Shop Your Way - DevOps Engineer

Do you consider yourself an innovator, a builder, a game-changer? Do you have what it takes to transform the payments, loyalty, and commerce space? Do you want to help develop and scale truly “never been done before” services and technologies? If yes, then we want to hear from you at Shop Your Way SYW Overview Shop Your Way (“SYW”) is a high-growth FinTech and e-Commerce enablement platform that leverages a proprietary technology infrastructure to service some of the largest and most innovative brands in America. SYW powers multiple business and consumer services, including SYW Rewards and the SYW Mastercard, along with a leading mobile app and digital destination. When bundled together as part of our Pay Your Way (“PYW”) service, we have a truly differentiated loyalty + credit solution for our business partners and their customers, without the hassle of setting up a direct credit relationship with a bank or underwriter. This integrated module makes it easy for Partners of any size to improve their conversions, drive new revenue, save on transaction and payment costs, and create more repeat business. Today, we’re providing this “loyalty-card as a service” to Raise (gift cards) and Way (mobility) – two of the “Andreessen Horowitz Top 50 Marketplaces” – and other national brands. Now, we’re expanding our offering to include other new application services while also unlocking new channels. SYW is at an exciting inflection point, built for scale and driving growth. Key Highlights include: ● Recent investment of +$30M of “growth capital” from Private Equity / Hedge Fund sponsor ● Long-term strategic partnership with Citibank powering a multi-billion dollar credit portfolio ● Compelling pipeline of New Business Development initiatives, focused on SYW 5321 Card Externalization (“loyalty-card as a service”) ● Proprietary, best-in-class loyalty and data technology platform built to power $10+ billion of partner business ● A sizable (9 million active) yet hyper local member base of active shoppers ● A valuable rewards currency, with more new places to burn – from gift cards to sports media to parking, car wash, electrical vehicle charging to crypto and ETFs ● A multi-tender, proprietary “wallet” with rewards, gift cards, and credit ● Platform can be white-labeled and quickly integrated into existing retail and loyalty systems https://business.syw.com/ Roles Summary: DevOps Engineer Will be responsible for automation and implementation of tools and processes which enable rapid development and deployment of software. Will guide the mission to cover continuous integration/deployment in a delivery pipeline that will perform automated system tests, deploy infrastructure and applications code quickly (including cloud and serverless), and provide operational metrics back to development and business teams. Will be solving incredible puzzles and troubleshooting unbelievable issues while maintaining the ShopYourWay Platform and Applications. Ideal candidates for this role will have a blend of development and operational experience that provides them with a good understanding of the developer team needs, while also balancing business satisfaction and maintaining production systems and applications uptime.

Requirements

• Highlight hands‑on experience with cloud‑native CI/CD pipelines (e.g., Jenkins, GitHub Actions, or AWS CodePipeline) by linking to a public repo or a short video walkthrough that shows you building, testing, and deploying a microservice to AWS (ECS/EKS) or Azure AKS—Shop Your Way emphasizes scaling “never‑been‑done‑before” services, so they’ll look for proven automation at scale.
• Showcase any prior work with payments‑oriented infrastructure (PCI‑DSS compliance, tokenization, or secure API gateways). Include a brief case study in your resume or a separate PDF that outlines the security controls you implemented, the compliance audits you passed, and the performance metrics you achieved.
• Demonstrate familiarity with the company’s tech stack by contributing a small open‑source plugin or Terraform module that provisions a “loyalty‑engine” style service (e.g., a points‑accrual microservice). Mention this contribution in your cover letter and be ready to discuss design decisions during the interview.
• Prepare to talk through a recent incident you owned end‑to‑end: detection, root‑cause analysis, remediation, and post‑mortem documentation. Shop Your Way values reliability in fintech; quantifying impact (e.g., “reduced latency by 30 %” or “prevented $150k in potential fraud”) will make you stand out.
• When discussing compensation, research recent remote DevOps salaries at high‑growth fintech firms (Glassdoor, Levels.fyi) and frame your ask around total‑compensation packages that include performance bonuses tied to service uptime or cost‑savings from infrastructure optimization—Shop Your Way often ties bonuses to measurable reliability improvements.