Pay Your Way - Credit as a Service: Head of Sales, Magento Platform

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 Sales - Magento The PYW Credit-as-a-Service team is looking for an individual who can be a foundational asset to the Sales team. This role is the Head of Sales responsible for our expanding merchant/retailer partnerships within the Magento ecosystem. 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. Primary

Responsibilities

• Build a one‑page “sales funnel dashboard” in Google Sheets that maps the entire Magento ecosystem (partners, merchants, integration points) and includes metrics you’d track (pipeline value, conversion rates, average deal size). Bring this sheet to the interview and walk the interviewers through how you’d use it to forecast revenue and identify bottlenecks—showcasing both your Excel/Sheets mastery and strategic thinking for a SaaS/FinTech sales org.
• Prepare a short case study (2–3 pages) of a previous “never‑been‑done‑before” go‑to‑market launch you led, focusing on how you aligned product, engineering, and sales teams to create a new credit or loyalty offering. Highlight measurable results (e.g., % YoY revenue lift, merchant adoption speed) and tie the narrative to Shop Your Way’s Pay Your Way value proposition.
• Research the top 5 e‑commerce brands that currently run on Magento and are publicly known to use loyalty or credit programs. Draft a personalized outreach email (including a one‑pager) that outlines a concrete growth hypothesis for each brand using SYW’s combined loyalty + credit stack. Bring this as a portfolio piece to demonstrate market insight and immediate pipeline ideas.
• During the interview, ask data‑driven questions about SYW’s current sales velocity on the Magento platform (e.g., average sales cycle length, churn rate of merchant accounts, ARR per integration). Then propose a quick‑win experiment—such as a “co‑sell pilot” with a Magento development agency—showing you can translate analytics into actionable revenue experiments.
• When negotiating compensation, benchmark the Head of Sales salary for remote fintech roles (typically $180‑$250k base + 0.5‑1.5% equity) and prepare a value‑add worksheet that quantifies the incremental revenue you expect to generate in the first 12 months (e.g., $5M‑$8M). Use this worksheet to justify a higher base or a performance‑based accelerator tied to Magento‑specific milestones.