Trolley
By Trolley (formerly Payment Rails)
Trolley, formerly known as Payment Rails, is a high-growth Canadian fintech company specializing in global payout automation. Since its inception, the company has positioned itself as the essential infrastructure for the internet economy, specifically serving platforms that manage large networks of non-employee workers. Headquartered in Toronto with a significant presence in Montreal, Trolley has expanded its global footprint with offices in London, Miami, Singapore, and Vilnius. The company is consistently recognized for its innovation, recently featuring in the Deloitte Technology Fast 50 for two consecutive years. Trolley’s strategic vision centers on 'Recipient Operations'—unifying payment, tax, and trust modules into a single, scalable platform that reduces the operational burden on finance teams while improving the experience for recipients worldwide.
Trolley was founded in 2015 by Tim Nixon, who currently serves as the CEO. Nixon’s vision was sparked by the realization that while global commerce was becoming digital and borderless, the financial infrastructure to pay the creators and workers behind these platforms remained antiquated, slow, and expensive. Originally launched as Payment Rails, the company spent its early years building the 'last mile' of global payments. In December 2021, the company underwent a major rebranding to Trolley to reflect its evolution from a simple payment 'rail' to a comprehensive payouts ecosystem. The founding story is characterized by a commitment to solving the specific 'payout-adjacent' problems like tax compliance and identity fraud that often hinder the scaling of digital marketplaces.
Trolley has successfully navigated multiple funding rounds to fuel its rapid expansion. In late 2017, the company closed a $1.1 million angel round featuring former PayPal President Scott Thompson. This was followed by bridge rounds totaling $1.9 million between 2018 and 2020. In December 2021, Trolley secured a $7 million Series A investment led by Pace Capital, with partner Chris Paik joining the board. Most recently, in November 2024, the company announced a massive $23 million USD Series B growth equity round led by Wavecrest Growth Partners. This brings Trolley’s total estimated funding to over $33 million, providing the capital necessary to accelerate product development, particularly in AI-driven automation and deeper global banking integrations.
The Trolley platform is organized into four distinct product lines that work together or as standalone modules. 'Trolley Pay' is the core payout engine, enabling mass payments to 210+ countries via various methods. 'Trolley Tax' is a comprehensive compliance suite that handles digital W-8/W-9 collection, automated withholding, and 1099/1042-S filing for the US, as well as DAC7 reporting for the EU. 'Trolley Trust' provides security and risk management, featuring automated identity verification (IDV), AML screening, and phone verification. Finally, 'Trolley Sync' offers deep integrations with ERP systems like NetSuite, ensuring that all payout and tax data is automatically reconciled with accounting records, thus providing a true 'source of truth' for financial reporting.
Trolley has demonstrated a strong commitment to global expansion, both in its payment network and its physical presence. The company now supports payouts in over 135 currencies across more than 210 regions. Geographically, Trolley has established a global office network to support its diverse client base, with locations in North America (Toronto, Montreal, Halifax, Miami, San Francisco), Europe (London, Vilnius), and Asia (Singapore). The company has recently expanded its compliance offerings to support specific regional regulations such as DAC7 in the European Union and SERR in Australia. While it does not currently have a physical office in the GCC, Trolley fully supports payouts to all GCC nations, including the UAE and Saudi Arabia, with localized banking routes and multi-language recipient support.
In the last 12-18 months, Trolley has released several significant features focused on automation and security. A major highlight is the 'AI-powered invoice ingestion' tool, which automates the extraction of payment data from recipient invoices. The platform also introduced 'Funding via Payment Processors,' allowing US-based merchants to fund their Trolley balance directly from Stripe or Braintree. Other recent updates include enhanced TIN (Taxpayer Identification Number) validation to reduce IRS 'B-notices,' the launch of 'Trolley Plus' for enterprise customers, and modular recipient widgets that allow developers to embed specific pay, tax, or trust components into their own apps. Looking toward 2026, the company has announced plans for instant debit card payouts.
Trolley prides itself on a culture of transparency, customer obsession, and rapid innovation. As a remote-first, globally distributed team, the company emphasizes flexibility and autonomy. Its core values include 'Customer Success,' which is reflected in its high rating and dedicated customer success managers for enterprise clients. The company is also committed to DEI (Diversity, Equity, and Inclusion), ensuring that its workforce reflects the global nature of the 'internet economy' it serves. Employees at Trolley often describe the environment as fast-paced and mission-driven, with a focus on 'raising the bar' for how people are paid globally. The company’s recognition in 'Fastest Growing' lists highlights a culture that rewards performance and impact.
Trolley engages its community through an active developer ecosystem and educational resources. The 'Trolley Developers' blog and comprehensive API documentation serve as a hub for engineers integrating the platform. The company also hosts the 'Payouts Pulse' monthly newsletter and various webinars under the 'Raising the Bar' series, where industry experts discuss trends in fintech and compliance. While it doesn't have a traditional public user forum, Trolley maintains a strong presence at major industry conferences and offers 'Trolley Learning Center' articles to educate finance teams on global tax laws and payment trends. Its commitment to the creator and music industries is further evidenced by partnerships with platforms like SoundCloud and Bandcamp.
