Vice President of Engineering

Company DescriptionFreely Payments is a venture-backed fintech company transforming payment acceptance for the $1 trillion-plus food distribution industry.Most wholesale distributors have historically avoided or limited card acceptance because of high processing costs. Freely changes that. Through exclusive network rates, intelligent transaction routing, interchange optimization, and innovative cash-back programs, Freely helps distributors reduce payment processing costs by as much as 50%—and, in certain programs, to near zero.Our platform enables distributors to improve cash flow, reduce credit risk, streamline accounts receivable, and offer customers greater payment flexibility and rewards. We are building an integrated B2B payments ecosystem that includes payment acceptance, automated reconciliation and cash application, merchant analytics, and co-branded card programs.Freely has already signed several of the largest distributors in the industry, with a growing backlog of contracted customers ready to be integrated and launched.Mastercard is both an investor and strategic partner in Freely, giving us access to differentiated network relationships and helping us build a new category of B2B payments. Our team is composed of experienced leaders in payments, food distribution, financial technology, and enterprise software who share a commitment to modernizing how distributors accept and manage payments.Role DescriptionThe Vice President of Engineering is a full-time, on-site leadership position based in Arlington, Virginia. This is a founding-level engineering role with responsibility for building and leading Freely’s engineering organization while shaping the architecture and technical direction of our payments platform.This is not a maintenance role. You will join a company with demonstrated product-market fit, meaningful payment volume, and signed customer demand. Your immediate priority will be translating that demand into live production volume by accelerating customer integrations and strengthening the systems that support onboarding, payment processing, billing, reconciliation, analytics, and reporting.As the platform grows, you will lead the development of automated reconciliation and cash-application capabilities that allow Freely to scale to billions of dollars in payment volume without increasing operational headcount at the same rate.You will work directly with the CEO, founders, product leaders, customers, processors, and strategic partners to translate business requirements into reliable and scalable technical solutions. You will also build and mentor the engineering team, establish development standards, and create a culture of accountability, urgency, collaboration, and technical excellence.Key ResponsibilitiesSet the technical vision, architecture, and engineering roadmap for Freely’s payments platform.Build, lead, and mentor a high-performing engineering organization.Remain sufficiently hands-on to evaluate architecture, review critical technical decisions, and help solve complex engineering problems.Lead development across distributor onboarding, payment processing, billing, reconciliation, cash application, reporting, and analytics.Accelerate integrations that move signed distributors from implementation into live production.Partner closely with product and business leadership to prioritize initiatives based on customer impact, revenue, risk, and strategic value.Establish engineering processes, development standards, documentation practices, and quality controls.Improve platform reliability, scalability, performance, security, observability, and operational resilience.Own technical resource planning, hiring, vendor evaluation, and engineering capacity.Establish meaningful engineering performance metrics and continuously improve delivery velocity and predictability.Communicate technical strategy, risks, tradeoffs, and progress clearly to executive and nontechnical stakeholders.Initial PrioritiesDuring the first six months, you will be expected to lead the delivery of several important initiatives, including:Integrations that move our backlog of signed distributors into live production.Automated reconciliation and cash application built directly into the Freely platform.A robust interchange-optimization and billing engine.Real-time merchant dashboards, reporting, and analytics.Production-grade monitoring, alerting, logging, and observability.Security enhancements across authentication, authorization, data access, infrastructure, and secrets management.A scalable engineering organization and operating model capable of supporting rapid growth.Technology EnvironmentOur current technology environment includes:Frontend: Angular, TypeScript, RxJS, and Tailwind CSSBackend: Node.js, TypeScript, and REST APIsInfrastructure: Google Cloud Platform, Cloud Run, GKE, Pub/Sub, Cloud SQL, and FirestoreEngineering tools: GitHub Actions, Sentry, Linear, and NotionExperience with every component of our current stack is not required, but candidates should have the technical depth to quickly understand the environment and make informed architectural decisions.Qualifications10 or more years of professional software engineering experience building and operating production software.Five or more years of experience managing and developing engineering teams.Demonstrated success building, leading, and scaling high-performing technical organizations.Strong hands-on software development background, with the ability to provide credible architectural and technical leadership.Advanced experience with Node.js, TypeScript, or comparable modern backend technologies.Experience designing and operating cloud-native, distributed, and event-driven systems.Proven ability to build secure, scalable, and highly available platforms that process sensitive or high-volume data.Strong understanding of API design, data architecture, system integrations, testing, deployment automation, and production operations.Experience establishing software development lifecycle practices, code-quality standards, CI/CD pipelines, observability, and incident-response processes.Strong project and program management skills, including planning, prioritization, resource allocation, dependency management, and delivery of complex initiatives.Experience collaborating with product, operations, sales, finance, compliance, and executive stakeholders.Ability to balance near-term customer and revenue priorities with long-term platform architecture and technical sustainability.Excellent communication skills, including the ability to explain complex technical decisions, risks, and tradeoffs to nontechnical audiences.Bachelor’s or Master’s degree in Computer Science, Engineering, or a related field, or equivalent practical experience.Preferred QualificationsExperience building products in fintech, payments, banking, lending, or financial infrastructure.Knowledge of payment processing, merchant acquiring, card networks, payment gateways, interchange, card issuing, settlement, or reconciliation.Experience building systems that support high transaction volumes and financial accuracy.Experience integrating with payment processors, banks, enterprise resource planning systems, or other third-party financial platforms.Experience operating within a venture-backed or rapidly scaling startup.A track record of successfully moving between strategic leadership and hands-on execution.Experience building an engineering function during an early or formative stage of a company’s growth.Why Join FreelyTake on a true founding leadership role with the opportunity to build the engineering organization and culture.Work directly with the CEO and experienced fintech and payments founders.Build mission-critical infrastructure for an underserved $1 trillion-plus industry.Join a company with demonstrated traction, signed customers, and substantial payment volume.Work alongside Mastercard as an investor and strategic partner.Help define a new category of B2B payments.Receive meaningful early-stage equity and the opportunity to create significant long-term value.Operate with substantial ownership, autonomy, and direct influence over the company’s future.Compensation and BenefitsCompetitive executive-level salaryMeaningful early-stage equityGenerous paid time offHigh ownership and autonomyDirect influence over company, product, and technical strategy