---
title: 'Shop Your Way - Head of Legal Solutions (Credit & Loyalty) at Shop Your Way'
canonical: 'https://feeny.ai/job/shop-your-way-head-of-legal-solutions-credit-loyalty-shop-your-way-united-states-4fghdv329hz7'
type: 'job'
last_seen: '2026-09-07'
---

# Shop Your Way - Head of Legal Solutions (Credit & Loyalty) 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/ce8fe894-aea0-4424-93ab-8fe682b04f07

## 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 Legal Solutions (Loyalty + Credit)

The Head of Legal Solutions (Loyalty + Credit) is responsible for leading, driving, and implementing all legal, risk, compliance and related initiatives for the SYW Rewards and Mastercard programs. Notably, this role will serve as the Legal Lead with our partners at Citibank and elsewhere.  This leader will build the foundation for compliance based marketing in the fintech space.

## GROW THE BUSINESS (80% FOCUS)

- Lead initiatives and manage high-impact special project work streams with a results-driven focus to deliver solutions across: credit and lending, consumer protection & privacy, and financial services marketing
- Translate new business development strategy, goals, and initiative details in a succinct and clear manner; provide direction and guidance on the programs for/with/to Citibank
- Accelerate speed to market of new opportunities by being the single point for legal review of contracts, as well as with Citibank
- Develop the legal operating model and processes that move with speed while maintaining the required level of risk and compliance rigor
- Engage with the product and function coverage teams, in order to partner to develop and apply Program solutions that meet the function/business/product and customer needs in a manner consistent with the Citi program framework
- Develop creative solutions and well-reasoned legal-business cases that accelerate and advance the go-to-market efforts
- Advise function/business/product management and teams on regulatory and compliance issues; develop and “sell in” credible challenges and arguments in favor of the solutions
- Serve as a subject matter expert on Citi’s Compliance programs. Provides expert guidance on function/business/product regulations on a real-time basis to manage compliance risk

## RUN THE BUSINESS (20% FOCUS)

- Oversee the monitoring and identification of regulatory developments, including enforcement actions, and new laws, regulations, rules, and interpretations or guidance relating to the supported function/business/product
- Anticipate and address potential legal risks with business partners
- Analyze and scope the impact of new and complex regulatory developments across senior function/business/product, including cross partner implications
- Manage strategy and responses to regulatory examinations, reviews and inquiries and internal and external investigations, as well as testing and audit
- Serve as the senior compliance risk officer responsible for establishing internal strategies, policies, procedures, processes, and programs to prevent violations of law, rule, or regulation and design and deliver a risk management framework that maintains risk levels
- Understanding the evolution of the Consumer Financial Protection Bureau (CFPB) to guide our business as we continue to evolve both our technology and marketing platformsDesign and lead compliance and control reviews

Requirements:

- J.D. Degree with a minimum of 8+ years or proven hands-on experience driving and supporting credit product, credit marketing, and credit risk/compliance programs across branded, co-branded, and/or general-purpose cards
- Deep understanding and experience in consumer lending and protection, including Compliance laws, rules, regulations, risks and typologies; including but not limited to CCPA, TCPA, GDPR, and more3+ years experience with credit card marketing
- Fair Lending & Consumer Financial Protection Act expert
- Experience with advising teams leveraging algorithms and business specific data to serve credit card ads to potential customers
- Strong presentation skills with the ability to articulate complex problems and solutions through concise and clear messaging
- Excellent written, verbal and analytical skills
- Must be a self-starter, flexible, innovative and adaptive; able to successfully navigate complex and novel legal/business situations
- Highly motivated, strong attention to detail, team oriented, organized

## 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