Job Description
TRAILD: Who are we?
TRAILD is a dynamic, fast-growing SaaS company that streamlines, automates and protects Accounts Payable.
Just as your bank provides always on risk protection for your credit card, TRAILD provides a similar level of security to help businesses protect their B2B payments from fraud, errors and mistakes.
Our specialised Accounts Payable software integrates with leading business ERP systems like SYSPRO, Acumatica, MYOB, and IFS to help clients make their AP process more streamlined, automated and secure.
We have a rapidly growing client base, so you are about to board the rocket ship at the right time. This is an opportunity to make a real impact and with your help we can support more businesses digitise their existing operations with enhanced automation and security.
Hear how TRAILD customers speak about us here.
The Role: Want to be a part of our exciting growth journey?
We are looking for a talented, pragmatic, and business-minded Legal Counsel – Product & Regulatory to join our global team. You will play a critical role in building and scaling TRAILD’s legal and compliance frameworks, partnering closely with cross-functional teams to ensure we meet regulatory requirements while enabling rapid innovation and growth.
Key Responsibilities
Build out product and regulatory legal frameworks from scratch, working independently and in partnership with cross-functional, global teams.
Establish systems for the review of new features and products for compliance with applicable laws and regulations (tech, data, financial services).
Design and implement scalable compliance frameworks and processes, with a particular focus on global privacy and data flows (GDPR, CCPA/CPRA, PIPEDA, APP, POPI, etc.).
Manage global financial services licensing and other regulatory obligations related to financial services and payment processing, including compliance with AML, CTF, BSA, Sanctions regulations and more.
Monitor emerging legal and regulatory developments and translate them into practical policies, guidance, and product requirements.
Manage and coordinate external counsel in multiple jurisdictions to deliver coherent, business-ready compliance advice.
Draft and negotiate customer and vendor contracts, including SaaS agreements, DPAs and other commercial contracts.
Develop and deliver training programs that build organizational capacity for compliance across teams.
Act as a trusted, pragmatic advisor, balancing legal risk with business goals in a fast-paced, hyper-growth environment.
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
Flexibility: we offer a range of remote, hybrid and flexible working options.
Global team: we are growing across APAC, NA and EMEA and have team all across the world.
We are growing at an exponential rate, this is an opportunity to get involved with a true rocketship with all the excitement and opportunities that comes with it
Our team genuinely loves working at TRAILD: we scored a 85 on our 2026 eNPS survey.
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 within the stated range to reflect the candidate’s qualifications and market conditions in their area.
