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VP, Payments

📍 Canada

Technology Upwork

Job Description

Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.

Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn , Facebook , Instagram , TikTok , and X ; and learn more about Lifted at Go-Lifted and follow on LinkedIn .

As VP of Payments, you will define and lead Upwork’s global payments strategy across a high-velocity, two-sided marketplace. Reporting directly to Upwork’s Chief Operating Officer, you will own the vision, operations, and innovation roadmap for a financial system that powers millions of client-freelancer transactions each year. This is a rare opportunity to lead a high-impact function critical to platform trust, liquidity, and growth—while shaping the future of payments and embedded financial services at the world’s work innovation platform.

You will lead cross-functional teams spanning Payments and Tax, Product, Engineering, and Compliance, to transform our financial infrastructure, elevate global payouts, and deliver seamless customer experiences. If you're ready to architect scalable payment systems, forge global partnerships, and drive strategic growth, we invite you to build with us.

Responsibilities

Set the vision and long-term strategy for Upwork’s global payments and financial infrastructure, aligning with company-wide objectives and board-level outcomes

Lead a multi-functional organization responsible for payment rails, payout orchestration, regulatory compliance, risk mitigation, and customer experience

Identify and scale global payment partnerships across acquiring, disbursing, and embedded finance—ensuring resilience, speed, and customer delight

Drive the adoption of AI-powered payment solutions and automation to reduce costs, enhance decision-making, and improve customer outcomes

Serve as executive sponsor for critical financial partnerships, vendor relationships, and compliance frameworks across jurisdictions

Navigate a complex regulatory landscape and ensure Upwork remains ahead of evolving global fintech requirements and risk standards

Deliver measurable outcomes tied to margin optimization, transaction costs and losses, and the optimal balance between payment success rates and net transaction loss, while ensuring experience quality

Build, mentor, and inspire a high-performing leadership team within the Payments function, reinforcing a culture of excellence, innovation, and cross-functional alignment

What it takes to catch our eye

Proven executive leadership experience owning global payments, payout systems, or embedded finance platforms at scale—preferably within a two-sided marketplace or fintech environment

Deep understanding of financial systems, cross-border payment rails, wallet infrastructures, and regulatory dynamics across key regions (e.g., US, EMEA, APAC, LATAM)

Track record of driving strategic transformation, product portfolio management, and executing through complex, matrixed organizations

Proficiency in leveraging AI to optimize financial workflows, increase operational efficiency, and accelerate partner evaluation or integration processes

Ability to influence at all levels, from board to technical teams, and to balance long-term strategic vision with near-term executional excellence

Come

change how the world works. At Upwork, you’ll shape the future of work for a global, remote-first workforce, creating economic opportunities for professionals worldwide. While we have a physical office in Palo Alto, we currently hire full-time employees in 34 U.S. states, making it easier than ever to join our mission from wherever you call home.

Our culture is built on trust, risk-taking, customer focus, and excellence, all in service of our core mission: to create economic opportunities so people have better lives. We embrace authenticity and inclusion, encouraging everyone to bring their whole selves to work. Personal and professional growth is a priority here, supported through development programs, mentorship, and our Upwork Belonging Communities.

We’re proud to offer benefits that go beyond the basics, including comprehensive medical coverage for you and your family, unlimited PTO, a 401(k) plan with matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan. Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.

Ready to help shape the future of work? Check out our Careers page to learn more about opportunities at Upwork.

The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.

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Job Details

Posted Date: February 28, 2026
Job Type: Technology
Location: Canada
Company: Upwork

Ready to Apply?

Don't miss this opportunity! Apply now and join our team.