Flex

• Design, build, and own the data pipelines and ML services that classify product eligibility and power downstream decisions across Flex • Model the data domain (products, merchants, eligibility rules, classifications, and outcomes) in warehouses and serving systems other teams build on • Partner with backend, product, and operations stakeholders translating merchant and consumer needs into reliable data products, models, and APIs • Own and improve the architecture of the data warehouse, transformation layer, ML training and inference systems, and real-time serving paths • Analyze, troubleshoot, and resolve production issues rooted in data quality, model accuracy, pipeline reliability, and serving latency • Collaborate on cross-functional projects connecting the full Flex experience, from consumer checkout to merchant analytics • Build and maintain evaluation harnesses, golden datasets, and observability for the models and pipelines you ship • Create and maintain documentation for data models, pipelines, and on-call runbooks • Contribute to a culture of learning, problem-solving, and operational excellence

• Run the marketing launch of new partners and drive ongoing adoption through campaigns and always-on programs • Support the Partner Marketing Lead on annual co-marketing planning with top partners, balancing tentpole campaigns with always-on programs • Drive day-to-day execution of 360 marketing campaigns across social, email, marketplace, and beyond, including cross-merchant campaign activity • Act as the main day-to-day marketing contact for marketing leads, building and nurturing those external relationships • Collaborate with Partner Success, Sales, and Marketing to align on goals and grow our partnerships • Work closely with the Partner Success team and keep them informed on marketing best practices, sharing playbooks and learnings from across our portfolio • Build and maintain the internal processes and external documentation that keep a high volume of partner campaigns launching on time • Apply a test-and-learn mentality across creative concepts, paid and organic channels, and partner playbooks, iterating quickly on what works

• Own the operational backbone of this venture from day one - concept through execution • Drive regulatory readiness and stay ahead of the compliance requirements that come with operating in a regulated healthcare environment • Design and improve the workflows that keep the operation running - and running well. • Stand up the full network: recruiting, onboarding, and performance management • Define the metrics that matter - turnaround time, quality, throughput, compliance - and build the dashboards and rituals around them • Partner with Flex's product and engineering teams to translate operational needs into platform requirements • Write the playbooks, policies, and documentation that let this operation scale beyond you

• Design, build, and own backend services and APIs that power Flex’s applications • Model the domain - eligibility rules, transactions, merchants, consumer accounts, etc. - in data structures and APIs that other teams build on • Partner with frontend, design, and business stakeholders to translate merchant and consumer needs into reliable APIs and workflows • Own and improve our backend service architecture, data models, and integrations • Analyze, troubleshoot, and resolve production issues rooted in business logic, data correctness, and transactional edge cases • Collaborate on cross-functional projects that connect the full Flex experience, from consumer checkout to merchant analytics • Create and maintain documentation for APIs, services, and on-call runbooks • Contribute to a culture of learning, problem-solving, and operational excellence

• Design, build, and operate the cloud infrastructure, databases, and core systems that engineering teams build on • Partner with backend, frontend, and other stakeholders to translate their needs into reliable platform capabilities • Own and improve our cloud infrastructure, databases, and observability stack • Analyze, troubleshoot, and resolve production issues rooted in infrastructure, scaling, and reliability • Collaborate on cross-functional projects that connect the full Flex experience, from consumer checkout to merchant analytics • Create and maintain documentation for infrastructure, platform services, and on-call runbooks • Contribute to a culture of learning, problem-solving, and operational excellence

• Lead frontend development using React across multiple applications • Ship high-quality experiences with a bias towards execution • Partner with business stakeholders to ensure needs are addressed • Own and improve frontend architecture while identifying and closing experience gaps • Collaborate on cross-functional projects connecting the full Flex experience • Contribute to a culture of learning, problem-solving, and operational excellence

• Own product design end-to-end on the merchant team, from discovery and user research through final UI and shipping with engineers • Lead user research: run merchant interviews and surveys, hop on sales and customer calls, and turn what you learn into clear product direction • Partner with engineering and the founding team to define the merchant roadmap, scope features, and ship quickly without sacrificing craft • Design clear, well-considered user flows in Figma and the visual UI to support them • Use AI tools (Claude, Cursor, Cowork, v0, etc.) to prototype, validate, and iterate on ideas faster than traditional design workflows allow • Collaborate with our team on evolving and maintaining the Flex design system • Pitch in across the company when needed (the occasional marketing asset, website tweak, or one-off) without needing it to be your job description • Contribute to a culture of learning, problem-solving, and operational excellence

• The technical narrative for every enterprise deal, from first discovery call through security review, integration design, and go-live • Custom integration architectures for complex merchant-built checkouts. The bulk of this work is direct API integration with sophisticated, custom commerce stacks • Live POCs, sandbox demos, and integration walkthroughs that move six- and seven-figure deals across the line • The structured feedback loop into product and engineering, synthesizing what enterprise prospects need, where we're losing on capability, and where the next durable bet is • Reusable enablement assets, including reference architectures, integration playbooks, security and compliance one-pagers, and ROI models that scale the GTM team • Smooth handoff to customer success and engineering for post-sale implementation

• Contribute to building the highest-converting HSA/FSA checkout experience. • Build simple, elegant APIs that make Flex easy to integrate. • Design and develop scalable solutions for HSA/FSA payment infrastructure. • Interact directly with customers to help define the roadmap. • Work with technologies including Next.js, Rust, TypeScript, Postgres, Redis, and AWS.

• Triage and respond to daily merchant and customer tickets via Slack and Pylon • Ensure we meet SLA targets and maintain a high bar for customer satisfaction • Deliver clear, thoughtful, and technically sound responses across internal and external communications • Work closely with Engineering, Product, and Operations teams to unblock support issues • Contribute to internal tooling using Retool, Metabase, and SQL to help automate workflows • Collaborate on internal projects to help the Support team scale efficiently • Ensure broader internal team has tools and visibility needed for great customer experience • Partner with Engineering to test new product functionality and backend fixes