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
• Collaborate with Engineering, Product, and Finance to identify recurring operational patterns and translate them into platform-level improvements that raise the reliability ceiling for the entire system
• Contribute to the growth of our engineering culture by sharing knowledge, participating in code reviews, and proactively identifying opportunities to improve how the team builds, observes, and automates

Qualifications & Requirements

• 3-5 years of experience in a software engineering or engineering-adjacent role with exposure to payment systems, backend services, or data pipelines
• Strong SQL skills, comfortable writing standalone scripts and using AI tools such as Claude Code, Open AI, etc 
• Familiarity with RESTful APIs and backend services, with Node.js and TypeScript experience as a plus
• High autonomy and high accountability, you thrive in fast-moving environments and default to action over escalation

Compensation

We tailor compensation packages based on expertise, years of experience, certifications, and other relevant factors. Our comprehensive benefits and rewards are designed to help you thrive both professionally and personally.

Perks & Benefits

• Unlimited vacation
• Competitive stock option package
• $300 one time WFH stipend
• Top of the line 14" MacBook Pro
• Travel stipend for team off sites
• Medicover Sports Membership

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 full customer lifecycle for enterprise accounts, from identifying the right prospects to navigating complex buying processes
• Guide finance and accounting leaders and their teams through evaluating and adopting a genuinely technical product, translating complexity into clarity
• Lead multi-threaded discovery and executive-level conversations across long sales cycles with multiple stakeholders
• Partner closely with the CEO to build our enterprise go-to-market approach from the ground up
• Collaborate with Product and Engineering as a direct conduit from customers, your field insights should shape what we build
• Drive targeted, strategic outreach to the right customer profiles
• Work with marketing to develop materials and messaging that reflect how enterprise buyers actually think about this problem
• Travel roughly once a month to build relationships with customers and prospects in person
• Be the face of our brand with enterprise buyers: technically credible, deeply empathetic, and sharp on the business problems we solve

Who you are:

• You have 5+ years of experience in enterprise SaaS in a role that requires deep product and technical fluency. This could be solutions engineering, product management, or enterprise sales with a highly technical product
• You've worked on or alongside a complex B2B product and can hold your own in conversations with both technical teams and finance/operations leaders
• You are a self-starter and thrive in and are excited by an ambiguous environment where you can build something from 0-1
• You become an expert in your domain, always seeking to deepen your understanding of the industry and prospects you sell to 
• You are based in NYC or willing to relocate and value the collaboration of building something great together in person
• You think commercially: you understand how to move enterprise deals forward, build consensus across stakeholders, and create durable customer relationships that grow over time.

Compensation:

• At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The on target earnings for this role ranges $250,000-$300,000 with uncapped commission, and is accompanied by a target equity package and an extensive suite of benefits, including medical, dental, and vision insurance. All figures cited are in USD and pertain to workers located in the United States.
• We understand that each candidate brings a unique combination of skills, experience, and qualifications to the table, which is why we tailor our compensation packages based on factors such as expertise, years of experience, certifications, and other factors.
• Join us in our mission to innovate and excel, knowing that you will be valued and recognized for your job-related knowledge, skills, and experience. Our comprehensive benefits and rewards are designed to help you thrive both professionally and personally, as we work together to shape the future of our industry.

Location:

• This role will be based in New York City and will have a hybrid work model that consists of a combination of onsite (3 days per week) and remote work expectations. This model is designed to provide our employees with an optimal balance between in-person collaboration and the convenience of remote work. We believe this approach fosters a more productive and engaging work environment while supporting our commitment to employee well-being and work-life balance. 
• Please note that the specific onsite and remote work schedule will be established based on the requirements of the role and the needs of the organization, and remain subject to Company discretion.  The Company reserves the right to modify its in-person and remote work policies and expectations.

Benefits & Perks

• Flexible PTO
• Savings and Investments - 401(k) with company match
• Competitive stock option package
• $300 one-time WFH stipend
• Medical, dental, and vision benefits
• Top of the line 14" Macbook Pro
• Wellness stipend
• Travel stipend for team off-sites

**We appreciate candidates who are open and honest about what they’re looking for so we can ensure it’s a fit on both sides.**

Wingspan does not accept agency-provided resumes from recruitment firms we do not partner with, and any unsolicited resumes sent to our job-related emails or staff will not result in charges to Wingspan.

At Wingspan, we are an equal opportunity employer passionately dedicated to fostering a diverse and inclusive workplace. We wholeheartedly believe that embracing diversity of perspectives and backgrounds is essential to building the best products and providing delightful experiences for our users and team members. We are proud to maintain an environment free from discrimination, retaliation, and harassment.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, ancestry, ethnicity, marital status, pregnancy, disability, genetic information, protected veteran status, or any other characteristic protected by law or ordinance. As we strive for excellence, we are committed to ensuring fair employment practices and business dealings and rejecting any form of discrimination or retaliation.  These protections and commitments extend to all management practices and decisions, including recruitment and hiring, appraisal systems, promotions, training, and career development programs. Consistent with these obligations, Wingspan also provides reasonable accommodations to employees and applicants with disabilities and for sincerely held religious beliefs, observances, and practices.

If you would like to request an accommodation as part of the application process, please contact the Wingspan People Team, people-team@wingspan.app.

Join us in our mission to create a company and products we love, as we celebrate our diverse workforce and promote an inclusive work environment that drives innovation and success.

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 deals
• Lead multi-threaded discovery, exec-level conversations, and longer sales cycles
• Help build out our enterprise sales playbook, collaborating closely with the CEO
• Source a portion of your own pipeline through strategic personalized outreach campaigns
• Build a strong relationship with our marketing team to better our demand generation efforts and selling materials 
• Travel as needed to cultivate industry and prospect relationships, typically once per month
• Be the face of our brand, pairing genuine customer empathy with sharp, methodical problem-solving, while building deep credibility with finance and accounting buyers.

Who you are:

• You have 3+ years of experience in an enterprise SaaS sales role, with a track record of exceeding targets and closing six-figure+ ARR deals
• You have experience being one of the earliest salespeople at a startup or building out a new vertical or product at a larger company. 
• You are a self-starter and thrive in and are excited by an ambiguous environment where you can build something from 0-1
• You become an expert in your domain, always seeking to deepen your understanding of the industry and prospects you sell to 
• You are based in NYC or willing to relocate and value the collaboration of building something great together in person
• You collaborate and build relationships internally, from marketing to product, providing insights to better our product and demand generation campaigns
• You have sold into scaling startups and tech companies

Compensation:

• At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The on target earnings for this role ranges $250,000-$300,000 with uncapped commission, and is accompanied by a target equity package and an extensive suite of benefits, including medical, dental, and vision insurance. All figures cited are in USD and pertain to workers located in the United States.
• We understand that each candidate brings a unique combination of skills, experience, and qualifications to the table, which is why we tailor our compensation packages based on factors such as expertise, years of experience, certifications, and other factors.
• Join us in our mission to innovate and excel, knowing that you will be valued and recognized for your job-related knowledge, skills, and experience. Our comprehensive benefits and rewards are designed to help you thrive both professionally and personally, as we work together to shape the future of our industry.

Location:

• This role will be based in New York City and will have a hybrid work model that consists of a combination of onsite (3 days per week) and remote work expectations. This model is designed to provide our employees with an optimal balance between in-person collaboration and the convenience of remote work. We believe this approach fosters a more productive and engaging work environment while supporting our commitment to employee well-being and work-life balance. 
• Please note that the specific onsite and remote work schedule will be established based on the requirements of the role and the needs of the organization, and remain subject to Company discretion.  The Company reserves the right to modify its in-person and remote work policies and expectations.

Benefits & Perks

• Flexible PTO
• Savings and Investments - 401(k) with company match
• Competitive stock option package
• $300 one-time WFH stipend
• Medical, dental, and vision benefits
• Top of the line 14" Macbook Pro
• Wellness stipend
• Travel stipend for team off-sites

**We appreciate candidates who are open and honest about what they’re looking for so we can ensure it’s a fit on both sides.**

Wingspan does not accept agency-provided resumes from recruitment firms we do not partner with, and any unsolicited resumes sent to our job-related emails or staff will not result in charges to Wingspan.

At Wingspan, we are an equal opportunity employer passionately dedicated to fostering a diverse and inclusive workplace. We wholeheartedly believe that embracing diversity of perspectives and backgrounds is essential to building the best products and providing delightful experiences for our users and team members. We are proud to maintain an environment free from discrimination, retaliation, and harassment.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, ancestry, ethnicity, marital status, pregnancy, disability, genetic information, protected veteran status, or any other characteristic protected by law or ordinance. As we strive for excellence, we are committed to ensuring fair employment practices and business dealings and rejecting any form of discrimination or retaliation.  These protections and commitments extend to all management practices and decisions, including recruitment and hiring, appraisal systems, promotions, training, and career development programs. Consistent with these obligations, Wingspan also provides reasonable accommodations to employees and applicants with disabilities and for sincerely held religious beliefs, observances, and practices.

If you would like to request an accommodation as part of the application process, please contact the Wingspan People Team, people-team@wingspan.app.

Join us in our mission to create a company and products we love, as we celebrate our diverse workforce and promote an inclusive work environment that drives innovation and success.

Who We Are

In today’s economy, an increasing number of workers are choosing to freelance. By 2027, half the U.S. workforce will be independent contractors. Yet there is no system of record for this vast self-employed community and the legions of businesses that increasingly rely on it. A new paradigm is needed to accommodate the future of work that is suddenly no longer in the future. That is what Wingspan is building.

Wingspan is the first payroll platform designed specifically for independent contractors and their businesses. We make onboarding, payments, and compliance easy for flexible workforces of all sizes. Whether you’re a one-person business or a large enterprise, Wingspan has you covered.

We’re a Series B startup based in NYC with backing from some of the best VCs and operators around, including Andreessen Horowitz (a16z) and the CEOs and founders of Warby Parker, Harry’s, Allbirds, Invision, and Flatiron Health.

Now we're hiring for you: an ambitious individual ready to help build, design, and take us to the next level.

Are you ready to be part of a team redefining the future of work? Apply now!

What you'll do:

Through rapid experimentation, the Senior Product Marketing Manager will translate market and customer insights into ICP definitions, website positioning, and GTM messaging collateral. In close partnership with Sales, Product and Post-Sales, you’ll lead product launches and lifecycle programs that drive acquisition, activation, retention, and expansion. This role is ideal for a product marketer who gets under the hood to understand how things work and why it matters, is comfortable creating content assets, and operates independently while knowing when to escalate. You’ll be integral in driving growth, enabling sales, and increasing product adoption and usage. 

Develop Customer Insights: Own qualitative, quantitative, and competitive research; rapidly translate findings into ICP definitions and actionable programs.

• • Conduct a win/loss analysis from the prior data. 
  • Collaborate and experiment on ABM and outbound campaign messaging.
  • Refine our ICP definitions and messaging based on learnings from these efforts and customer interviews.

Refresh Messaging and Positioning: Launch industry messaging campaigns - complete with new web pages, sales collateral, new content (webinars, blogs, etc), and customer case studies. Review and update the competitor analysis.

• • Content and Thought leadership: Partner with Demand Gen Marketing leader and co-founders to develop thought-leadership pieces for marketing and sales-led campaigns.  
  • Author at least 2 content pieces per month, including but not limited to blogs, web pages, webinars, one-pagers, customer case studies

Enablement: Help Sales and Post-Sales advance conversations with sales collateral including decks, one-pagers and case studies.

Product Launch Management:

• • Lead quarterly product releases - inclusive of sales and post-sales enablement, customer-facing materials, and messaging and positioning for all feature releases.
  • Follow established product launch level guidelines to develop and drive GTM plans for any Tier 1 launches. 

Growth programs: Partner with Product, Post-Sales, and Support to design and execute lifecycle programs across email, text, and web to engage current customers and end-user contractors. 

Qualifications

• Customer Empathy: You are passionate about talking to customers and translating their needs into compelling messaging.
• B2B Fintech or HR Tech Expertise: You have an understanding of the complexities of payroll, payments, tax compliance, and employee classification.
• Startup DNA: You are scrappy, biased for action, and have experience working in fast-paced, high-growth startup environments.
• Metrics-Driven & Revenue Minded: You are obsessed with the "why" behind the data and have experience owning and driving commercial outcomes (revenue, monetization, adoption).
• Bonus points if you are:
• A great writer, and interested in creating content
• Personally familiar with the challenges of being an independent contractor or freelancer.

Requirements

• 7+ years of Product Marketing Management experience, with a proven track record of creating collateral and influencing messaging and campaigns.
• B2B SaaS experience
• Excellent verbal and written communication skills, with experience translating features into benefits for multiple audiences
• Be able to leverage data to proactively identify opportunities and drive impactful results
• Must be authorized to work in the United States. 

Compensation

• At Wingspan, we pride ourselves on offering a competitive and comprehensive compensation package that reflects our commitment to attracting top talent. The annual base salary for this role ranges from $150k - $175k, and is accompanied by a target equity package and an extensive suite of benefits, including medical, dental, and vision insurance. All figures cited are in USD and pertain to workers located in the United States.
• We understand that each candidate brings a unique combination of skills, experience, and qualifications to the table, which is why we tailor our compensation packages based on factors such as expertise, years of experience, certifications, and other factors.
• Join us in our mission to innovate and excel, knowing that you will be valued and recognized for your job-related knowledge, skills, and experience. Our comprehensive benefits and rewards are designed to help you thrive both professionally and personally, as we work together to shape the future of our industry.

Benefits & Perks

• Unlimited vacation
• Competitive stock option package
• $300 one-time WFH stipend
• Medical, dental, and vision benefits
• Top of the line 14" Macbook Pro
• Travel stipend for team off-sites
• 401k Matching
• Wellhub, fitness benefit

**We appreciate candidates who are open and honest about what they’re looking for so we can ensure it’s a fit on both sides.**

Wingspan does not accept agency-provided resumes from recruitment firms we do not partner with, and any unsolicited resumes sent to our job-related emails or staff will not result in charges to Wingspan.

At Wingspan, we are an equal opportunity employer passionately dedicated to fostering a diverse and inclusive workplace. We wholeheartedly believe that embracing diversity of perspectives and backgrounds is essential to building the best products and providing delightful experiences for our users and team members. We are proud to maintain an environment free from discrimination, retaliation, and harassment.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, ancestry, ethnicity, marital status, pregnancy, disability, genetic information, protected veteran status, or any other characteristic protected by law or ordinance. As we strive for excellence, we are committed to ensuring fair employment practices and business dealings and rejecting any form of discrimination or retaliation.  These protections and commitments extend to all management practices and decisions, including recruitment and hiring, appraisal systems, promotions, training, and career development programs. Consistent with these obligations, Wingspan also provides reasonable accommodations to employees and applicants with disabilities and for sincerely held religious beliefs, observances, and practices.

If you would like to request an accommodation as part of the application process, please let us know in your submission.

Join us in our mission to create a company and products we love, as we celebrate our diverse workforce and promote an inclusive work environment that drives innovation and success.

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