate about purpose-driven work. Our hope is that you can feel good about the contributions DEPT® is making to the world, and we always have an open door for your ideas in making the world a better place.

DEPT® is a pioneering technology and marketing services company that creates integrated end-to-end digital experiences for brands such as Google, KFC, Philips, Audi, Twitch, Patagonia, eBay and more. Its team of 2,500+ digital specialists across 30+ locations on 5 continents delivers pioneering work on a global scale with a boutique culture.

Learn more about DEPT®

DIVERSITY, EQUITY, & INCLUSION

At DEPT®, we take pride in creating an inclusive workplace where everyone has an equal opportunity to thrive. We actively seek to recruit, develop, nurture, and retain talented individuals from diverse backgrounds, with varying skills and perspectives.

Not sure you meet all qualifications? Apply, and let us decide! Research shows that women and members of underrepresented groups tend not to apply for jobs when they think they may not meet every requirement, when in fact they do. We believe in giving everyone a fair chance to shine.

We also encourage you to reach out to us and discuss any reasonable adjustments we can make to support you throughout the recruitment process and your time with us.

Want to know more about our dedication to diversity, equity, and inclusion? Check out our efforts here.