Shop Your Way - Head of Client Delivery

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/ Pay Your Way: Payments as a Service Pay Your Way (“PYW”) – a business unit, B2B(2C) product and platform inside SYW – is a new Credit-as-a-Service offering for Merchants, Digital Marketplaces, and more that want an embedded credit offering without the hassle of setting up a direct credit relationship with a bank or underwriter. We make 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. Our existing partnerships with clients such as Citibank, Raise.com, and others make the next generation of loyalty and credit a reality. Built on the latest technology, our roadmap has laid the foundation to enable innovation and growth for years to come. Role Summary: Head of Client Delivery The PYW Credit-as-a-Service team is looking for an individual who can be a foundational asset to the Partner Management team, including the Client Delivery Team. Specifically, we are looking for a Head of Client Delivery responsible for pre and post sales Client support and readiness. This role is an integral part of the pre-sales and post-sales discovery and implementation. While this role reports to the Product organization, cross collaboration with the Sales Team is a key component of this role. This role will serve as the technical voice of reason to our partners during the pre-sales and post-sales process. This is an opportunity to make a meaningful impact and create value for our customers through flexible tools that allow partners to leverage Pay Your Way capabilities within any Partner’s customer experience. In this role, you will join a team committed to being delivery-focused and creating the best possible customer experience, working towards an ambitious roadmap to differentiate Credit-as-a-Service for merchants. When joining our fast-growing team, you will be shaping high-profile and exciting new fintech products. Born out of the Digital Innovation space, our goal is to turn our vision into a market leading platform.

Key Responsibilities

Basic Qualifications

• Highlight concrete fintech delivery wins: in your résumé or interview, quantify end‑to‑end projects you led that launched payment or loyalty services (e.g., “Reduced onboarding time for 15 enterprise merchants from 12 weeks to 5 weeks, generating $3M incremental revenue in 6 months”). Use these numbers to demonstrate you can scale “never‑been‑done‑before” solutions.
• Showcase mastery of the tech stack that powers SYW’s platform: prepare a short case study (1–2 slides) showing your experience with cloud infrastructure (AWS/GCP), API‑first architecture, micro‑services, and CI/CD pipelines (Jenkins, GitHub Actions, Terraform). Emphasize any work integrating card‑issuing APIs or rewards engines, and be ready to discuss how you ensured security and compliance.
• Prove remote leadership fluency: list the collaboration tools you use daily (e.g., Slack, Zoom, Miro, Asana/Jira) and share a documented remote workflow that includes daily stand‑ups, KPI dashboards, and async decision‑making. Cite examples where you managed cross‑functional teams (product, engineering, compliance) across time zones and kept delivery on‑track.
• Prepare a “Client Delivery Playbook” as a portfolio piece: a 2‑page PDF outlining your methodology for client onboarding, SLA definition, risk mitigation, and scaling delivery operations. Include screenshots of dashboards, stakeholder maps, and a brief testimonial or metric from a previous employer to give interviewers a tangible artifact of your process.
• Arm yourself for salary negotiation with data: research US remote Head of Delivery compensation in fintech (e.g., base $180‑220k, target cash‑plus‑equity $250‑300k). Align your ask with measurable impact you can deliver (e.g., “My last role drove a 20% YoY increase in merchant activation, translating to $5M net new revenue”), and be prepared to discuss equity vesting cadence and performance‑based bonuses specific to SYW’s growth stage.