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Enterprise Account Executive at Wingspan - New York, NY - Enterprise Account Executive New York, NY Who We Are Wingspan serves independent contractors and the businesses that hire them. Our customers are the backbone of the modern economy and are radically underserved by legacy payroll platforms. Our job is to make working with them effortless. Wingspan is the first payroll platform built specifically for the independent workforce. We're different because of our end-to-end contractor management: seamless onboarding, automated payments, and built-in compliance, all in one place, for flexible workforces of any size. That's why the businesses that rely on contractors trust Wingspan to handle the complexity so they don't have to. This market is massive and ours to define. By 2027, half the U.S. workforce will be independent contractors, and we're the system of record they've never had. We're a Series B company backed by Andreessen Horowitz (a16z) and the founders and CEOs of Warby Parker, Harry's, Allbirds, Invision, and Flatiron Health. Enterprise Account Executive This is a 0-to-1 role. As our first Enterprise AE, you'll own the full sales lifecycle, build the playbook alongside the CEO, and work hand-in-hand with Product and Engineering to make sure we're delivering for our largest customers. There's no inherited process or predefined territory, you'll be the one defining how Wingspan wins in the enterprise market. If you're the type of seller who'd rather architect something than inherit it, this role is for you. What you'll do: - Own the full-cycle sales lifecycle for enterprise accounts, from prospecting to closing - Close six-figure+ ARR

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Strategic Enterprise Account Executive at Wingspan - New York, NY - Strategic Enterprise Account Executive New York, NY Who We Are Wingspan serves independent contractors and the businesses that hire them. Our customers are the backbone of the modern economy and are radically underserved by legacy payroll platforms. Our job is to make working with them effortless. Wingspan is the first payroll platform built specifically for the independent workforce. We're different because of our end-to-end contractor management: seamless onboarding, automated payments, and built-in compliance, all in one place, for flexible workforces of any size. That's why the businesses that rely on contractors trust Wingspan to handle the complexity so they don't have to. This market is massive and ours to define. By 2027, half the U.S. workforce will be independent contractors, and we're the system of record they've never had. We're a Series B company backed by Andreessen Horowitz (a16z) and the founders and CEOs of Warby Parker, Harry's, Allbirds, Invision, and Flatiron Health. Strategic Enterprise Account Executive This is a 0-to-1 role for someone who's spent years close to a complex enterprise product and knows how to translate that depth into customer trust. As our first enterprise hire on the commercial side, you'll shape how we go to market and work shoulder-to-shoulder with the CEO, Product, and Engineering to make sure what we're building actually delivers. There's no inherited playbook, you'll help write it. If you'd rather be the expert in the room than the rep in the room, this role is for you. What you'll do: - Own the

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Software Engineer, Payment Operations at Wingspan - Warsaw, Poland - Software Engineer, Payment Operations Warsaw, Poland Who We Are Wingspan is the first payroll platform designed specifically for independent contractors and their businesses. We simplify onboarding, payments, and compliance for flexible workforces of all sizes, from solo operators to large enterprises. We're a Series B startup based in NYC with distributed teams in the USA, Poland, and the UK, and backed by Andreessen Horowitz (a16z), Touring Capital, and a strong network of operators, including the CEOs and founders of Warby Parker, Harry's, Allbirds, Invision, and Flatiron Health. About the Role As a Software Engineer on the Payment Operations team, you will be responsible for the execution layer that ensures every dollar on Wingspan's platform is accounted for, reconciled, and moved accurately on time. You will have direct access to production systems, a mandate to identify what's broken or inefficient, and the authority to engineer the fix. This role reports to the Head of Payments & Compliance Operations and is based in Warsaw, Poland, with a remote work model. What You'll Do - Design, develop, and ship internal systems and automation that eliminate entire categories of operational toil, owning every problem end-to-end from initial diagnosis to permanent fix - Build and maintain reconciliation infrastructure that keeps Wingspan's ledger, bank records, and platform transaction data in continuous alignment, automatically and at scale - Develop monitoring and alerting systems that surface funding health issues and payment anomalies in real time, ensuring problems are caught and resolved before they ever reach a customer -

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Engineering Lead Platform at Wingspan - New York, NY - Engineering Lead Platform New York, NY Wingspan Networks, Inc. seeks an Engineering Lead Platform in New York, NY to Design, develop, and implement high-quality, scalable software solutions that meet client needs and exceed expectations;Collaborate with cross-functional teams to ensure seamless integration and timely delivery of projects; Continuously improve and optimize existing software systems by identifying inefficiencies, refactoring code, and implementing best practices; Participate in agile development processes, including sprint planning, daily standups, and retrospectives, to ensure project success and team alignment; and Contribute to grown of engineering culture by sharing knowledge, mentoring new engineer hires, and actively participating in code reviews and technical discussions. Telecommuting is permitted from anywhere in the U.S. Position requires a Bachelor's degree or foreign equivalent in Computer Systems Engineering, Computer Engineering, or other closely related field, and 3 years of progressive, postbaccalaureate experience in the job offered or related occupation in Software Engineering. Must have 3 years of experience in the following skills: Managing complex projects end-to-end, from initial planning and scoping to successful implementation and delivery, ensuring timely completion and alignment with business objectives; Software testing methodologies, including unit, integration, and system testing; Experience with back-end programming language including Typescript; Experience taking broad product requirements and translating them into specific technical requirements and leading team of Engineers. The salary for this position is $185,000 to $193,930 annual. To apply, send resumes to careers@wingspan.app with ref# TK1025

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