Shop Your Way - Program Manager, B2B

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: Program Manager, B2B The B2B-PBO Program Management role in the PYW Team requires strong project management, analytical, and process optimization skills. You will deliver programs across teams and/or multiple channels. The ideal candidate must be comfortable working independently in a fast-paced environment, demonstrate solid business judgment, and possess the ability to influence both internal and external partners.

Key Responsibilities

Preferred Qualifications

• Show deep fintech & loyalty‑program knowledge: In your résumé and cover letter, cite concrete projects where you built or scaled payment, rewards, or credit‑card integrations (e.g., launched a token‑based loyalty engine, migrated a legacy payments stack to a cloud‑native API). Mention the specific platforms (Stripe, Visa Direct, AWS Lambda, Kubernetes) you used, and quantify impact (e.g., “increased transaction volume × 1.8, reduced settlement latency by 30%”). Recruiters at Shop Your Way flag candidates who already speak the language of their core services.
• Create a one‑page “Program Dashboard” portfolio: Build a PDF or web page that mirrors a product‑owner dashboard—include a timeline, KPI targets, risk‑mitigation matrix, and stakeholder map for two of your most relevant programs. Highlight how you coordinated cross‑functional teams (tech, compliance, marketing) in a remote setting, and embed screenshots of JIRA/Asana boards or Tableau dashboards (blur sensitive data). Send the link in your application and reference it during the interview.
• Demonstrate remote‑first program management chops: Prepare concrete examples of running fully distributed sprints across time zones—show how you set “core‑hours” syncs, used async status updates in Confluence, and leveraged tools like Miro for visual collaboration. Mention any certifications (e.g., Scrum Master, PMP) and the exact metrics you improved (e.g., “burn‑down variance reduced from 15% to 4% after instituting daily async stand‑ups”).
• Anticipate the “innovation & scale” interview theme: Be ready to walk through a case study where you took a “never‑done‑before” feature from concept to production at scale (e.g., a real‑time loyalty‑points redemption engine handling >10 M daily users). Prepare a 5‑minute slide deck that outlines problem, hypothesis, MVP design, tech stack, scaling strategy, and post‑launch results. Practice articulating trade‑offs between speed, compliance, and user experience—key criteria for SYW’s B2B product line.
• Negotiate with data on remote compensation benchmarks: Research recent Salary.com and Levels.fyi data for “Program Manager, B2B FinTech” remote roles (average base $130‑$155 k, total % target ≈ 20‑30 % bonus + equity). In your offer discussion, cite your proven ROI (e.g., “delivered $3 M incremental revenue in 12 months”) and request a compensation package that matches or exceeds the 75th percentile of the market. Emphasize the value of remote flexibility and ask for a clear equity vesting schedule aligned with SYW’s growth milestones.