---
title: 'Pay Your Way - Credit as a Service: Head of Sales, Magento Platform at Shop Your Way'
canonical: 'https://feeny.ai/job/pay-your-way-credit-as-a-service-head-of-sales-magento-platform-shop-your-way-f961m01qz8ek'
type: 'job'
last_seen: '2026-09-07'
---

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

- **Company:** Shop Your Way
- **Location:** United States
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2022-10-13
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.lever.co/syw.com/e04817ad-35e3-45b3-887d-447ef1ef15e0

## Job description

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:

- Identify and manage new market opportunities via partnerships with Magento platform merchants
- Identify and manage new market opportunities via partnerships.
- Identify new partners
- Manage existing partners and expand reach of products within the existing partner network.
- Understand our product offerings and be able to clearly explain the key features, pros/cons of various solutions to our partners. Analyze market data and perform competitive product analysis
- Identify opportunities and strategies to help partners achieve their specific goals by aligning PYW’s solutions with partner’s business objectives.
- Communicate with internal teams at all levels and functions across the [organization.In](http://organization.In) partnership with the CRO, formulate and document strategy and objectives for cross-functional teams, along with day-to-day tools such as timelines and stakeholder action items, required to achieve success.
- Collaborate with internal stakeholders, partners, vendors, and customers to achieve strategic objectives.

Education and/or Experience:

- Bachelor’s degree required
- 5+ years of relevant work experience or equivalent experiences in  Sales, Business Development, and/or Partnerships.
- Advanced level experience working with Excel, PowerPoint, Word and/or Google Docs, Google Sheets.
- Experience in Fintech, commerce, software-as-a-service, or consumer internet industries preferred.

## About Shop Your Way

## Company Overview
- **One-liner**: Shop Your Way (SYW) is a high-growth FinTech and partner-enablement platform that powers loyalty, payments, and data services for some of the largest brands in America.
- **Entity Type**: Private (Privately Held, Transform SR Brands, LLC)
- **Headquarters**: Hoffman Estates, Illinois, USA
- **Founded**: 2009
- **Founders**: Not publicly available

## Core Business
- **Primary industries**: FinTech, Loyalty Programs, Payments, Data Services, Consumer Services
- **Target customers**: B2B (brands, retailers, financial institutions) and B2C (consumers through rewards programs); mid-market to enterprise clients
- **Mission / purpose**: “Built for scale & growth” – enabling partners to enhance customer engagement through integrated loyalty, payments, and data solutions.

## Products & Services
- **SYW Rewards Platform**: A proprietary loyalty and rewards engine that allows brands to manage points, offers, and member engagement.
- **SYW Mastercard / Shop Your Way 5321 Visa Credit Card**: Co-branded credit cards that integrate rewards with everyday spending (launched in 2025 in partnership with Fidem Financial and Transformco).
- **Sears Home Advantage**: A free membership program for homeowners, powered by Shop Your Way (launched 2024).
- **Digital Properties & Partner Network**: A scalable technology infrastructure that powers multiple consumer-facing digital properties and a growing network of partner brands.

## Market Standing
- **Valuation / Market Cap**: Not disclosed
- **Key Metric**: Estimated annual revenue between $250M and $500M (LeadIQ, 2026) – *not publicly confirmed*
- **Notable Investors / Partners**: Transformco (parent), Fidem Financial, Unifimoney (SYW invested in Unifimoney), Way.com (partnership)
- **Growth Signals**: 
  - Launch of new co-branded Visa credit card (Nov 2025)
  - Expansion into home services with Sears Home Advantage
  - Headcount data conflicts: one source reports 24 employees (with -1.9% YoY), another reports ~103 employees (LeadIQ) – likely the larger figure reflects the full SYW entity including Transformco support. Recent job postings indicate active hiring for remote roles.

## Competitive Advantages
- **Proprietary technology stack**: Microservices-based, cloud-native infrastructure that enables rapid integration and scaling for large enterprise partners.
- **Expansive partner network**: Relationships with major brands and retailers (e.g., Sears, Kmart) and emerging fintech partners.
- **Integrated model**: Combines loyalty, payments, and data services in a single platform, reducing complexity for clients.
- **Patent portfolio**: Multiple granted patents in social shopping, personalization, and gesture-based commerce (2019–2024).

## Strategic Focus
- **Scaling the partner network** and onboarding new brands across retail, financial services, and home services.
- **Expanding financial services** through co-branded credit cards and embedded lending (e.g., “Credit as a Service” mentioned in job postings).
- **Enhancing data and personalization capabilities** to drive member engagement and retention.

## Why Work Here
- **Culture**: High-growth FinTech environment with a focus on innovation and scale; described as “built for scale & growth.”
- **Work policy**: Remote-friendly with a remote work program; job postings are listed as “Remote – Full-Time U.S.A.” (Lever). However, the company also has an onsite office in Hoffman Estates, IL.
- **Perks**: Health insurance, dental insurance, and a remote work program (Built In).
- **Engineering culture**: Technical team includes Senior Director of Engineering, Technical Lead; tech stack includes microservices, fintech, Segment, and Martech.
- **Growth opportunity**: As a private company with a strong partnership network, employees can work on high-impact projects for Fortune 500-level brands.

## Sources
1. [Built In – Shop Your Way Company Profile](https://builtin.com/company/shop-your-way-syw)
2. [LinkedIn – Shop Your Way Company Page](https://linkedin.com/company/shop-yourway)
3. [LeadIQ – Shop Your Way Company Overview](https://leadiq.com/c/shop-your-way/5ac549195400005201ba69c5)
4. [Lever – Shop Your Way Careers Page](https://jobs.lever.co/syw.com/)
5. [Shop Your Way Website](https://www.shopyourway.com/)
6. [PR Newswire – Unifimoney Seed+ Investment from Shop Your Way](https://www.prnewswire.com/news-releases/unifimoney-secures-seed-investment-from-shop-your-way-301487932.html)
7. [Newswire – Way.com Partnership](https://www.newswire.com/news/way-com-unlocks-new-ways-for-users-to-save-with-shop-your-way-partnership)

## Other roles at Shop Your Way

- [Shop Your Way - QA Engineer](https://feeny.ai/job/shop-your-way-qa-engineer-shop-your-way-hyderabad-h2n0k47bn8hr) — Hyderabad, India
- [Shop Your Way - React Native Developer](https://feeny.ai/job/shop-your-way-react-native-developer-shop-your-way-united-states-dc14cz4f8cct) — United States
- [Shop Your Way - DevOps Engineer](https://feeny.ai/job/shop-your-way-devops-engineer-shop-your-way-united-states-c7p38nq9qfgp) — United States
- [Shop Your Way - Full-Stack Software Engineer](https://feeny.ai/job/shop-your-way-full-stack-software-engineer-shop-your-way-united-states-sjqmdev7h4s4) — United States
- [Shop Your Way - Android Developer](https://feeny.ai/job/shop-your-way-android-developer-shop-your-way-united-states-k03n1xs5rmbw) — United States
- [Shop Your Way - Cloud Data/Systems Engineer](https://feeny.ai/job/shop-your-way-cloud-data-systems-engineer-shop-your-way-united-states-a00a73aybrjz) — United States
- [Shop Your Way - Product Manager, Payments](https://feeny.ai/job/shop-your-way-product-manager-payments-shop-your-way-united-states-a94pa2swctnt) — United States
- [Pay Your Way -Credit as a Service: Analyst, Sales Operations](https://feeny.ai/job/pay-your-way-credit-as-a-service-analyst-sales-operations-shop-your-way-united-7wzq6bz1a0sv) — United States
- [Pay Your Way -Credit as a Service: Sales Enablement Lead](https://feeny.ai/job/pay-your-way-credit-as-a-service-sales-enablement-lead-shop-your-way-united-dhmz4te1bppr) — United States
- [Shop Your Way - Product Marketing Manager](https://feeny.ai/job/shop-your-way-product-marketing-manager-shop-your-way-united-states-e56jrc72vtnp) — United States