Chief Compliance Officer, Canada

  • Toronto, Canada
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

We are looking for a regional Chief Compliance Officer to join our team in Toronto, reporting into the global Compliance function and local Board of Directors. A successful candidate will be responsible for leading all compliance management activities relating to conduct risk, regulatory and money laundering/terrorist financing risk for Canada. They will work as an integrated part of our global Compliance team, leveraging the broader organisation and resources to embed a compliance culture locally, design and maintain a compliance framework that meets compliance with local, national, or cross-border laws, rules, regulations, as well as internal policies and procedures. The CCO will help protect Square’s reputation by managing compliance risk across products, business lines, and geographies, supported by globally consistent systems, processes and operational support. 

This role is key to Square's success in the region and will work with colleagues across Compliance, Payments and Industry Relations, Finance, Risk, Counsel, Internal Audit, Product, and Sales and Marketing. The role will necessitate developing relationships with these key stakeholders, informing senior management of significant compliance matters that require attention or action, and dynamically supporting a growing and innovative business. In this role you will have the opportunity to use your compliance experience to solve challenging business problems, find better ways of doing things, and lead meaningful change through technology enablement and scalability. This position is full-time and based in Toronto.

You will:

  • Serve as the Canadian Chief Compliance Officer (CCO) Act as the compliance point of contact with the regulatory agencies for compliance issues, working closely with Legal, and liaise with financial institution partners and card networks, Evaluate business processes and procedures to identify compliance risks and make recommendations to address them
  • Analyse, communicate jurisdictional regulation and best practice, and help design Compliance requirements for new products and services alongside the Compliance Product Advisory team
  • Set and execute strategic, tactical, and operational objectives according to timelines and budget
  • Facilitate regulatory monitoring, risk assessments, analyse and prepare reports for senior management and the Board of Directors, and undergo audits with the support of the Compliance Governance team 
  • Ensure that global policies, standards and processes are applied, and suitable addenda and supplementary procedures and training is developed and maintained for compliance with applicable jurisdictional laws and regulations
  • Investigate and respond to compliance risk issues, regulatory inquiries, including preparing required documentation and making recommendations to senior management on how to proceed


  • A minimum of 8 years of experience in a complex, financial services firm, or related e-money/payments industry with proven experience to operate at a CCO level 
  • Strong technical knowledge of compliance regulations and requirements, risk and typologies
  • Preference for professionals known to and/or with experience dealing with local regulators including FINTRAC (Financial Transactions and Reports Analysis Centre of Canada), the Office of the Superintendent of Financial Institutions Canada ("OSFI"), the Canada Deposit Insurance Corporation ("CDIC"); the Financial Consumer Agency of Canada ("FCAC"); and/or the Ontario Securities Commission.
  • Several years people management experience, preference for experience leading junior managers 
  • Excellent communication skills, written and verbal, to senior management level
  • Ability to build strong working relations with peers, colleagues and with remote based teams with individuals at all levels of the organization
  • Positive outlook and flexibility to handle change, including need for exceptional effort as required

Additional Information

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at) We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.