Description:

TRAILD: Who are we?
At TRAILD, we're on a mission to make business payments as safe, seamless, and automated as consumer payments. Just as your bank protects every credit card swipe, TRAILD protects businesses from fraud, errors, and mistakes every time they pay a supplier.

We're a fast-growing SaaS company reinventing how Accounts Payable is done. Our specialised software integrates with leading ERP systems — including SYSPRO, Acumatica, MYOB, and IFS — to help finance teams streamline processes, boost automation, and unlock enterprise-grade security.

With a rapidly expanding global client base, we're at a scale-up inflection point. Joining TRAILD now means stepping onto a rocket ship 🚀 — with the chance to shape how we grow, innovate, and protect the financial future of businesses worldwide.

Hear what our customers are saying about the impact of TRAILD here (https://www.youtube.com/watch?v=bLuUrJr9VuM).

The Role: Want to be a part of our exciting growth journey?
We're looking for a Legal Counsel – Product & Regulatory who wants more than a traditional legal seat — this is a chance to become a builder at the intersection of law, product and compliance.

You'll be instrumental in scaling TRAILD's legal and compliance frameworks globally, shaping the way we launch products, manage regulatory obligations, and engage with customers across multiple markets. This isn't about saying “no” — it's about enabling innovation at speed while designing the legal infrastructure that will support a category-defining company.

If you're pragmatic, commercially sharp, and thrive in high-growth, high-impact environments, this is your opportunity to make a lasting mark.

Key Responsibilities:

Build from the ground up: Create scalable product and regulatory legal frameworks that keep pace with global growth, working independently and in partnership with cross-functional, global teams.
Shape our licensing strategy: Lead financial services licensing and regulatory obligations worldwide, including AML, CTF, BSA, sanctions regimes and more.
Partner with product: Establish agile systems to review features and launches, ensuring compliance across tech, data, and financial services.
Design compliance engines: Build scalable privacy and data frameworks across GDPR, CCPA/CPRA, PIPEDA, APP, POPI, and emerging regimes.
Future-proof TRAILD: Track and interpret evolving regulations, turning them into practical guidance and product-ready solutions.
Work globally: Manage and coordinate external counsel across jurisdictions, aligning advice into clear, business-ready strategies.
Close deals: Draft and negotiate customer and vendor contracts, including SaaS agreements, DPAs, and commercial partnerships.
Enable the business: Deliver training and guidance that empowers teams to make informed, compliant decisions.
Build trust: Operate as a trusted advisor who balances risk with opportunity in a fast-moving, hyper-growth environment.

Job Requirements:
Who You Are: (include required qualifications, experience, education)

Qualified lawyer in the United States or Canada -JD, LL.B., or equivalent degree
Admitted to the bar and in good standing or otherwise authorized to practice law (e.g. have registered in-house status)
5+ years of payments / fintech legal experience, with a combination of law firm (required) and in-house (preferred) experience.
Strong background in product legal reviews for technology / SaaS companies.
Hands-on experience designing and managing global privacy/data protection compliance programs.
Familiarity with financial services regulations and demonstrated ability to manage compliance requirements and external advisors across multiple jurisdictions.
Skilled in commercial contracting and able to flex into customer/vendor negotiations.
Track record of building compliance systems, policies and organizational frameworks rather than just providing point advice.
Excellent communication skills with the ability to educate, influence, and train cross-functional teams.
Comfortable operating in a dynamic, fast-paced environment with a proactive, problem-solving mindset.
Strong collaborator with an attitude embracing growth, hands-on execution, adaptability, and the scale-up spirit

The Perks of Working at TRAILD

Ride the rocket ship 🚀: We're scaling at exponential speed. That means exciting challenges, outsized opportunities, and the chance to leave your mark on a company in hyper-growth.
Work your way: Whether remote, hybrid or flexible, we trust you to choose how and where you work best.
Join a truly global team: With teammates across North America, APAC, and EMEA, you'll collaborate with diverse, talented people solving big problems together.
A place people love to work: Our team gave TRAILD an outstanding 85 eNPS in 2025.

Please note that the final applicants for this job will be asked to consent in writing to a police check / criminal background check to the extent permitted by law in your jurisdiction of employment.

The base salary range for this position is:

U.S. Candidates: USD $150,000- $190,000 per year
Canadian Candidates: CAD $115,000 - $160,000 per year

Compensation is determined based on experience, education, and geographic location. The final offer may vary to reflect the candidate's qualifications and market conditions in their area.

In addition to salary, you'll also have the opportunity to participate in TRAILD's Employee Share Option Plan (ESOP) — giving you a direct stake in the success of the company you're helping to build.