---
title: 'Shop Your Way - Head of Product at Shop Your Way'
canonical: 'https://feeny.ai/job/shop-your-way-head-of-product-shop-your-way-united-states-yrc062abw8v3'
type: 'job'
last_seen: '2026-09-07'
---

# Shop Your Way - Head of Product 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/3bb86e2d-693a-4063-a46d-0ea4f9bd1dca

## 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/

Role Summary: Head of Product

As a Head of Product Management, this role is responsible for delivering new payments and loyalty products as part of an overall portfolio serving both Members (B2C) and Partners (B2B, B2B2C).In this role, you will join, lead, and build a team committed to being delivery-focused and creating the best possible customer experience, working towards an ambitious roadmap to differentiate payments and loyalty. This is an opportunity to make a meaningful impact and create value for our business through delightful UX, revenue generating features, and a clear product ecosystem.

Responsibilities:

- Own and drive a product roadmap that meets business goals, achieves key performance indicators, and provide a world-class customer experience
- Deliver a new category of payment and loyalty programs and simplify the end-to-end experience
- Partner with customers, partners, and internal teams to understand product needs
- Collaborate with the executive team, Design, Engineering, Marketing, Sales, and Customer Success to build an end-to-end experience
- Lead feature definition and prioritization, internally informed by data analytics, product metrics, user experience research, competitive and market analysis, internal stakeholders and business goals
- Collaborate with stakeholders and partner with engineers and designers to deliver high-quality experiences
- Provide clear vision and documentation, including use cases and product requirements to support UX design, development, and operations support
- Build and present executive product updates, including performance metrics, delivery status, and roadmap updates
- Build a world-class Product Management team and mentor leaders and product managers on the team

Requirements:

- 15+ years experience building and launching FinTech products in the financial services industry10+ years experience and building high-performing and agile product teams
- Familiarity with payments and loyalty products, ideally in the B2B space and BaaS
- Track record of leading cross-functional teams in an Agile development environment
- Experience in process improvement and change managementProven analytical skills, problem-solving ability, and meticulous attention to detail
- Self-motivated, proactive team player who takes ownership of and accountability for projects
- Able to effectively manage competing priorities, manage tight delivery timelines, and stay calm under pressure
- Strong relationship-building and communication skills. Able to communicate complex issues to a wide array of internal stakeholders
- Working understanding of financial services regulatory environmentBachelor's degree required, MBA 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
- [Pay Your Way - Credit as a Service: Head of Sales, Magento Platform](https://feeny.ai/job/pay-your-way-credit-as-a-service-head-of-sales-magento-platform-shop-your-way-f961m01qz8ek) — United States