Shop Your Way - Head of Solutions Engineering (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: Head of Solutions Engineering, B2B The Head of Solutions Engineering - B2B is responsible for driving the overall technology solutions, architecture and deployment of cloud-based services supporting our B2B partnerships. In this position, you will provide technology leadership, guidance and architectural design decisions and will lead and support software engineers in deploying platform and product services.

Key Responsibilities

: Experience leading PreSales and/or developing PreSales technology strategies. Lead and assist in documentation, design, develop and deploy developers portal providing access tokens, APIs and SDKs for new and existing partnerships. Proven experience developing technical go-to-market deployment solutions and strategies in collaboration with business development, product management, product marketing and engineering teams. Ability to demo and evangelize developers platforms, APIs and SDKs. Ability to roll up sleeves and deploy prototypes to support B2B decision support. Is up to speed on modern web and mobile technologies we use Javascript/TypeScript, Java, C# .NET Core, React, Postgres, Swift, and AWS lambdas, RDS, fargate ECS, API Gateways, SNS/SQS/DLQ Serve as Scrum Master who have worked in a fast paced hybrid agile environment to ensure business and product objectives are achieved. Experience managing software development teams, and lead technical analysis & design, evaluate tradeoffs, and develop standards of excellence. Lead teams in exploring and solving hard problems with data driven iterative software development. Good understanding of architecture and design patterns for SaaS/Cloud and strong experience with at least one of AWS, Google or Azure. In-depth knowledge of Microservices based architectures. Building and maintaining strong relationships and earning and maintaining confidence with both customers and business leaders are critically important responsibilities for this role. Ability to identify and remove impediments, while successfully driving towards key initiatives.

Requirements

: Bachelor's Degree in Computer Science, Engineering with a minimum of 8+ years or proven hands-on experience deploying B2B and enterprise SaaS platforms and products. 5+ years of working leadership experience, operating in a player/coach role alongside other solutions engineers. 6+ years of software + hardware architecture experience . 6+ years productizing applications in an enterprise environment.

• Craft a data‑driven “Solutions Architecture” showcase: Build a 2‑page PDF case study that walks through a real or simulated B2B integration you designed (e.g., linking a retailer’s loyalty program to a credit card API). Include high‑level flow diagrams, key Excel‑based ROI models (cost‑benefit, adoption forecasts), and the exact metrics (e.g., 15% lift in repeat purchase) you projected. Attach this as an appendix to your resume and reference it in your cover letter.
• Quantify every engineering win with Excel metrics: The posting calls out Excel as a skill—turn that into a differentiator by preparing a short “Metrics Dashboard” (single Excel workbook) that summarizes past projects: number of APIs integrated, transaction volume handled, latency improvements, and revenue impact. Highlight formulas, pivot tables, and visualizations you built; be ready to walk interviewers through the workbook live.
• Demonstrate remote‑first collaboration fluency: Set up a brief demo (5‑minute video or live screen share) of how you run cross‑functional solution reviews using tools like Miro, Confluence, and Slack. Show a real meeting agenda, decision log, and how you capture action items in a shared Excel tracker. Send the link ahead of the interview or share it when asked about “remote teamwork.”

• Align your narrative with Shop Your Way’s “Pay Your Way” vision: Research SYW’s recent press releases on the SYW Mastercard and Rewards platform. In your interview, cite one specific product feature (e.g., real‑time loyalty point accrual at checkout) and propose a concrete engineering improvement—such as a micro‑service redesign that reduces point‑sync latency from 2 seconds to <500 ms, backed by an Excel simulation of cost vs. user‑retention gain.
• Prepare a salary‑negotiation script that references market‑adjusted remote comps: Use publicly available data (e.g., Levels.fyi, Glassdoor) for Head of Solutions Engineering roles in FinTech with 100% remote work. Build a simple Excel comparison table that maps base salary, equity, and benefits against cost‑of‑living adjustments for major US tech hubs. Present this table when the offer stage arrives to justify your target range confidently.