Shop Your Way - Head of Product

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

Requirements

• Highlight your experience building end‑to‑end fintech products (e.g., payments, loyalty platforms, or credit‑card integrations) by preparing a 2‑page product case study that details the problem, your roadmap, cross‑functional execution, key metrics (activation, NPS, revenue lift), and any regulatory hurdles you navigated—share this as a PDF link in your application and reference it during the interview.
• Demonstrate mastery of data‑driven decision making: include examples where you used tools such as Mixpanel, Amplitude, or Snowflake to surface insights that reshaped product strategy, and be ready to walk through a live “product analytics deep‑dive” exercise the interviewers may give you.
• Show you can lead remote, multidisciplinary teams at scale: cite specific remote collaboration frameworks you’ve instituted (e.g., quarterly OKRs synced in Asana, weekly async stand‑ups in Notion, and quarterly in‑person “innovation sprints”), and prepare a short slide deck showing how you kept alignment across engineering, design, compliance, and marketing while launching a fintech feature globally.
• Emphasize experience with compliance, security, and partnership ecosystems crucial to SYW’s “Pay Your Way” service: list any PCI‑DSS, GDPR, or SOC‑2 compliance projects you oversaw, and be prepared to discuss how you balanced speed of innovation with risk mitigation when integrating third‑party credit or loyalty partners.
• When discussing compensation, research recent Head of Product salaries for high‑growth fintech startups (typically $200‑$260 k base + 0.2‑0.4 % equity) and frame your ask around the value you’ll deliver—e.g., “I’m targeting a package that reflects my track record of delivering $50 M+ incremental revenue in the first 12 months of product launch, plus equity that aligns with long‑term growth of SYW.”