Head of 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

Square is entering the next stage of growth in Canada. The company launched its payments operations in the Canada in 2013 and wants to build on current success and accelerate growth across the Square ecosystem of products. The Head of Canada will report to CMO at Square.  He/she will be tasked with growing Square in Canada. He/she will also be collaborating with Square headquarters on everything from government relations to bank relationships to product development to go-to-market strategies.

Specific responsibilities include:

  • Manage the overall business strategy and P&L for Square in Canada

  • Build and lead Canadian business teams including sales, marketing and business development

  • Develop partnerships with financial institutions (e.g., banks and networks), local organizations, and sellers to drive Square’s business strategy

  • Lead go-to-market strategies and plans for Square’s products and services

  • Collect country customer insights to inform Square’s global product roadmap

  • Communicate with governments and regulators to ensure acceptance for Square’s products

  • Act as a key member of the global Square management team






The ideal candidate will be a seasoned internet executive, preferably with some startup experience, in roles with accountability in general management, sales, marketing and/or business development. Understanding of fintech, payments or mPOS is a plus. The ideal candidate will understand the consumer internet ecosystem and will bring fresh, innovative thinking. The candidate needs to have a strong understanding of the Canadian market. This role is based in Toronto but will require regular periodic global travel.

From a functional point of view, the ideal candidate is a proven general manager. He/she will be adept at defining a business opportunity as well as the successful strategies to deliver on that opportunity. Importantly, he/she will also be skilled at translating these business strategies into insights that will help inform the regional and country go to market strategies. He/she will understand how to build a brand along with acquiring and growing an engaged customer base. Experience in business development and dealing with partners is also very important as well. The ideal combination will be someone whose general management experience spans strategy, sales, marketing and business development. It is likely that the successful candidate will have blue chip operating experience or experience in scaling an innovative technology player as well as a phase of consulting from a leading management consulting.

On a personal level the ideal candidate will be smart and analytical. He/she will be strategically strong but also be comfortable with the detail and able to alternate seamlessly between the two. In this way he/she will have ‘breadth and depth.’ He/she will have also strong leadership and influencing skills for both external and internal stakeholders. He/she focuses on getting things done thoughtfully and quickly with a data-driven approach. Finally, he/she will have the drive, resilience, inspirational nature and "will to win" to advance Square’s leadership position in Canada.

In terms of the performance and personal competencies required for the position, we would highlight the following:

Setting Strategy

  • Develops clear, compelling, and ultimately successful new strategies to drive growth

  • Possesses the self-confidence and unique insight required to navigate through ambiguity; constructively challenge conventional wisdom

  • Prioritizes and organizes investment/resources against highest return opportunities through structured, process-driven approach

  • Able to effectively articulate direction and make case for incremental investment based on shifting landscape, priority markets, and financial opportunity

Building Relationships, Using Influence

  • Possesses a partnership mentality; Builds effective relationships and motivates others to pursue common objectives and goals

  • Demonstrates a high impact, persuasive personality; builds and sustains important internal and external relationships

  • Outstanding communicator, collaborator, and consultative partner able to engage easily; builds rapport quickly

  • Proven ability to impact business decisions as a member of the leadership team

  • Proven ability to engage effectively with key regulators and government officials

Business Acumen

  • A proven and recognized leader with a track record of creating growth opportunities and developing new partnerships which deliver growth and financial return

  • Anticipates future business opportunities (or problems) and develops strategies to address them; can take business to “the next level”

  • Uses data to prioritize and make well-informed decisions; deftly manages risk while seeking strong financial return

  • Responds to changing trends and new technologies to leverage new market opportunities and implement new partnerships

  • Understands challenges, opportunities and the competitive landscape; Strong record of achievement in applying a customer mindset to shape solutions and approaches and to realize marketplace potential/achieve financial goals

Executing for Results

  • Strong execution focus with track record for accelerating growth and new market development through partnership development

  • Results-oriented individual with a history of setting and achieving goals over and above, establishing and meeting aggressive timelines, and achieving outstanding performance

Leading Teams/Collaboration

  • Creates loyalty, trust and following; can energize people and teams, foster team’s professional development, and make cross-functional cooperation happen

  • Recognizes and utilizes the strengths of key players; attracts the best and brightest talent to the organization; holds people accountable for agreed-to results

  • Creates support and buy-in across a wide range of stakeholders; creates a strong network of relationships among peers, partners, external constituencies, decision makers and stakeholders

  • Promotes culture of teamwork across organizational boundaries; willing to break down functional silos to optimize business results and encourage the overall growth



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)squareup.com. 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.